Brutally Anna https://maybeboth.com/ en 2024 Maybe Both Welcome to Brutally Anna — the podcast where we stop pretending we’re fine and start telling the f*cking truth. I’m Anna, a writer, accidental influencer, and self-appointed spokesperson for the women who feel too much, think too hard, and talk to themselves in the shower. This isn’t a self-help podcast. It’s a self-honesty one. Each week, I dive into the mess of being a human — the shame, the silence, the spirals — and say the things we’re all thinking but too afraid to post. From heartbreak to ambition, mental health to creative burnout, loneliness to the urge to completely disappear... nothing is off-limits. If it’s brutally honest, we go there. No fake pep talks. No toxic positivity. Just the deeply uncomfortable, strangely funny, painfully freeing truth. If you’ve ever felt like you’re too much or not enough — you’re in the right place. Pull up a chair. Let’s get brutal. New episodes on Wednesdays. https://megaphone.imgix.net/podcasts/83420e14-8650-11ef-a0de-876679829f72/image/4262f31fe9776e906c7c2e15aa20a84e.jpg?ixlib=rails-4.3.1&max-w=3000&max-h=3000&fit=crop&auto=format,compress Brutally Anna https://maybeboth.com/ episodic Anna Kai Welcome to Brutally Anna — the podcast where we stop pretending we’re fine and start telling the f*cking truth. I’m Anna, a writer, accidental influencer, and self-appointed spokesperson for the women who feel too much, think too hard, and talk to themselves in the shower. This isn’t a self-help podcast. It’s a self-honesty one. Each week, I dive into the mess of being a human — the shame, the silence, the spirals — and say the things we’re all thinking but too afraid to post. From heartbreak to ambition, mental health to creative burnout, loneliness to the urge to completely disappear... nothing is off-limits. If it’s brutally honest, we go there. No fake pep talks. No toxic positivity. Just the deeply uncomfortable, strangely funny, painfully freeing truth. If you’ve ever felt like you’re too much or not enough — you’re in the right place. Pull up a chair. Let’s get brutal. New episodes on Wednesdays. Welcome to Brutally Anna — the podcast where we stop pretending we’re fine and start telling the f*cking truth.

I’m Anna, a writer, accidental influencer, and self-appointed spokesperson for the women who feel too much, think too hard, and talk to themselves in the shower. This isn’t a self-help podcast. It’s a self-honesty one.

Each week, I dive into the mess of being a human — the shame, the silence, the spirals — and say the things we’re all thinking but too afraid to post. From heartbreak to ambition, mental health to creative burnout, loneliness to the urge to completely disappear... nothing is off-limits. If it’s brutally honest, we go there.

No fake pep talks. No toxic positivity. Just the deeply uncomfortable, strangely funny, painfully freeing truth.

If you’ve ever felt like you’re too much or not enough — you’re in the right place. Pull up a chair. Let’s get brutal. New episodes on Wednesdays.

]]> Anna Kai brutallyannapodcast@gmail.com How to Know When to Quit (And When to Keep Going) This week, I’m closing the chapter on Brutally Anna by talking about mile 20—of the New York City Marathon, yes, but also of life. I ran that race back in 2017, and the thing about a marathon is you always know how far you have left. In life, you don’t. And this year felt like mile 23 for me: mentally brutal, spiritually draining, career-wise confusing, and laced with the kind of disappointment that makes quitting look like relief. But pushing through reminded me that the breakthrough always comes after the part where you think you can’t keep going. I get into the messy middle of my career, how I’m retraining my brain, why I’m stepping back from podcasting for now, and why giving up the right things is sometimes the smartest, bravest way to get to your own finish line. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 14 Nov 2025 10:00:00 -0000 full Anna Kai This week, I’m closing the chapter on Brutally Anna by talking about mile 20—of the New York City Marathon, yes, but also of life. I ran that race back in 2017, and the thing about a marathon is you always know how far you have left. In life, you don’t. And this year felt like mile 23 for me: mentally brutal, spiritually draining, career-wise confusing, and laced with the kind of disappointment that makes quitting look like relief. But pushing through reminded me that the breakthrough always comes after the part where you think you can’t keep going. I get into the messy middle of my career, how I’m retraining my brain, why I’m stepping back from podcasting for now, and why giving up the right things is sometimes the smartest, bravest way to get to your own finish line. Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I’m closing the chapter on Brutally Anna by talking about mile 20—of the New York City Marathon, yes, but also of life. I ran that race back in 2017, and the thing about a marathon is you always know how far you have left. In life, you don’t. And this year felt like mile 23 for me: mentally brutal, spiritually draining, career-wise confusing, and laced with the kind of disappointment that makes quitting look like relief. But pushing through reminded me that the breakthrough always comes after the part where you think you can’t keep going. I get into the messy middle of my career, how I’m retraining my brain, why I’m stepping back from podcasting for now, and why giving up the right things is sometimes the smartest, bravest way to get to your own finish line.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1067 The Myth of the Soulmate In today’s episode, I’m talking about why I think the word “soulmate” is kind of bullshit—not because love isn’t real, but because we use that word to trap ourselves in relationships that aren’t actually right for us. I share how I once assigned the title “soulmate” to practically every man I dated in my twenties, what finally shifted when I met my husband, and why I now believe the strongest, healthiest relationships aren’t about fate or twin flames or being “meant to be”—they’re about two people choosing each other on purpose, every day, especially when life gets hard. I also get into how the soulmate label often keeps women stuck, why our culture rewards “pick me” behavior, and how the real work of love is not finding the missing half of your soul, but becoming whole yourself first. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 07 Nov 2025 20:00:00 -0000 full Anna Kai In today’s episode, I’m talking about why I think the word “soulmate” is kind of bullshit—not because love isn’t real, but because we use that word to trap ourselves in relationships that aren’t actually right for us. I share how I once assigned the title “soulmate” to practically every man I dated in my twenties, what finally shifted when I met my husband, and why I now believe the strongest, healthiest relationships aren’t about fate or twin flames or being “meant to be”—they’re about two people choosing each other on purpose, every day, especially when life gets hard. I also get into how the soulmate label often keeps women stuck, why our culture rewards “pick me” behavior, and how the real work of love is not finding the missing half of your soul, but becoming whole yourself first. Learn more about your ad choices. Visit podcastchoices.com/adchoices In today’s episode, I’m talking about why I think the word “soulmate” is kind of bullshit—not because love isn’t real, but because we use that word to trap ourselves in relationships that aren’t actually right for us. I share how I once assigned the title “soulmate” to practically every man I dated in my twenties, what finally shifted when I met my husband, and why I now believe the strongest, healthiest relationships aren’t about fate or twin flames or being “meant to be”—they’re about two people choosing each other on purpose, every day, especially when life gets hard. I also get into how the soulmate label often keeps women stuck, why our culture rewards “pick me” behavior, and how the real work of love is not finding the missing half of your soul, but becoming whole yourself first.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1520 Laziness as a Love Language This week’s episode is about how I think I accidentally found the cure for doom-scrolling: doing nothing—on purpose. Lately I’ve been trying to detach from my phone because I realized that constant productivity and comparison are killing my joy. Somewhere along the way, “rest” got rebranded as “laziness,” especially for women, and I’m done with that. So instead of polishing hardware or checking off my to-do list, I’ve been wandering around HomeGoods, calling it meditation. I talk about how the obsession with progress keeps us on the hamster wheel of capitalism, how my dad can go on a 14-hour flight with nothing but his thoughts, and how learning to simply exist—to be gentle, unproductive, and occasionally stupid in the best way, might actually be the most radical kind of self-care. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 31 Oct 2025 14:00:00 -0000 full Anna Kai This week’s episode is about how I think I accidentally found the cure for doom-scrolling: doing nothing—on purpose. Lately I’ve been trying to detach from my phone because I realized that constant productivity and comparison are killing my joy. Somewhere along the way, “rest” got rebranded as “laziness,” especially for women, and I’m done with that. So instead of polishing hardware or checking off my to-do list, I’ve been wandering around HomeGoods, calling it meditation. I talk about how the obsession with progress keeps us on the hamster wheel of capitalism, how my dad can go on a 14-hour flight with nothing but his thoughts, and how learning to simply exist—to be gentle, unproductive, and occasionally stupid in the best way, might actually be the most radical kind of self-care. Learn more about your ad choices. Visit podcastchoices.com/adchoices This week’s episode is about how I think I accidentally found the cure for doom-scrolling: doing nothing—on purpose. Lately I’ve been trying to detach from my phone because I realized that constant productivity and comparison are killing my joy. Somewhere along the way, “rest” got rebranded as “laziness,” especially for women, and I’m done with that. So instead of polishing hardware or checking off my to-do list, I’ve been wandering around HomeGoods, calling it meditation. I talk about how the obsession with progress keeps us on the hamster wheel of capitalism, how my dad can go on a 14-hour flight with nothing but his thoughts, and how learning to simply exist—to be gentle, unproductive, and occasionally stupid in the best way, might actually be the most radical kind of self-care.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1347 Fertility Math Will Make You Crazy In this episode, I talk about what it’s really been like trying to get pregnant after spending my entire twenties doing everything in my power not to. I share how I went from never tracking my period to obsessing over ovulation sticks and smiley faces, and how coming off Zoloft for the first time in years forced me to actually face my hormones head-on. I get into my PMDD, the endless trial-and-error of antidepressants, the small lifestyle changes that finally helped me feel stable again, and the deeply unsexy logistics of “timed sex.” Mostly, I wanted to be honest about how no one prepares you for how hard this process can be—or how much it messes with your sense of control. It’s equal parts confessional, fertility crash course, and reminder that wanting a baby doesn’t automatically make it easy to have one. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 24 Oct 2025 09:00:00 -0000 full Anna Kai In this episode, I talk about what it’s really been like trying to get pregnant after spending my entire twenties doing everything in my power not to. I share how I went from never tracking my period to obsessing over ovulation sticks and smiley faces, and how coming off Zoloft for the first time in years forced me to actually face my hormones head-on. I get into my PMDD, the endless trial-and-error of antidepressants, the small lifestyle changes that finally helped me feel stable again, and the deeply unsexy logistics of “timed sex.” Mostly, I wanted to be honest about how no one prepares you for how hard this process can be—or how much it messes with your sense of control. It’s equal parts confessional, fertility crash course, and reminder that wanting a baby doesn’t automatically make it easy to have one. Learn more about your ad choices. Visit podcastchoices.com/adchoices In this episode, I talk about what it’s really been like trying to get pregnant after spending my entire twenties doing everything in my power not to. I share how I went from never tracking my period to obsessing over ovulation sticks and smiley faces, and how coming off Zoloft for the first time in years forced me to actually face my hormones head-on. I get into my PMDD, the endless trial-and-error of antidepressants, the small lifestyle changes that finally helped me feel stable again, and the deeply unsexy logistics of “timed sex.” Mostly, I wanted to be honest about how no one prepares you for how hard this process can be—or how much it messes with your sense of control. It’s equal parts confessional, fertility crash course, and reminder that wanting a baby doesn’t automatically make it easy to have one.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1502 Stop Needing A Witness For Your LIfe Somewhere along the way, we started believing that if no one saw it, it didn’t happen — that joy requires an audience and meaning needs proof. In this episode, I talk about the psychological cost of living life through a camera roll: how documenting our memories actually weakens them, how performance has replaced presence, and why so many of our “best days” — including my wedding — end up feeling hollow when we live them for others. From weddings to friendships to social media validation, this is about reclaiming your life from the witnesses. Because the moment doesn’t become real when you post it — it becomes real when you let it belong only to you. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 17 Oct 2025 09:00:00 -0000 full Anna Kai Somewhere along the way, we started believing that if no one saw it, it didn’t happen — that joy requires an audience and meaning needs proof. In this episode, I talk about the psychological cost of living life through a camera roll: how documenting our memories actually weakens them, how performance has replaced presence, and why so many of our “best days” — including my wedding — end up feeling hollow when we live them for others. From weddings to friendships to social media validation, this is about reclaiming your life from the witnesses. Because the moment doesn’t become real when you post it — it becomes real when you let it belong only to you. Learn more about your ad choices. Visit podcastchoices.com/adchoices Somewhere along the way, we started believing that if no one saw it, it didn’t happen — that joy requires an audience and meaning needs proof. In this episode, I talk about the psychological cost of living life through a camera roll: how documenting our memories actually weakens them, how performance has replaced presence, and why so many of our “best days” — including my wedding — end up feeling hollow when we live them for others.

From weddings to friendships to social media validation, this is about reclaiming your life from the witnesses. Because the moment doesn’t become real when you post it — it becomes real when you let it belong only to you.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1468 Everybody Wants A Piece of You I’ve ghosted more people this year than any other year of my life — and I don’t feel bad about it. The truth is, when you start building something of your own, people come crawling out of the woodwork. Old acquaintances suddenly want to “catch up,” but what they really want is a favor, a contact, a shortcut. For a long time, I said yes to everyone because I thought it made me kind. I thought giving without limits was the price of being a good person. But generosity without discernment isn’t kindness — it’s self-abandonment. In this episode, I talk about the difference between being needed and being wanted, and why it’s okay if people think you’re a “shitty person” for having boundaries. Because sometimes protecting your peace means disappointing everyone who only showed up to take a piece of you. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 10 Oct 2025 09:00:00 -0000 full Anna Kai I’ve ghosted more people this year than any other year of my life — and I don’t feel bad about it. The truth is, when you start building something of your own, people come crawling out of the woodwork. Old acquaintances suddenly want to “catch up,” but what they really want is a favor, a contact, a shortcut. For a long time, I said yes to everyone because I thought it made me kind. I thought giving without limits was the price of being a good person. But generosity without discernment isn’t kindness — it’s self-abandonment. In this episode, I talk about the difference between being needed and being wanted, and why it’s okay if people think you’re a “shitty person” for having boundaries. Because sometimes protecting your peace means disappointing everyone who only showed up to take a piece of you. Learn more about your ad choices. Visit podcastchoices.com/adchoices I’ve ghosted more people this year than any other year of my life — and I don’t feel bad about it. The truth is, when you start building something of your own, people come crawling out of the woodwork. Old acquaintances suddenly want to “catch up,” but what they really want is a favor, a contact, a shortcut. For a long time, I said yes to everyone because I thought it made me kind. I thought giving without limits was the price of being a good person. But generosity without discernment isn’t kindness — it’s self-abandonment. In this episode, I talk about the difference between being needed and being wanted, and why it’s okay if people think you’re a “shitty person” for having boundaries. Because sometimes protecting your peace means disappointing everyone who only showed up to take a piece of you.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1524 The Art of Dining Alone (and Redefining Community) This week I’m talking about the art of dining alone, and why sometimes community is just you, your fork, and the courage to sit there unapologetically. Spoiler: I went out for sushi by myself, got seated in the middle of strangers’ dates, and somehow ended up in an accidental fake date with a man named Brad. We’ll also get into why friendships fade, why I don’t want a “big circle,” and why a Friday night on the couch with Dave, Sawyer, and Dateline might be the ultimate dinner party. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 03 Oct 2025 09:00:00 -0000 full Anna Kai This week I’m talking about the art of dining alone, and why sometimes community is just you, your fork, and the courage to sit there unapologetically. Spoiler: I went out for sushi by myself, got seated in the middle of strangers’ dates, and somehow ended up in an accidental fake date with a man named Brad. We’ll also get into why friendships fade, why I don’t want a “big circle,” and why a Friday night on the couch with Dave, Sawyer, and Dateline might be the ultimate dinner party. Learn more about your ad choices. Visit podcastchoices.com/adchoices This week I’m talking about the art of dining alone, and why sometimes community is just you, your fork, and the courage to sit there unapologetically. Spoiler: I went out for sushi by myself, got seated in the middle of strangers’ dates, and somehow ended up in an accidental fake date with a man named Brad. We’ll also get into why friendships fade, why I don’t want a “big circle,” and why a Friday night on the couch with Dave, Sawyer, and Dateline might be the ultimate dinner party.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1362 Everybody's Dying - Here's How It Taught Me To Live It’s been a couple months since I dropped into your ears, and I wanted to be honest about where I’ve been. I hit pause on podcasting to rethink my career, launch my Substack (maybe both), and figure out if this mic was really the best place for me to share. In that break, I realized two things: one, I hate editing video clips more than anything in the world, and two, I still love the freedom of just talking to you like this. So, I’m back for an eight-episode run—no promises beyond that, but I’ll be upfront with you when we get to the end. Today’s episode is about death and how losing people too soon has reshaped the way I live. I talk about stripping away the performance in friendships, birthdays, even social media, and focusing on the quiet, un-Instagrammable parts of life that actually make it worth living. If you’ve ever felt caught in the grind of “what’s next,” this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices Fri, 26 Sep 2025 09:00:00 -0000 full Anna Kai It’s been a couple months since I dropped into your ears, and I wanted to be honest about where I’ve been. I hit pause on podcasting to rethink my career, launch my Substack (maybe both), and figure out if this mic was really the best place for me to share. In that break, I realized two things: one, I hate editing video clips more than anything in the world, and two, I still love the freedom of just talking to you like this. So, I’m back for an eight-episode run—no promises beyond that, but I’ll be upfront with you when we get to the end. Today’s episode is about death and how losing people too soon has reshaped the way I live. I talk about stripping away the performance in friendships, birthdays, even social media, and focusing on the quiet, un-Instagrammable parts of life that actually make it worth living. If you’ve ever felt caught in the grind of “what’s next,” this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices It’s been a couple months since I dropped into your ears, and I wanted to be honest about where I’ve been. I hit pause on podcasting to rethink my career, launch my Substack (maybe both), and figure out if this mic was really the best place for me to share. In that break, I realized two things: one, I hate editing video clips more than anything in the world, and two, I still love the freedom of just talking to you like this.

So, I’m back for an eight-episode run—no promises beyond that, but I’ll be upfront with you when we get to the end. Today’s episode is about death and how losing people too soon has reshaped the way I live. I talk about stripping away the performance in friendships, birthdays, even social media, and focusing on the quiet, un-Instagrammable parts of life that actually make it worth living.

If you’ve ever felt caught in the grind of “what’s next,” this one’s for you.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1444 Why Women Stay Too Long—and How to Stop This week, I respond to a listener who knows her marriage is over—but can’t shake the guilt of being the one to end it. We talk about why women are taught to feel like the villain when they choose themselves, how shame is inherited, and what it really means to leave a life that was never built for you. If you’ve ever thought, “But he’s not that bad,” or “Who will I be if I walk away?”—this one’s for you. Also: why toilet paper holders are a metaphor for personal growth. Sort of. Just listen. ALL MY CHANNELS Newsletter: https://maybeboth.substack.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Wed, 16 Jul 2025 22:19:00 -0000 full Anna Kai This week, I respond to a listener who knows her marriage is over—but can’t shake the guilt of being the one to end it. We talk about why women are taught to feel like the villain when they choose themselves, how shame is inherited, and what it really means to leave a life that was never built for you. If you’ve ever thought, “But he’s not that bad,” or “Who will I be if I walk away?”—this one’s for you. Also: why toilet paper holders are a metaphor for personal growth. Sort of. Just listen. ALL MY CHANNELS Newsletter: https://maybeboth.substack.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I respond to a listener who knows her marriage is over—but can’t shake the guilt of being the one to end it. We talk about why women are taught to feel like the villain when they choose themselves, how shame is inherited, and what it really means to leave a life that was never built for you.

If you’ve ever thought, “But he’s not that bad,” or “Who will I be if I walk away?”—this one’s for you.

Also: why toilet paper holders are a metaphor for personal growth. Sort of. Just listen.


ALL MY CHANNELS Newsletter: https://maybeboth.substack.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth


Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1033 He’s Great—Except for the Part Where He Lies to Me This week’s episode is brought to you by: the delusion that a man who lies to you repeatedly is still somehow “99% amazing.” In this episode, I unpack: Why 99% perfect still isn’t enough when the other 1% is gaslighting What it really means when you say “he’s so great, except…” Why “second chances” are often just “I’m scared to be alone” in a trench coat The emotional equivalent of playing a rigged slot machine with your self-worth And how to know when you’re not actually confused — you’re just stalling If you’re currently debating whether to leave a man who keeps texting other women — this episode is for you. Because you deserve more than 99%. You deserve 100%, or at the very least, a boyfriend who doesn’t flirt with married women behind your back. ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 10 Jul 2025 01:16:00 -0000 full Anna Kai This week’s episode is brought to you by: the delusion that a man who lies to you repeatedly is still somehow “99% amazing.” In this episode, I unpack: Why 99% perfect still isn’t enough when the other 1% is gaslighting What it really means when you say “he’s so great, except…” Why “second chances” are often just “I’m scared to be alone” in a trench coat The emotional equivalent of playing a rigged slot machine with your self-worth And how to know when you’re not actually confused — you’re just stalling If you’re currently debating whether to leave a man who keeps texting other women — this episode is for you. Because you deserve more than 99%. You deserve 100%, or at the very least, a boyfriend who doesn’t flirt with married women behind your back. ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices This week’s episode is brought to you by: the delusion that a man who lies to you repeatedly is still somehow “99% amazing.”

In this episode, I unpack:

  • Why 99% perfect still isn’t enough when the other 1% is gaslighting

  • What it really means when you say “he’s so great, except…”

  • Why “second chances” are often just “I’m scared to be alone” in a trench coat

  • The emotional equivalent of playing a rigged slot machine with your self-worth

  • And how to know when you’re not actually confused — you’re just stalling

If you’re currently debating whether to leave a man who keeps texting other women — this episode is for you. Because you deserve more than 99%. You deserve 100%, or at the very least, a boyfriend who doesn’t flirt with married women behind your back.


ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth


Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1655 Life’s Too Short to Be Uncomfortable, Emotionally or In a Thong Let’s talk about thongs, grief, people-pleasing, and the radical act of not going to the damn party. In this episode, I unravel why I stopped molding myself into someone else’s ideal — whether it was for a man, a friend, or an aesthetic. I also talk about loss, what a photographer taught me about timing, and why your “no” doesn’t need an excuse (or a follow-up text). If you’ve ever contorted yourself to be chosen, approved of, or invited — this one's for you. Also, RIP to the thong I wore once in 2014. ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Wed, 02 Jul 2025 17:35:00 -0000 full Anna Kai Let’s talk about thongs, grief, people-pleasing, and the radical act of not going to the damn party. In this episode, I unravel why I stopped molding myself into someone else’s ideal — whether it was for a man, a friend, or an aesthetic. I also talk about loss, what a photographer taught me about timing, and why your “no” doesn’t need an excuse (or a follow-up text). If you’ve ever contorted yourself to be chosen, approved of, or invited — this one's for you. Also, RIP to the thong I wore once in 2014. ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Let’s talk about thongs, grief, people-pleasing, and the radical act of not going to the damn party. In this episode, I unravel why I stopped molding myself into someone else’s ideal — whether it was for a man, a friend, or an aesthetic. I also talk about loss, what a photographer taught me about timing, and why your “no” doesn’t need an excuse (or a follow-up text). If you’ve ever contorted yourself to be chosen, approved of, or invited — this one's for you. Also, RIP to the thong I wore once in 2014.


ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth


Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1581 Stop Begging to Be Chosen And Go Where You’re Wanted This week, I’m talking about what it feels like to be unwanted—by men, by friendships, by jobs, by the popular girls with the trendy names who never wanted to sit with you at lunch. I share what growing up as the daughter of Chinese immigrants taught me about invisibility, advocacy, and watching my mom try to return a pot to Kmart in broken English while I stood there, 7 years old, already learning what it means to feel small. I talk about how I’ve slowly learned that just because someone doesn’t want you doesn’t mean you’re unworthy. It might just mean they’re not the right person, not the right door, not the right moment. I also get into rat metaphors, George Eliot, and why sometimes the bravest thing you can do is stop running and let what’s meant for you catch up. If you’ve ever felt like you had to shrink to be chosen—this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices Wed, 25 Jun 2025 17:03:00 -0000 full Anna Kai This week, I’m talking about what it feels like to be unwanted—by men, by friendships, by jobs, by the popular girls with the trendy names who never wanted to sit with you at lunch. I share what growing up as the daughter of Chinese immigrants taught me about invisibility, advocacy, and watching my mom try to return a pot to Kmart in broken English while I stood there, 7 years old, already learning what it means to feel small. I talk about how I’ve slowly learned that just because someone doesn’t want you doesn’t mean you’re unworthy. It might just mean they’re not the right person, not the right door, not the right moment. I also get into rat metaphors, George Eliot, and why sometimes the bravest thing you can do is stop running and let what’s meant for you catch up. If you’ve ever felt like you had to shrink to be chosen—this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I’m talking about what it feels like to be unwanted—by men, by friendships, by jobs, by the popular girls with the trendy names who never wanted to sit with you at lunch. I share what growing up as the daughter of Chinese immigrants taught me about invisibility, advocacy, and watching my mom try to return a pot to Kmart in broken English while I stood there, 7 years old, already learning what it means to feel small.

I talk about how I’ve slowly learned that just because someone doesn’t want you doesn’t mean you’re unworthy. It might just mean they’re not the right person, not the right door, not the right moment. I also get into rat metaphors, George Eliot, and why sometimes the bravest thing you can do is stop running and let what’s meant for you catch up.

If you’ve ever felt like you had to shrink to be chosen—this one’s for you.

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]]> 2073 My Best Friend Paid For Her Own Engagement Ring She’s 32, never had a boyfriend, and just dropped thousands to fund her own proposal — hotel, flowers, the ring he gave her. Meanwhile, he’s out here liking thirst traps and asking her for money for designer watches. In this episode, I unpack the heartbreak of watching someone you love choose delusion over dignity — and why trying to save them might actually be a way of avoiding your own sh*t. Also in this episode: • The difference between generosity and desperation (and how thin the line can be) • The ex-boyfriend I tried to impress with an espresso machine I couldn’t afford • Why today — some random Tuesday in June — might be your new beginning • The illusion of arrival — what happens after you get the life you begged for This is Brutally Anna 2.0 — where it's us just now, and nothing's off limits. Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 19 Jun 2025 18:28:00 -0000 full Anna Kai She’s 32, never had a boyfriend, and just dropped thousands to fund her own proposal — hotel, flowers, the ring he gave her. Meanwhile, he’s out here liking thirst traps and asking her for money for designer watches. In this episode, I unpack the heartbreak of watching someone you love choose delusion over dignity — and why trying to save them might actually be a way of avoiding your own sh*t. Also in this episode: • The difference between generosity and desperation (and how thin the line can be) • The ex-boyfriend I tried to impress with an espresso machine I couldn’t afford • Why today — some random Tuesday in June — might be your new beginning • The illusion of arrival — what happens after you get the life you begged for This is Brutally Anna 2.0 — where it's us just now, and nothing's off limits. Learn more about your ad choices. Visit podcastchoices.com/adchoices She’s 32, never had a boyfriend, and just dropped thousands to fund her own proposal — hotel, flowers, the ring he gave her. Meanwhile, he’s out here liking thirst traps and asking her for money for designer watches. In this episode, I unpack the heartbreak of watching someone you love choose delusion over dignity — and why trying to save them might actually be a way of avoiding your own sh*t. Also in this episode: • The difference between generosity and desperation (and how thin the line can be) • The ex-boyfriend I tried to impress with an espresso machine I couldn’t afford • Why today — some random Tuesday in June — might be your new beginning • The illusion of arrival — what happens after you get the life you begged for This is Brutally Anna 2.0 — where it's us just now, and nothing's off limits.

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]]> 1520 Never Take Life Too Seriously feat. Nicole Pellegrino On this week's episode, former director of Betches Media turned content creator Nicole Pellegrino shares her journey as we delve into her candid and often humorous takes on marriage, millennial life, and her rescue doLouie. She opens up about the impact of her mom's passing, her parents' divorce, and why she strives never to take life too seriously, because, in her words, "we're all just floating on this rock." Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Nicole: https://www.instagram.com/nicolepellegrin0 https://www.tiktok.com/@nicolepellegrin0 Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 19 May 2025 19:16:00 -0000 full Anna Kai On this week's episode, former director of Betches Media turned content creator Nicole Pellegrino shares her journey as we delve into her candid and often humorous takes on marriage, millennial life, and her rescue doLouie. She opens up about the impact of her mom's passing, her parents' divorce, and why she strives never to take life too seriously, because, in her words, "we're all just floating on this rock." Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Nicole: https://www.instagram.com/nicolepellegrin0 https://www.tiktok.com/@nicolepellegrin0 Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's episode, former director of Betches Media turned content creator Nicole Pellegrino shares her journey as we delve into her candid and often humorous takes on marriage, millennial life, and her rescue doLouie. She opens up about the impact of her mom's passing, her parents' divorce, and why she strives never to take life too seriously, because, in her words, "we're all just floating on this rock."


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Nicole:

https://www.instagram.com/nicolepellegrin0

https://www.tiktok.com/@nicolepellegrin0



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]]> 4702 Kristina Zias Isn't Afraid To Ask For Help Fashion and beauty influencer, Kristina Zias, dives into her 13-year journey from being called 'cringe' to becoming a body positivity queen featured on The Drew Barrymore Show and People Magazine. We discuss juggling motherhood, cross-country move, and running her own business and why her delusional confidence has led her to achieving (and running!) races and experiences she never thought she once could. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kristina https://www.instagram.com/kristinazias/ https://www.tiktok.com/@kristinazias Learn more about your ad choices. Visit podcastchoices.com/adchoices Tue, 13 May 2025 01:14:00 -0000 full Anna Kai Fashion and beauty influencer, Kristina Zias, dives into her 13-year journey from being called 'cringe' to becoming a body positivity queen featured on The Drew Barrymore Show and People Magazine. We discuss juggling motherhood, cross-country move, and running her own business and why her delusional confidence has led her to achieving (and running!) races and experiences she never thought she once could. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kristina https://www.instagram.com/kristinazias/ https://www.tiktok.com/@kristinazias Learn more about your ad choices. Visit podcastchoices.com/adchoices Fashion and beauty influencer, Kristina Zias, dives into her 13-year journey from being called 'cringe' to becoming a body positivity queen featured on The Drew Barrymore Show and People Magazine. We discuss juggling motherhood, cross-country move, and running her own business and why her delusional confidence has led her to achieving (and running!) races and experiences she never thought she once could.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Kristina

https://www.instagram.com/kristinazias/

https://www.tiktok.com/@kristinazias

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]]> 4693 Find The Club That Wants You feat. Zarna Garg This week, I'm joined by comedy powerhouse Zarna Garg as she recounts her transition from practicing law (where her clients mostly ended up in jail) to becoming one of Variety’s '10 Comics to Watch.' Known for her razor-sharp wit, cultural insights, and brutally honest takes on life as an immigrant mom, Zarna dishes on her zig-zag journey. Imagine litigating to realizing you’re better at telling jokes about your mother-in-law than getting people out of jail. Add 16 years as a stay-at-home mom in NYC (three kids and a soul-crushing shoe-box apartment), and you have the perfect recipe for a comedy. Listen as Zarna talks about her stumble into a comedy club, where she hilariously tore into her mother-in-law and had an epiphany: 'Hey, I’m good at this!' She also doles out practical advice: dreams can change (now she’s got someone else getting her cilantro), persistence beats proof, and even gives a shout-out to her 'world-class ego destroyer' mother-in-law. Zarna's story is as inspiring as it is hilarious, packed with eye-openers on motherhood, chasing dreams, and making audiences—and mother-in-laws—laugh out loud. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Zarna https://www.instagram.com/zarnagarg/ https://www.tiktok.com/@zarnagarg Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 05 May 2025 19:44:00 -0000 full Anna Kai This week, I'm joined by comedy powerhouse Zarna Garg as she recounts her transition from practicing law (where her clients mostly ended up in jail) to becoming one of Variety’s '10 Comics to Watch.' Known for her razor-sharp wit, cultural insights, and brutally honest takes on life as an immigrant mom, Zarna dishes on her zig-zag journey. Imagine litigating to realizing you’re better at telling jokes about your mother-in-law than getting people out of jail. Add 16 years as a stay-at-home mom in NYC (three kids and a soul-crushing shoe-box apartment), and you have the perfect recipe for a comedy. Listen as Zarna talks about her stumble into a comedy club, where she hilariously tore into her mother-in-law and had an epiphany: 'Hey, I’m good at this!' She also doles out practical advice: dreams can change (now she’s got someone else getting her cilantro), persistence beats proof, and even gives a shout-out to her 'world-class ego destroyer' mother-in-law. Zarna's story is as inspiring as it is hilarious, packed with eye-openers on motherhood, chasing dreams, and making audiences—and mother-in-laws—laugh out loud. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Zarna https://www.instagram.com/zarnagarg/ https://www.tiktok.com/@zarnagarg Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I'm joined by comedy powerhouse Zarna Garg as she recounts her transition from practicing law (where her clients mostly ended up in jail) to becoming one of Variety’s '10 Comics to Watch.' Known for her razor-sharp wit, cultural insights, and brutally honest takes on life as an immigrant mom, Zarna dishes on her zig-zag journey. Imagine litigating to realizing you’re better at telling jokes about your mother-in-law than getting people out of jail. Add 16 years as a stay-at-home mom in NYC (three kids and a soul-crushing shoe-box apartment), and you have the perfect recipe for a comedy. Listen as Zarna talks about her stumble into a comedy club, where she hilariously tore into her mother-in-law and had an epiphany: 'Hey, I’m good at this!' She also doles out practical advice: dreams can change (now she’s got someone else getting her cilantro), persistence beats proof, and even gives a shout-out to her 'world-class ego destroyer' mother-in-law. Zarna's story is as inspiring as it is hilarious, packed with eye-openers on motherhood, chasing dreams, and making audiences—and mother-in-laws—laugh out loud.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Zarna

https://www.instagram.com/zarnagarg/

https://www.tiktok.com/@zarnagarg

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]]> 3453 You're Not Crazy, You Just Need To Sleep Feat. Bran Flakezz From his humble beginnings playing with Barbies, dealing with bullies, and rocking TJ Maxx instead of Abercrombie, Bran shares how he went from the "fat, poor, gay kid" to our internet gay bestie. Bran recounts his first Grindr hookup (complete with crabs) and dishes on his modern-day love life: think more situational-ships than relationships. We get real about his epic mental health breakdown, panic disorders, and how therapy and meds turned things around. Now, he's all about self-love, spreading good vibes, and focusing on making bank before worrying about love. My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Bran: https://www.instagram.com/bran_flakezz https://www.tiktok.com/@bran_flakezz Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 28 Apr 2025 17:48:00 -0000 full Anna Kai From his humble beginnings playing with Barbies, dealing with bullies, and rocking TJ Maxx instead of Abercrombie, Bran shares how he went from the "fat, poor, gay kid" to our internet gay bestie. Bran recounts his first Grindr hookup (complete with crabs) and dishes on his modern-day love life: think more situational-ships than relationships. We get real about his epic mental health breakdown, panic disorders, and how therapy and meds turned things around. Now, he's all about self-love, spreading good vibes, and focusing on making bank before worrying about love. My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Bran: https://www.instagram.com/bran_flakezz https://www.tiktok.com/@bran_flakezz Learn more about your ad choices. Visit podcastchoices.com/adchoices From his humble beginnings playing with Barbies, dealing with bullies, and rocking TJ Maxx instead of Abercrombie, Bran shares how he went from the "fat, poor, gay kid" to our internet gay bestie. Bran recounts his first Grindr hookup (complete with crabs) and dishes on his modern-day love life: think more situational-ships than relationships. We get real about his epic mental health breakdown, panic disorders, and how therapy and meds turned things around. Now, he's all about self-love, spreading good vibes, and focusing on making bank before worrying about love.


My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Bran:

https://www.instagram.com/bran_flakezz

https://www.tiktok.com/@bran_flakezz

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]]> 3204 Behind the Whimsy: Noelle Downing on Overcoming Tragedy and Embracing Life My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Noelle: https://www.instagram.com/noelledowning/ https://www.tiktok.com/@noelledowning Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 21 Apr 2025 09:00:00 -0000 full Anna Kai My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Noelle: https://www.instagram.com/noelledowning/ https://www.tiktok.com/@noelledowning Learn more about your ad choices. Visit podcastchoices.com/adchoices My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Noelle:

https://www.instagram.com/noelledowning/

https://www.tiktok.com/@noelledowning

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3286 Let Yourself Suck At It First feat. Anna Akana Comedian, social media sensation, and bestselling author Anna Akana joins me this week as she discusses her journey from dealing with the tragic loss of her sister to suicide to becoming a comedian where she found solace in making others laugh. We dive deep into the challenges of dating in LA, dealing with grief, the quirks of menstrual products, and the importance of allowing yourself to be bad at something before you get good. Plus, you'll laugh at some truly unexpected places, like when we discuss leaving a menstrual disc in for three months (yes, really). It's about turning your pain into your power and remembering to enjoy the process—even when life’s a bit of a mess. Follow Anna Kai: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Anna Akana: https://www.instagram.com/annaakana https://www.youtube.com/user/AnnaAkana https://www.tiktok.com/@annaakana Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 14 Apr 2025 09:00:00 -0000 full Anna Kai Comedian, social media sensation, and bestselling author Anna Akana joins me this week as she discusses her journey from dealing with the tragic loss of her sister to suicide to becoming a comedian where she found solace in making others laugh. We dive deep into the challenges of dating in LA, dealing with grief, the quirks of menstrual products, and the importance of allowing yourself to be bad at something before you get good. Plus, you'll laugh at some truly unexpected places, like when we discuss leaving a menstrual disc in for three months (yes, really). It's about turning your pain into your power and remembering to enjoy the process—even when life’s a bit of a mess. Follow Anna Kai: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Anna Akana: https://www.instagram.com/annaakana https://www.youtube.com/user/AnnaAkana https://www.tiktok.com/@annaakana Learn more about your ad choices. Visit podcastchoices.com/adchoices Comedian, social media sensation, and bestselling author Anna Akana joins me this week as she discusses her journey from dealing with the tragic loss of her sister to suicide to becoming a comedian where she found solace in making others laugh. We dive deep into the challenges of dating in LA, dealing with grief, the quirks of menstrual products, and the importance of allowing yourself to be bad at something before you get good. Plus, you'll laugh at some truly unexpected places, like when we discuss leaving a menstrual disc in for three months (yes, really). It's about turning your pain into your power and remembering to enjoy the process—even when life’s a bit of a mess.


Follow Anna Kai:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Anna Akana:

https://www.instagram.com/annaakana

https://www.youtube.com/user/AnnaAkana

https://www.tiktok.com/@annaakana

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]]> 2716 Raven Ross On How An Eating Disorder Led To Her Pilates Career Creator of Pilates Body Hotties and former Love Is Blind cast member Raven Ross joins me this week to talk about her transformative journey from a self-described shitshow to the wellness maven she is today. Raven reflects on life in her early twenties working three jobs, the impulsive decision to join 'Love is Blind,' and navigating public scrutiny while staying true to herself. She delves into her early passion for pilates, her struggles with body image and eating disorders from her dance career, and the profound impact of losing her father suddenly last year. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Raven: https://www.instagram.com/pilatesbodyraven https://www.youtube.com/@pilatesbodyraven https://www.tiktok.com/@pilatesbodyraven Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 07 Apr 2025 09:00:00 -0000 full Anna Kai Creator of Pilates Body Hotties and former Love Is Blind cast member Raven Ross joins me this week to talk about her transformative journey from a self-described shitshow to the wellness maven she is today. Raven reflects on life in her early twenties working three jobs, the impulsive decision to join 'Love is Blind,' and navigating public scrutiny while staying true to herself. She delves into her early passion for pilates, her struggles with body image and eating disorders from her dance career, and the profound impact of losing her father suddenly last year. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Raven: https://www.instagram.com/pilatesbodyraven https://www.youtube.com/@pilatesbodyraven https://www.tiktok.com/@pilatesbodyraven Learn more about your ad choices. Visit podcastchoices.com/adchoices Creator of Pilates Body Hotties and former Love Is Blind cast member Raven Ross joins me this week to talk about her transformative journey from a self-described shitshow to the wellness maven she is today. Raven reflects on life in her early twenties working three jobs, the impulsive decision to join 'Love is Blind,' and navigating public scrutiny while staying true to herself. She delves into her early passion for pilates, her struggles with body image and eating disorders from her dance career, and the profound impact of losing her father suddenly last year.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Raven:

https://www.instagram.com/pilatesbodyraven

https://www.youtube.com/@pilatesbodyraven

https://www.tiktok.com/@pilatesbodyraven

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2505 Solo Episode: Every Door Closing Means Another One Opening Picture this: I'm chilling (or warming really) in a swanky Utah hotel room, staring at a scenic snowy mountain while my outdoor gas fireplace blazes away because I couldn't figure out how to turn it off. I'm here on a brand trip, but before this, I was in LA for a memorial. Some heavy stuff has been on my mind: the sudden loss of loved ones, the meaning of life, and what's truly important. Spoiler: It's not meeting work deadlines. I'm also grappling with our existence, the supernatural, and what's out there after our brains clock out. There's even a spooky story about a kid seeing a deceased 'Uncle Jack'. Major existential vibes. Oh, and plot twist: this will be my last solo podcast episode for a bit. I'm launching a fantastic newsletter called Brutal Banter, so find me there for all the inspo and skincare deets. Exciting stuff, right? Catch you on the flip side! Subscribe to my free weekly newsletter: https://brutalbanter.beehiiv.com/ Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 03 Apr 2025 09:00:00 -0000 full Anna Kai Picture this: I'm chilling (or warming really) in a swanky Utah hotel room, staring at a scenic snowy mountain while my outdoor gas fireplace blazes away because I couldn't figure out how to turn it off. I'm here on a brand trip, but before this, I was in LA for a memorial. Some heavy stuff has been on my mind: the sudden loss of loved ones, the meaning of life, and what's truly important. Spoiler: It's not meeting work deadlines. I'm also grappling with our existence, the supernatural, and what's out there after our brains clock out. There's even a spooky story about a kid seeing a deceased 'Uncle Jack'. Major existential vibes. Oh, and plot twist: this will be my last solo podcast episode for a bit. I'm launching a fantastic newsletter called Brutal Banter, so find me there for all the inspo and skincare deets. Exciting stuff, right? Catch you on the flip side! Subscribe to my free weekly newsletter: https://brutalbanter.beehiiv.com/ Learn more about your ad choices. Visit podcastchoices.com/adchoices Picture this: I'm chilling (or warming really) in a swanky Utah hotel room, staring at a scenic snowy mountain while my outdoor gas fireplace blazes away because I couldn't figure out how to turn it off. I'm here on a brand trip, but before this, I was in LA for a memorial. Some heavy stuff has been on my mind: the sudden loss of loved ones, the meaning of life, and what's truly important. Spoiler: It's not meeting work deadlines. I'm also grappling with our existence, the supernatural, and what's out there after our brains clock out. There's even a spooky story about a kid seeing a deceased 'Uncle Jack'. Major existential vibes. Oh, and plot twist: this will be my last solo podcast episode for a bit. I'm launching a fantastic newsletter called Brutal Banter, so find me there for all the inspo and skincare deets. Exciting stuff, right? Catch you on the flip side!


Subscribe to my free weekly newsletter: https://brutalbanter.beehiiv.com/


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]]> 1400 Jenny Yang Is Captain Save A Ho Jenny Yang has tried to save the world in many ways, but for now, she's saving us all with a little bit of humor. Named as one of Variety's top 10 comics to watch. Jenny talks about her transition from her slam poetry days and a high-stress career in politics to comedy. She shares how her upbringing as an Asian American immigrant shaped her path and her passion for representation in Hollywood. Jenny opens up about personal struggles during the pandemic, including the loss of her father and coping with mental health. We also dive into her love story with her fiancé, how they met on a dating app during the pandemic, and what he said to her after she mixed up her dad's grave with a stranger's. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Jenny: https://www.instagram.com/jennyyangtv https://jennyyang.substack.com/ Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 31 Mar 2025 09:00:00 -0000 full Anna Kai Jenny Yang has tried to save the world in many ways, but for now, she's saving us all with a little bit of humor. Named as one of Variety's top 10 comics to watch. Jenny talks about her transition from her slam poetry days and a high-stress career in politics to comedy. She shares how her upbringing as an Asian American immigrant shaped her path and her passion for representation in Hollywood. Jenny opens up about personal struggles during the pandemic, including the loss of her father and coping with mental health. We also dive into her love story with her fiancé, how they met on a dating app during the pandemic, and what he said to her after she mixed up her dad's grave with a stranger's. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Jenny: https://www.instagram.com/jennyyangtv https://jennyyang.substack.com/ Learn more about your ad choices. Visit podcastchoices.com/adchoices Jenny Yang has tried to save the world in many ways, but for now, she's saving us all with a little bit of humor. Named as one of Variety's top 10 comics to watch. Jenny talks about her transition from her slam poetry days and a high-stress career in politics to comedy. She shares how her upbringing as an Asian American immigrant shaped her path and her passion for representation in Hollywood. Jenny opens up about personal struggles during the pandemic, including the loss of her father and coping with mental health. We also dive into her love story with her fiancé, how they met on a dating app during the pandemic, and what he said to her after she mixed up her dad's grave with a stranger's.


Follow Anna:

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https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Jenny:

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https://jennyyang.substack.com/

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]]> 4267 Solo Episode: Girl Scout Cookies Trigger Me I'm scared of K-12 kids, having kids, and having kids who might get bullied. Unpacking all of the above on this week's solo episode after an encounter with Girl Scouts selling cookies and why I think I'd be capable of murder (under the right circumstances! It's a joke - don't come after me FBI!). I tackle listener voicemails about toxic friendships (not all friends are forever) and family dramas. Stick around for my reflections on death and celebrating life, and why flying back to LA for a family event made me rethink the grind. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 27 Mar 2025 09:00:00 -0000 full Anna Kai I'm scared of K-12 kids, having kids, and having kids who might get bullied. Unpacking all of the above on this week's solo episode after an encounter with Girl Scouts selling cookies and why I think I'd be capable of murder (under the right circumstances! It's a joke - don't come after me FBI!). I tackle listener voicemails about toxic friendships (not all friends are forever) and family dramas. Stick around for my reflections on death and celebrating life, and why flying back to LA for a family event made me rethink the grind. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices I'm scared of K-12 kids, having kids, and having kids who might get bullied. Unpacking all of the above on this week's solo episode after an encounter with Girl Scouts selling cookies and why I think I'd be capable of murder (under the right circumstances! It's a joke - don't come after me FBI!). I tackle listener voicemails about toxic friendships (not all friends are forever) and family dramas. Stick around for my reflections on death and celebrating life, and why flying back to LA for a family event made me rethink the grind.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

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]]> 2843 The Language of Grief feat. Ashley LeMieux On this week's episode, podcaster and wellness coach Ashley Lemieux opens up about the heartbreaking loss of her unborn son to sepsis in 2020 and how she turned her grief into a mission to help others. Ashley talks about her hit podcast 'Healing Her,' her social media channels, and her bestselling books, all aimed at supporting people navigating some of the most heartbreaking moments of their lives. She also shares personal stories about her faith journey, body positivity, and how her relationship with her husband changed as they navigated losing a child together. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Ashley https://www.instagram.com/ashleyklemieux Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 24 Mar 2025 09:00:00 -0000 full Anna Kai On this week's episode, podcaster and wellness coach Ashley Lemieux opens up about the heartbreaking loss of her unborn son to sepsis in 2020 and how she turned her grief into a mission to help others. Ashley talks about her hit podcast 'Healing Her,' her social media channels, and her bestselling books, all aimed at supporting people navigating some of the most heartbreaking moments of their lives. She also shares personal stories about her faith journey, body positivity, and how her relationship with her husband changed as they navigated losing a child together. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Ashley https://www.instagram.com/ashleyklemieux Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's episode, podcaster and wellness coach Ashley Lemieux opens up about the heartbreaking loss of her unborn son to sepsis in 2020 and how she turned her grief into a mission to help others. Ashley talks about her hit podcast 'Healing Her,' her social media channels, and her bestselling books, all aimed at supporting people navigating some of the most heartbreaking moments of their lives. She also shares personal stories about her faith journey, body positivity, and how her relationship with her husband changed as they navigated losing a child together.


Follow Anna:

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https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Ashley

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]]> 5135 Solo Episode: The Privilege of Trying We're talking DIY pest control, why owning a home is (kind of) a scam (that I willingly participate in and have a love/hate relationship with), and why it's a privilege to be able to try at all, even if you fail. I discuss why we need to make it more socially acceptable for women not to be motivated by some higher "purpose" other than making a living, and I answer a listener's question about what to do when you're tired of dating and don't feel like you're making any progress. Lastly, I rant about getting enough sleep, because it's not a badge of honor to deprive yourself of what your body needs. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 20 Mar 2025 09:00:00 -0000 full Anna Kai We're talking DIY pest control, why owning a home is (kind of) a scam (that I willingly participate in and have a love/hate relationship with), and why it's a privilege to be able to try at all, even if you fail. I discuss why we need to make it more socially acceptable for women not to be motivated by some higher "purpose" other than making a living, and I answer a listener's question about what to do when you're tired of dating and don't feel like you're making any progress. Lastly, I rant about getting enough sleep, because it's not a badge of honor to deprive yourself of what your body needs. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices We're talking DIY pest control, why owning a home is (kind of) a scam (that I willingly participate in and have a love/hate relationship with), and why it's a privilege to be able to try at all, even if you fail. I discuss why we need to make it more socially acceptable for women not to be motivated by some higher "purpose" other than making a living, and I answer a listener's question about what to do when you're tired of dating and don't feel like you're making any progress. Lastly, I rant about getting enough sleep, because it's not a badge of honor to deprive yourself of what your body needs.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


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]]> 1809 Finding Love In A Club In Mexico feat. Lindsay Silberman This week, I'm joined by founder and self-proclaimed candle snob, Lindsay Silberman. From her ambitious beginnings as a magazine editor to pivoting into the world of social media influencing and entrepreneurship. Lindsay reflects on her career in the evolving magazine industry and how being hit by a car in 2018 gave her a new lease on life. She takes us through the highs and lows of launching her candle brand, Hotel Lobby Candle, during the pandemic and how she met her husband and business partner in one of the most unexpected places. We dive into her decision not to become a mother (at least for now), freezing embryos, and why these days, Lindsay is more focused on building a business than she is building a family. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Lindsay https://www.instagram.com/lindsaysilb https://www.tiktok.com/@lindsaysilb Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 17 Mar 2025 09:00:00 -0000 full Anna Kai This week, I'm joined by founder and self-proclaimed candle snob, Lindsay Silberman. From her ambitious beginnings as a magazine editor to pivoting into the world of social media influencing and entrepreneurship. Lindsay reflects on her career in the evolving magazine industry and how being hit by a car in 2018 gave her a new lease on life. She takes us through the highs and lows of launching her candle brand, Hotel Lobby Candle, during the pandemic and how she met her husband and business partner in one of the most unexpected places. We dive into her decision not to become a mother (at least for now), freezing embryos, and why these days, Lindsay is more focused on building a business than she is building a family. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Lindsay https://www.instagram.com/lindsaysilb https://www.tiktok.com/@lindsaysilb Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I'm joined by founder and self-proclaimed candle snob, Lindsay Silberman. From her ambitious beginnings as a magazine editor to pivoting into the world of social media influencing and entrepreneurship. Lindsay reflects on her career in the evolving magazine industry and how being hit by a car in 2018 gave her a new lease on life. She takes us through the highs and lows of launching her candle brand, Hotel Lobby Candle, during the pandemic and how she met her husband and business partner in one of the most unexpected places. We dive into her decision not to become a mother (at least for now), freezing embryos, and why these days, Lindsay is more focused on building a business than she is building a family.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Lindsay

https://www.instagram.com/lindsaysilb

https://www.tiktok.com/@lindsaysilb

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]]> 4766 Solo Episode: It's Never As Bad As It Seems And Why Your Dreams Need To Change On this week's solo episode, I'd like to remind that you that for every time I thought my life was ending in my twenties, it didn't. And so, if my dramatic ass can recover from every breakup, career failure, and cringeworthy moment I've lived through, so can you. I welcome you into the chaos of my inner world because even your queen biddie can get caught up in what's next versus what is now. I read some juicy secrets from you guys on this week's IG stories (a 51-year-old educator turned luxury escort, anyone?) and tackle your dilemmas—like moving away from family and why becoming a 'failed' singer-songwriter was the best thing that ever happened to me and why maybe your dreams don't have to die, they just need to change. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 13 Mar 2025 09:00:00 -0000 full Anna Kai On this week's solo episode, I'd like to remind that you that for every time I thought my life was ending in my twenties, it didn't. And so, if my dramatic ass can recover from every breakup, career failure, and cringeworthy moment I've lived through, so can you. I welcome you into the chaos of my inner world because even your queen biddie can get caught up in what's next versus what is now. I read some juicy secrets from you guys on this week's IG stories (a 51-year-old educator turned luxury escort, anyone?) and tackle your dilemmas—like moving away from family and why becoming a 'failed' singer-songwriter was the best thing that ever happened to me and why maybe your dreams don't have to die, they just need to change. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's solo episode, I'd like to remind that you that for every time I thought my life was ending in my twenties, it didn't. And so, if my dramatic ass can recover from every breakup, career failure, and cringeworthy moment I've lived through, so can you. I welcome you into the chaos of my inner world because even your queen biddie can get caught up in what's next versus what is now. I read some juicy secrets from you guys on this week's IG stories (a 51-year-old educator turned luxury escort, anyone?) and tackle your dilemmas—like moving away from family and why becoming a 'failed' singer-songwriter was the best thing that ever happened to me and why maybe your dreams don't have to die, they just need to change.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

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]]> 2342 Navigating Life's Unwritten Chapters feat. Loren Ridinger On this week's episode, we dive into the life of powerhouse entrepreneur and NYT bestselling author, Loren Ridinger, who shares her story of building a global business empire with Market America and Shop.com alongside her late husband, JR. The conversation explores 'Life After Rejection,' as Lauren recounts their early years, falling for JR despite his initial disinterest, and their shared vision that transformed into a legacy. Lauren recounts meeting JR at the age of 18, the challenges they faced, how JR's vision of an online shopping future defied skeptics, and how he instilled confidence in her to speak publicly despite her fears. She provides a raw and heartfelt account of the grief process, describing the early days of loss as a foggy and dark period, and also discussing the spiritual signs that have helped her feel JR’s presence after his passing. Her memoir, 'Scrambled or Sunny Side Up,' details her journey of rediscovery following the sudden and immense loss of JR. Lauren discusses finding strength, navigating grief, and ultimately reinventing herself, offering relatable advice on dating yourself and learning to love yourself first in the face of societal expectations. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Loren: https://www.instagram.com/lorenridinger Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 10 Mar 2025 05:00:00 -0000 full Anna Kai On this week's episode, we dive into the life of powerhouse entrepreneur and NYT bestselling author, Loren Ridinger, who shares her story of building a global business empire with Market America and Shop.com alongside her late husband, JR. The conversation explores 'Life After Rejection,' as Lauren recounts their early years, falling for JR despite his initial disinterest, and their shared vision that transformed into a legacy. Lauren recounts meeting JR at the age of 18, the challenges they faced, how JR's vision of an online shopping future defied skeptics, and how he instilled confidence in her to speak publicly despite her fears. She provides a raw and heartfelt account of the grief process, describing the early days of loss as a foggy and dark period, and also discussing the spiritual signs that have helped her feel JR’s presence after his passing. Her memoir, 'Scrambled or Sunny Side Up,' details her journey of rediscovery following the sudden and immense loss of JR. Lauren discusses finding strength, navigating grief, and ultimately reinventing herself, offering relatable advice on dating yourself and learning to love yourself first in the face of societal expectations. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Loren: https://www.instagram.com/lorenridinger Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's episode, we dive into the life of powerhouse entrepreneur and NYT bestselling author, Loren Ridinger, who shares her story of building a global business empire with Market America and Shop.com alongside her late husband, JR. The conversation explores 'Life After Rejection,' as Lauren recounts their early years, falling for JR despite his initial disinterest, and their shared vision that transformed into a legacy.


Lauren recounts meeting JR at the age of 18, the challenges they faced, how JR's vision of an online shopping future defied skeptics, and how he instilled confidence in her to speak publicly despite her fears. She provides a raw and heartfelt account of the grief process, describing the early days of loss as a foggy and dark period, and also discussing the spiritual signs that have helped her feel JR’s presence after his passing.


Her memoir, 'Scrambled or Sunny Side Up,' details her journey of rediscovery following the sudden and immense loss of JR. Lauren discusses finding strength, navigating grief, and ultimately reinventing herself, offering relatable advice on dating yourself and learning to love yourself first in the face of societal expectations.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Loren:

https://www.instagram.com/lorenridinger

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2607 Solo Episode: Breaking Up With Friends and the Power of Your Solitude It turns out I didn't need a higher dosage of my Zoloft, I just needed eight hours of sleep. Speaking to you from Florida, I'm sharing all my thoughts this week on prioritizing yourself and why taking a step back can sometimes be the only way forward. We're taking a deep dive into the awkward realm of friendship breakups, why it's important to know the difference between someone who wants to be friends with you and someone who wants to be friends with you in order to use you, and why learning to enjoy your own company is the only way to keep yourself from staying in toxic friendships. I'm answering voicemails from a biddie torn between staying in Italy with her super supportive, boyfriend or taking her dream job in Sydney. Hint: I might have told her to 'choose herself', but you'll have to listen to find out. I also discuss why you should find a partner who loves the current you—not some 'improved version' of you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 06 Mar 2025 10:00:00 -0000 full Anna Kai It turns out I didn't need a higher dosage of my Zoloft, I just needed eight hours of sleep. Speaking to you from Florida, I'm sharing all my thoughts this week on prioritizing yourself and why taking a step back can sometimes be the only way forward. We're taking a deep dive into the awkward realm of friendship breakups, why it's important to know the difference between someone who wants to be friends with you and someone who wants to be friends with you in order to use you, and why learning to enjoy your own company is the only way to keep yourself from staying in toxic friendships. I'm answering voicemails from a biddie torn between staying in Italy with her super supportive, boyfriend or taking her dream job in Sydney. Hint: I might have told her to 'choose herself', but you'll have to listen to find out. I also discuss why you should find a partner who loves the current you—not some 'improved version' of you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices It turns out I didn't need a higher dosage of my Zoloft, I just needed eight hours of sleep. Speaking to you from Florida, I'm sharing all my thoughts this week on prioritizing yourself and why taking a step back can sometimes be the only way forward. We're taking a deep dive into the awkward realm of friendship breakups, why it's important to know the difference between someone who wants to be friends with you and someone who wants to be friends with you in order to use you, and why learning to enjoy your own company is the only way to keep yourself from staying in toxic friendships.

I'm answering voicemails from a biddie torn between staying in Italy with her super supportive, boyfriend or taking her dream job in Sydney. Hint: I might have told her to 'choose herself', but you'll have to listen to find out. I also discuss why you should find a partner who loves the current you—not some 'improved version' of you.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2958 Radhi Devlukia's Recipe for a Delicious Love Life This week, I sit down with Radhi Devlukia, a New York Times bestselling author, wellness influencer, and entrepreneur, about her journey from being a dietitian to becoming a holistic wellness advocate. Radhi delves into her upbringing in the UK, her career transition from aspiring pediatrician to dietitian following her mother’s advice, and her subsequent interest in Ayurveda. She highlights the importance of making small, sustainable changes for better health, discussing practices like breathwork, meditation, and dietary modifications. Radhi also opens up about struggling with emotional eating and how she overcame her sugar addiction. We get a peak into how she navigated the early days of her relationship with her husband, Jay Shetty, marked by Jay’s transition from monkhood and their subsequent move to New York for his career. Despite the challenges, Radhi emphasizes the importance of personal identity and shared spiritual growth in their partnership. She candidly discusses the complexities of maintaining her unique identity while being associated with a well-known spouse and stresses her preference for being known by her maiden name, Radhi Devlukia. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Radhi: https://www.instagram.com/radhidevlukia/?hl=en https://www.tiktok.com/@radhidevlukia?lang=en https://www.youtube.com/channel/UCxWe9A4kMf9V_AHOXkGhCzQ Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 03 Mar 2025 10:00:00 -0000 full Anna Kai This week, I sit down with Radhi Devlukia, a New York Times bestselling author, wellness influencer, and entrepreneur, about her journey from being a dietitian to becoming a holistic wellness advocate. Radhi delves into her upbringing in the UK, her career transition from aspiring pediatrician to dietitian following her mother’s advice, and her subsequent interest in Ayurveda. She highlights the importance of making small, sustainable changes for better health, discussing practices like breathwork, meditation, and dietary modifications. Radhi also opens up about struggling with emotional eating and how she overcame her sugar addiction. We get a peak into how she navigated the early days of her relationship with her husband, Jay Shetty, marked by Jay’s transition from monkhood and their subsequent move to New York for his career. Despite the challenges, Radhi emphasizes the importance of personal identity and shared spiritual growth in their partnership. She candidly discusses the complexities of maintaining her unique identity while being associated with a well-known spouse and stresses her preference for being known by her maiden name, Radhi Devlukia. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Radhi: https://www.instagram.com/radhidevlukia/?hl=en https://www.tiktok.com/@radhidevlukia?lang=en https://www.youtube.com/channel/UCxWe9A4kMf9V_AHOXkGhCzQ Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I sit down with Radhi Devlukia, a New York Times bestselling author, wellness influencer, and entrepreneur, about her journey from being a dietitian to becoming a holistic wellness advocate. Radhi delves into her upbringing in the UK, her career transition from aspiring pediatrician to dietitian following her mother’s advice, and her subsequent interest in Ayurveda. She highlights the importance of making small, sustainable changes for better health, discussing practices like breathwork, meditation, and dietary modifications.


Radhi also opens up about struggling with emotional eating and how she overcame her sugar addiction. We get a peak into how she navigated the early days of her relationship with her husband, Jay Shetty, marked by Jay’s transition from monkhood and their subsequent move to New York for his career. Despite the challenges, Radhi emphasizes the importance of personal identity and shared spiritual growth in their partnership. She candidly discusses the complexities of maintaining her unique identity while being associated with a well-known spouse and stresses her preference for being known by her maiden name, Radhi Devlukia.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Radhi:

https://www.instagram.com/radhidevlukia/?hl=en

https://www.tiktok.com/@radhidevlukia?lang=en

https://www.youtube.com/channel/UCxWe9A4kMf9V_AHOXkGhCzQ


Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3022 Solo Episode: Weddings, Boundaries, and the Joy of Missing Out It's a mini solo this week because I not only left a coffee curdling in my closet for four days, I'm also losing my voice. We're diving into the madness of weddings this week - from extortionate bachelorette parties to bridezilla friends and how to handle those years when you feel like you're blowing all your free time and life savings on wedding-related events. I talk about the importance of setting boundaries and the liberating joy of saying 'no,' which reminds me to also, say 'no' to recording more and to get some f*cking rest. I'll be back next week with a full solo and answers to your voicemails! Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 27 Feb 2025 10:00:00 -0000 full Anna Kai It's a mini solo this week because I not only left a coffee curdling in my closet for four days, I'm also losing my voice. We're diving into the madness of weddings this week - from extortionate bachelorette parties to bridezilla friends and how to handle those years when you feel like you're blowing all your free time and life savings on wedding-related events. I talk about the importance of setting boundaries and the liberating joy of saying 'no,' which reminds me to also, say 'no' to recording more and to get some f*cking rest. I'll be back next week with a full solo and answers to your voicemails! Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices It's a mini solo this week because I not only left a coffee curdling in my closet for four days, I'm also losing my voice. We're diving into the madness of weddings this week - from extortionate bachelorette parties to bridezilla friends and how to handle those years when you feel like you're blowing all your free time and life savings on wedding-related events. I talk about the importance of setting boundaries and the liberating joy of saying 'no,' which reminds me to also, say 'no' to recording more and to get some f*cking rest. I'll be back next week with a full solo and answers to your voicemails!


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 1020 Stop Settling For a Life and Love You Don't Deserve feat. Joanne Molinaro On this week's guest episode, I'm joined by Joanne Lee Molinaro, aka The Korean Vegan, who reveals her journey from courtroom drama to cooking fame. With nearly 5 million followers, she's not just whipping up vegan delights but also running marathons, publishing NYT bestsellers and winning awards (ahem, hello James Beard). Joanne gets real about growing up as a child of North Korean immigrants in suburban Illinois, feeling like an outsider, and why she chose her first career in law. She opens up about her past marriage, sharing how she eventually 'Googled how to stop crying' and found the courage to leave an abusive relationship. Joanne discusses navigating the world of online for the first time at 35, meeting her now-husband, and how going vegan and becoming a marathon runner reshaped her life, turning food from a frenemy to a source of empowerment. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Joanne: https://www.instagram.com/thekoreanvegan/?hl=en https://www.youtube.com/@TheKoreanVegan/featured https://www.tiktok.com/@thekoreanvegan?lang=en Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 24 Feb 2025 10:00:00 -0000 full Anna Kai On this week's guest episode, I'm joined by Joanne Lee Molinaro, aka The Korean Vegan, who reveals her journey from courtroom drama to cooking fame. With nearly 5 million followers, she's not just whipping up vegan delights but also running marathons, publishing NYT bestsellers and winning awards (ahem, hello James Beard). Joanne gets real about growing up as a child of North Korean immigrants in suburban Illinois, feeling like an outsider, and why she chose her first career in law. She opens up about her past marriage, sharing how she eventually 'Googled how to stop crying' and found the courage to leave an abusive relationship. Joanne discusses navigating the world of online for the first time at 35, meeting her now-husband, and how going vegan and becoming a marathon runner reshaped her life, turning food from a frenemy to a source of empowerment. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Joanne: https://www.instagram.com/thekoreanvegan/?hl=en https://www.youtube.com/@TheKoreanVegan/featured https://www.tiktok.com/@thekoreanvegan?lang=en Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's guest episode, I'm joined by Joanne Lee Molinaro, aka The Korean Vegan, who reveals her journey from courtroom drama to cooking fame. With nearly 5 million followers, she's not just whipping up vegan delights but also running marathons, publishing NYT bestsellers and winning awards (ahem, hello James Beard). Joanne gets real about growing up as a child of North Korean immigrants in suburban Illinois, feeling like an outsider, and why she chose her first career in law.


She opens up about her past marriage, sharing how she eventually 'Googled how to stop crying' and found the courage to leave an abusive relationship. Joanne discusses navigating the world of online for the first time at 35, meeting her now-husband, and how going vegan and becoming a marathon runner reshaped her life, turning food from a frenemy to a source of empowerment.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Joanne:

https://www.instagram.com/thekoreanvegan/?hl=en

https://www.youtube.com/@TheKoreanVegan/featured

https://www.tiktok.com/@thekoreanvegan?lang=en

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3996 Solo Episode: Your Comfort Zone Is Crippling You We lost power for 40 hours in 18 degree weather! On this week's solo episode, I muse on how losing power reinforced the fact that I will never like camping and why my version of being "outdoorsy" involves a screened-in porch and a temperature controlled room nearby. We dive into why your comfort zone is killing your potential, and why you shouldn't settle for what's familiar just because the unfamiliar gives you heebie jeebies. I dive into your voicemails on whether you might be mistaking drama for romance, and why you're really not as old as you think you are. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 20 Feb 2025 10:00:00 -0000 full Anna Kai We lost power for 40 hours in 18 degree weather! On this week's solo episode, I muse on how losing power reinforced the fact that I will never like camping and why my version of being "outdoorsy" involves a screened-in porch and a temperature controlled room nearby. We dive into why your comfort zone is killing your potential, and why you shouldn't settle for what's familiar just because the unfamiliar gives you heebie jeebies. I dive into your voicemails on whether you might be mistaking drama for romance, and why you're really not as old as you think you are. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices We lost power for 40 hours in 18 degree weather! On this week's solo episode, I muse on how losing power reinforced the fact that I will never like camping and why my version of being "outdoorsy" involves a screened-in porch and a temperature controlled room nearby. We dive into why your comfort zone is killing your potential, and why you shouldn't settle for what's familiar just because the unfamiliar gives you heebie jeebies. I dive into your voicemails on whether you might be mistaking drama for romance, and why you're really not as old as you think you are.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2725 The art of taking life less seriously feat. Hayden Cohen Our favorite influencer who makes us all feel better about sh*tting on influencers, Hayden Cohen (aka @hayderz), shares his journey on this week’s episode from handling social media for brands to becoming a social media sensation himself. Since 2020, Hayden has been known for his humorous and all-too-accurate impersonations of influencers, reminding us that it pays to take life a little less seriously sometimes. Hayden discusses his early days of content creation, the chaos of his days behind-the scenes managing influencers, and his experiences with influencer culture. He also touches on his life before Instagram-fame, including his close-knit family, his experiences growing up gay, and his first (and last!) relationship with his boyfriend, Aaron. Our conversation sheds light on the balance between online personas and real life, the wild world of influencing, and the importance of remaining grounded despite newfound internet fame. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Hayden: @hayderz Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 17 Feb 2025 10:00:00 -0000 The art of taking life less seriously feat. Hayden Cohen full Anna Kai Our favorite influencer who makes us all feel better about sh*tting on influencers, Hayden Cohen (aka @hayderz), shares his journey on this week’s episode from handling social media for brands to becoming a social media sensation himself. Since 2020, Hayden has been known for his humorous and all-too-accurate impersonations of influencers, reminding us that it pays to take life a little less seriously sometimes. Hayden discusses his early days of content creation, the chaos of his days behind-the scenes managing influencers, and his experiences with influencer culture. He also touches on his life before Instagram-fame, including his close-knit family, his experiences growing up gay, and his first (and last!) relationship with his boyfriend, Aaron. Our conversation sheds light on the balance between online personas and real life, the wild world of influencing, and the importance of remaining grounded despite newfound internet fame. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Hayden: @hayderz Learn more about your ad choices. Visit podcastchoices.com/adchoices Our favorite influencer who makes us all feel better about sh*tting on influencers, Hayden Cohen (aka @hayderz), shares his journey on this week’s episode from handling social media for brands to becoming a social media sensation himself. Since 2020, Hayden has been known for his humorous and all-too-accurate impersonations of influencers, reminding us that it pays to take life a little less seriously sometimes.


Hayden discusses his early days of content creation, the chaos of his days behind-the scenes managing influencers, and his experiences with influencer culture. He also touches on his life before Instagram-fame, including his close-knit family, his experiences growing up gay, and his first (and last!) relationship with his boyfriend, Aaron. Our conversation sheds light on the balance between online personas and real life, the wild world of influencing, and the importance of remaining grounded despite newfound internet fame.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Hayden: @hayderz

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4285 Solo Episode: Embracing life's dualities and what you don't know about friendships In this week's solo episode of 'Brutally Anna,' I'm spilling the tea (or at least, half spilling the tea) on the highs of strutting at Fashion Week to the lows of some unexpected personal drama. We're DIY-ing over in our house as I talk about everything I learned from teaching myself how to replace light fixtures and why you're probably more capable than you're giving yourself credit for. I dive into the unpredictability of life, the Philly Eagles' epic Super Bowl win, and why you don't have to believe in yourself to achieve great things. Lastly, I tackle a listener's question about friendships, sharing my thoughts on why quality beats quantity and why you should always be your own bestie. Tune in for laughs, life lessons, and a whole lot of oversharing. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 13 Feb 2025 10:00:00 -0000 Solo Episode: Embracing life's dualities and what you don't know about friendships full Anna Kai In this week's solo episode of 'Brutally Anna,' I'm spilling the tea (or at least, half spilling the tea) on the highs of strutting at Fashion Week to the lows of some unexpected personal drama. We're DIY-ing over in our house as I talk about everything I learned from teaching myself how to replace light fixtures and why you're probably more capable than you're giving yourself credit for. I dive into the unpredictability of life, the Philly Eagles' epic Super Bowl win, and why you don't have to believe in yourself to achieve great things. Lastly, I tackle a listener's question about friendships, sharing my thoughts on why quality beats quantity and why you should always be your own bestie. Tune in for laughs, life lessons, and a whole lot of oversharing. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices In this week's solo episode of 'Brutally Anna,' I'm spilling the tea (or at least, half spilling the tea) on the highs of strutting at Fashion Week to the lows of some unexpected personal drama. We're DIY-ing over in our house as I talk about everything I learned from teaching myself how to replace light fixtures and why you're probably more capable than you're giving yourself credit for. I dive into the unpredictability of life, the Philly Eagles' epic Super Bowl win, and why you don't have to believe in yourself to achieve great things. Lastly, I tackle a listener's question about friendships, sharing my thoughts on why quality beats quantity and why you should always be your own bestie. Tune in for laughs, life lessons, and a whole lot of oversharing.


Follow Anna:

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2587 Love lessons and life hazards: Joey Zauzig on surviving and thriving On this week's episode, I sit down with influencer and reality TV star Joey Zauzig, about navigating life’s toughest challenges and why sometimes, a six-pack is the best cure for heartbreak. Joey shares his journey from growing up in Fairfax, Virginia, to coming out in high school, facing and leaving an abusive relationship, and eventually establishing a successful career as an influencer and dating advice guru. Joey brings us into his current struggles after dealing with a traumatic home invasion and the emotional turmoil of his divorce. We dive into the complexities of public life, the importance of authenticity, and the need for resilience. Joey emphasizes the significance of personal growth, staying grounded, and the powerful belief that even amidst hardships, the future holds better opportunities. This episode is a raw and insightful look into overcoming personal and professional challenges, highlighting the importance of self-belief and the journey toward becoming one's best self. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Joey: @joeyzauzig Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 10 Feb 2025 10:00:00 -0000 Love lessons and life hazards: Joey Zauzig on surviving and thriving full Anna Kai On this week's episode, I sit down with influencer and reality TV star Joey Zauzig, about navigating life’s toughest challenges and why sometimes, a six-pack is the best cure for heartbreak. Joey shares his journey from growing up in Fairfax, Virginia, to coming out in high school, facing and leaving an abusive relationship, and eventually establishing a successful career as an influencer and dating advice guru. Joey brings us into his current struggles after dealing with a traumatic home invasion and the emotional turmoil of his divorce. We dive into the complexities of public life, the importance of authenticity, and the need for resilience. Joey emphasizes the significance of personal growth, staying grounded, and the powerful belief that even amidst hardships, the future holds better opportunities. This episode is a raw and insightful look into overcoming personal and professional challenges, highlighting the importance of self-belief and the journey toward becoming one's best self. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Joey: @joeyzauzig Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's episode, I sit down with influencer and reality TV star Joey Zauzig, about navigating life’s toughest challenges and why sometimes, a six-pack is the best cure for heartbreak. Joey shares his journey from growing up in Fairfax, Virginia, to coming out in high school, facing and leaving an abusive relationship, and eventually establishing a successful career as an influencer and dating advice guru. Joey brings us into his current struggles after dealing with a traumatic home invasion and the emotional turmoil of his divorce.


We dive into the complexities of public life, the importance of authenticity, and the need for resilience. Joey emphasizes the significance of personal growth, staying grounded, and the powerful belief that even amidst hardships, the future holds better opportunities. This episode is a raw and insightful look into overcoming personal and professional challenges, highlighting the importance of self-belief and the journey toward becoming one's best self.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Joey: @joeyzauzig

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3269 Solo Episode: Date yourself first and other lessons in independence In this week's solo episode, I dive into the fundamental difference between wanting a man rather than feeling like you need one. From my early misconceptions about needing a man to teach me how to handle personal finances to being forced to learn how to handle my own sh*t, I outline the ways in which confidence is an active practice and not something you need to be born with. I answer your voicemails on how to deal with getting over a man who lied to you about his identity and differentiating between intuition and anxiety. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 06 Feb 2025 10:00:00 -0000 Solo Episode: Date yourself first and other lessons in independence full Anna Kai In this week's solo episode, I dive into the fundamental difference between wanting a man rather than feeling like you need one. From my early misconceptions about needing a man to teach me how to handle personal finances to being forced to learn how to handle my own sh*t, I outline the ways in which confidence is an active practice and not something you need to be born with. I answer your voicemails on how to deal with getting over a man who lied to you about his identity and differentiating between intuition and anxiety. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices In this week's solo episode, I dive into the fundamental difference between wanting a man rather than feeling like you need one. From my early misconceptions about needing a man to teach me how to handle personal finances to being forced to learn how to handle my own sh*t, I outline the ways in which confidence is an active practice and not something you need to be born with. I answer your voicemails on how to deal with getting over a man who lied to you about his identity and differentiating between intuition and anxiety.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2727 When he wants to chase you, but he doesn’t want to be with you feat. Aurora Culpo We’re joined by lifestyle influencer and podcast host, Aurora Culpo, this week as she discusses navigating her divorce and how she learned that you really can’t change a man, no matter how many hall passes you give him or how much you spend on lingerie. As always, we love a no-filter, brutally honest woman, and Aurora shows us that there is life after divorce and heartbreak, and there is freedom in the truth after living a lie. Aurora dishes on whether she believes “once a cheater, always a cheater” and how she realized that she wasn’t the exception, she was the rule. We navigate our experience with men who wanted to chase us, but didn’t want to be with us, why we think they do this, and how Aurora’s competitive upbringing affected her relationships as an adult. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Aurora: @auroraculpo Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 03 Feb 2025 10:00:00 -0000 When he wants to chase you, but he doesn’t want to be with you feat. Aurora Culpo full Anna Kai We’re joined by lifestyle influencer and podcast host, Aurora Culpo, this week as she discusses navigating her divorce and how she learned that you really can’t change a man, no matter how many hall passes you give him or how much you spend on lingerie. As always, we love a no-filter, brutally honest woman, and Aurora shows us that there is life after divorce and heartbreak, and there is freedom in the truth after living a lie. Aurora dishes on whether she believes “once a cheater, always a cheater” and how she realized that she wasn’t the exception, she was the rule. We navigate our experience with men who wanted to chase us, but didn’t want to be with us, why we think they do this, and how Aurora’s competitive upbringing affected her relationships as an adult. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Aurora: @auroraculpo Learn more about your ad choices. Visit podcastchoices.com/adchoices We’re joined by lifestyle influencer and podcast host, Aurora Culpo, this week as she discusses navigating her divorce and how she learned that you really can’t change a man, no matter how many hall passes you give him or how much you spend on lingerie. As always, we love a no-filter, brutally honest woman, and Aurora shows us that there is life after divorce and heartbreak, and there is freedom in the truth after living a lie.


Aurora dishes on whether she believes “once a cheater, always a cheater” and how she realized that she wasn’t the exception, she was the rule. We navigate our experience with men who wanted to chase us, but didn’t want to be with us, why we think they do this, and how Aurora’s competitive upbringing affected her relationships as an adult.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Aurora: @auroraculpo

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4569 Solo Episode: Sometimes you were meant to fail so you could succeed elsewhere On this week's solo episode, I'm diving into exposure therapy, how I got over my deep fear of flying, and why I'll always be an aisle seat biddie over a window seat biddie. I overshare about my EDM club days as an NYU college student, what the Avicii documentary can teach us all about why you're not untalented, you're just not in a space that appreciates your talent, and the endless saga to pick a new toilet for our master bathroom. I answer one of your voicemails on how to feel a sense of belonging when all you've grown up with is the feeling of being othered, and why it's important to go granular versus big picture when we're tackling the biggest challenges in our lives. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 30 Jan 2025 10:00:00 -0000 Solo Episode: Sometimes you were meant to fail so you could succeed elsewhere full Anna Kai On this week's solo episode, I'm diving into exposure therapy, how I got over my deep fear of flying, and why I'll always be an aisle seat biddie over a window seat biddie. I overshare about my EDM club days as an NYU college student, what the Avicii documentary can teach us all about why you're not untalented, you're just not in a space that appreciates your talent, and the endless saga to pick a new toilet for our master bathroom. I answer one of your voicemails on how to feel a sense of belonging when all you've grown up with is the feeling of being othered, and why it's important to go granular versus big picture when we're tackling the biggest challenges in our lives. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's solo episode, I'm diving into exposure therapy, how I got over my deep fear of flying, and why I'll always be an aisle seat biddie over a window seat biddie. I overshare about my EDM club days as an NYU college student, what the Avicii documentary can teach us all about why you're not untalented, you're just not in a space that appreciates your talent, and the endless saga to pick a new toilet for our master bathroom.


I answer one of your voicemails on how to feel a sense of belonging when all you've grown up with is the feeling of being othered, and why it's important to go granular versus big picture when we're tackling the biggest challenges in our lives.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2966 Mel Robbins teaches us how to let go and feel worthy of the life and love we want Podcast legend Mel Robbins joins me this week to discuss how to let go, let it be, and why her new book, “The Let Them Theory” will change your life. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice A multiple New York Times bestseller, in-demand public speaker, and the host of the chart-topping Mel Robbins Podcast, Mel answers all of our most pressing questions in life from how to feel worthy, why we need to rebrand our relationship to anxiety, and why feeling “the spark” in a relationship is overrated. We dive into why it’s so difficult to leave a relationship, why women have been conditioned into being people pleasers, and why failure is often the impetus we need to change our lives. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Mel: @melrobbins Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 27 Jan 2025 10:00:00 -0000 Mel Robbins teaches us how to let go and feel worthy of the life and love we want full Anna Kai Podcast legend Mel Robbins joins me this week to discuss how to let go, let it be, and why her new book, “The Let Them Theory” will change your life. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice A multiple New York Times bestseller, in-demand public speaker, and the host of the chart-topping Mel Robbins Podcast, Mel answers all of our most pressing questions in life from how to feel worthy, why we need to rebrand our relationship to anxiety, and why feeling “the spark” in a relationship is overrated. We dive into why it’s so difficult to leave a relationship, why women have been conditioned into being people pleasers, and why failure is often the impetus we need to change our lives. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Mel: @melrobbins Learn more about your ad choices. Visit podcastchoices.com/adchoices Podcast legend Mel Robbins joins me this week to discuss how to let go, let it be, and why her new book, “The Let Them Theory” will change your life.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice


A multiple New York Times bestseller, in-demand public speaker, and the host of the chart-topping Mel Robbins Podcast, Mel answers all of our most pressing questions in life from how to feel worthy, why we need to rebrand our relationship to anxiety, and why feeling “the spark” in a relationship is overrated. We dive into why it’s so difficult to leave a relationship, why women have been conditioned into being people pleasers, and why failure is often the impetus we need to change our lives.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth


Follow Mel: @melrobbins

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4605 Solo Episode: Why you should show up, even if you don't show up pretty This week, it's the mini(est) of all solo episodes as we move into our forever home. I break down why it's important to show up, even when you're tired and feeling oogly moogly, and why we should all place a little less importance of milestone birthdays and start giving ourselves more milestone moments, regardless of what age we are. I'll be back next Thursday with a full solo episode where I answer your voicemails, so head on over to speakpipe.com/brutallyannapodcast to leave me a message. Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 23 Jan 2025 10:00:00 -0000 Solo Episode: Why you should show up, even if you don't show up pretty full Anna Kai This week, it's the mini(est) of all solo episodes as we move into our forever home. I break down why it's important to show up, even when you're tired and feeling oogly moogly, and why we should all place a little less importance of milestone birthdays and start giving ourselves more milestone moments, regardless of what age we are. I'll be back next Thursday with a full solo episode where I answer your voicemails, so head on over to speakpipe.com/brutallyannapodcast to leave me a message. Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, it's the mini(est) of all solo episodes as we move into our forever home. I break down why it's important to show up, even when you're tired and feeling oogly moogly, and why we should all place a little less importance of milestone birthdays and start giving ourselves more milestone moments, regardless of what age we are. I'll be back next Thursday with a full solo episode where I answer your voicemails, so head on over to speakpipe.com/brutallyannapodcast to leave me a message.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 642 Why you should stop thinking and start doing with Mathilde Thomas, co-founder of Caudalie If there's anything Mathilde Thomas' life can teach is, it's that we don't need to be ready in order to start. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, love and money, marriage advice The co-founder of the viral French skincare brand, Caudalie, Mathilde joins me in the studio to discuss how she met her husband and his decidedly unconventional "pick-up line", why sometimes, taking a break from your relationship can ultimately strengthen it, and how she and her husband managed to take a struggling start-up to an internationally renowned skincare brand. Mathilde shares why believing in yourself and your product, even if no one else does, can lead to great results, and why picking your life partner also determines your life's work. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Mathilde & Caudalie @mathildethomas @caudalie Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 20 Jan 2025 10:00:00 -0000 Why you should stop thinking and start doing with Mathilde Thomas, co-founder of Caudalie full Anna Kai If there's anything Mathilde Thomas' life can teach is, it's that we don't need to be ready in order to start. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, love and money, marriage advice The co-founder of the viral French skincare brand, Caudalie, Mathilde joins me in the studio to discuss how she met her husband and his decidedly unconventional "pick-up line", why sometimes, taking a break from your relationship can ultimately strengthen it, and how she and her husband managed to take a struggling start-up to an internationally renowned skincare brand. Mathilde shares why believing in yourself and your product, even if no one else does, can lead to great results, and why picking your life partner also determines your life's work. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Mathilde & Caudalie @mathildethomas @caudalie Learn more about your ad choices. Visit podcastchoices.com/adchoices If there's anything Mathilde Thomas' life can teach is, it's that we don't need to be ready in order to start.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, love and money, marriage advice


The co-founder of the viral French skincare brand, Caudalie, Mathilde joins me in the studio to discuss how she met her husband and his decidedly unconventional "pick-up line", why sometimes, taking a break from your relationship can ultimately strengthen it, and how she and her husband managed to take a struggling start-up to an internationally renowned skincare brand.


Mathilde shares why believing in yourself and your product, even if no one else does, can lead to great results, and why picking your life partner also determines your life's work.


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]]> 3172 Solo Episode: The LA Fires, my most humbling moment, and how to deal with friend breakups This week, I'm discussing the LA fires, the devastation of losing your home and why insurance doesn't cover the most important parts of what made a house our home. And, since I'm just freezing in sub-zero Connecticut temperatures rather than experiencing the hellfire in LA, I decide my pride is fair game to take shots at in a feeble attempt to make you all chuckle a little by divulging way too much information about my most humbling experience ever (hint: diarrhea in a fridge). I answer your voicemails on how to mourn the loss of platonic friendships you thought would last forever, and where to start when you're trying to break the cycle of generational trauma. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 16 Jan 2025 10:00:00 -0000 The LA Fires, my most humbling moment, and how to deal with friend breakups full Anna Kai This week, I'm discussing the LA fires, the devastation of losing your home and why insurance doesn't cover the most important parts of what made a house our home. And, since I'm just freezing in sub-zero Connecticut temperatures rather than experiencing the hellfire in LA, I decide my pride is fair game to take shots at in a feeble attempt to make you all chuckle a little by divulging way too much information about my most humbling experience ever (hint: diarrhea in a fridge). I answer your voicemails on how to mourn the loss of platonic friendships you thought would last forever, and where to start when you're trying to break the cycle of generational trauma. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I'm discussing the LA fires, the devastation of losing your home and why insurance doesn't cover the most important parts of what made a house our home. And, since I'm just freezing in sub-zero Connecticut temperatures rather than experiencing the hellfire in LA, I decide my pride is fair game to take shots at in a feeble attempt to make you all chuckle a little by divulging way too much information about my most humbling experience ever (hint: diarrhea in a fridge). I answer your voicemails on how to mourn the loss of platonic friendships you thought would last forever, and where to start when you're trying to break the cycle of generational trauma.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3295 Tough times are temporary and the power of female friendships with Taryn Delanie Smith Former Miss New York, social media star and TV host Taryn Delanie Smith’s life could’ve gone in a very different direction if it wasn’t for the power of her single mother and the community of women who raised her. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice On this week’s episode, we unpack the ways in which Taryn’s life worked out exactly the way it was supposed to, even when it wasn’t going according to her plans. From her days as an aspiring U.N. diplomat to competing in Miss America, Taryn unpacks all the reasons why it took her eight years of dating before marrying her husband and why she thinks that sometimes, the best advice to take is your own. For anyone who has ever wondered when their life is going to begin, my conversation with Taryn shows us all that sometimes, the best things in life happen to us while we’re waiting to start living. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Taryn @taryndelaniesmith Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 13 Jan 2025 10:00:00 -0000 Tough times are temporary and the power of female friendships with Taryn Delanie Smith full Anna Kai Former Miss New York, social media star and TV host Taryn Delanie Smith’s life could’ve gone in a very different direction if it wasn’t for the power of her single mother and the community of women who raised her. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice On this week’s episode, we unpack the ways in which Taryn’s life worked out exactly the way it was supposed to, even when it wasn’t going according to her plans. From her days as an aspiring U.N. diplomat to competing in Miss America, Taryn unpacks all the reasons why it took her eight years of dating before marrying her husband and why she thinks that sometimes, the best advice to take is your own. For anyone who has ever wondered when their life is going to begin, my conversation with Taryn shows us all that sometimes, the best things in life happen to us while we’re waiting to start living. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Taryn @taryndelaniesmith Learn more about your ad choices. Visit podcastchoices.com/adchoices Former Miss New York, social media star and TV host Taryn Delanie Smith’s life could’ve gone in a very different direction if it wasn’t for the power of her single mother and the community of women who raised her.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice


On this week’s episode, we unpack the ways in which Taryn’s life worked out exactly the way it was supposed to, even when it wasn’t going according to her plans. From her days as an aspiring U.N. diplomat to competing in Miss America, Taryn unpacks all the reasons why it took her eight years of dating before marrying her husband and why she thinks that sometimes, the best advice to take is your own.


For anyone who has ever wondered when their life is going to begin, my conversation with Taryn shows us all that sometimes, the best things in life happen to us while we’re waiting to start living.


Follow Anna: 

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Follow Taryn @taryndelaniesmith

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]]> 4360 Solo Episode: When he loves you, but can't be with you, and why you should gaslight yourself Don't do as Bernie Madoff did (ie. commit history's largest Ponzi scheme), but you can learn from why he was able to do what he did. This week, I'm discussing why sometimes, gaslighting yourself into believing you're capable of something well before you actually do it can be a self-fulfilling prophecy that snowballs into others believing in you, too. If you've ever written yourself off, tune into this episode and hear the stories that inspired me to create possibility where I once found impossibility. I answer your voicemails on why you're still feeling heartbroken after a breakup even when the rest of your life is getting better, and what to do when he says he still loves you, but just can't be with you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 09 Jan 2025 10:00:00 -0000 Solo Episode: When he loves you, but can't be with you, and why you should gaslight yourself full Anna Kai Don't do as Bernie Madoff did (ie. commit history's largest Ponzi scheme), but you can learn from why he was able to do what he did. This week, I'm discussing why sometimes, gaslighting yourself into believing you're capable of something well before you actually do it can be a self-fulfilling prophecy that snowballs into others believing in you, too. If you've ever written yourself off, tune into this episode and hear the stories that inspired me to create possibility where I once found impossibility. I answer your voicemails on why you're still feeling heartbroken after a breakup even when the rest of your life is getting better, and what to do when he says he still loves you, but just can't be with you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Don't do as Bernie Madoff did (ie. commit history's largest Ponzi scheme), but you can learn from why he was able to do what he did. This week, I'm discussing why sometimes, gaslighting yourself into believing you're capable of something well before you actually do it can be a self-fulfilling prophecy that snowballs into others believing in you, too. If you've ever written yourself off, tune into this episode and hear the stories that inspired me to create possibility where I once found impossibility. I answer your voicemails on why you're still feeling heartbroken after a breakup even when the rest of your life is getting better, and what to do when he says he still loves you, but just can't be with you.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3314 Why you should get a prenup and how to be the main character feat. Vivian Tu aka YourRichBFF We're joined this week with Vivian Tu as she doles out the advice we all need to hear on how to stop settling for less than what you deserve whether that's at work or in your love life. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, prenups, marriage advice Vivian's story shows us all how to stop letting other people write the narrative to your life and why you shouldn't avoid doing things just because they're hard. On this week's episode, we discuss harmful stereotypes and narratives about Asian women, why she left her first career on Wall Street and then her second career at BuzzFeed, and why she thinks everyone should get a prenup before getting married. We talk about that time she moved in with her boyfriend after one month of dating, whether she thinks money can actually make you happier, and why you can tell a lot about a person from the way they treat money. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Vivian: @yourrichbff Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 06 Jan 2025 10:00:00 -0000 Why you should get a prenup and how to be the main character feat. Vivian Tu aka YourRichBFF full Anna Kai We're joined this week with Vivian Tu as she doles out the advice we all need to hear on how to stop settling for less than what you deserve whether that's at work or in your love life. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, prenups, marriage advice Vivian's story shows us all how to stop letting other people write the narrative to your life and why you shouldn't avoid doing things just because they're hard. On this week's episode, we discuss harmful stereotypes and narratives about Asian women, why she left her first career on Wall Street and then her second career at BuzzFeed, and why she thinks everyone should get a prenup before getting married. We talk about that time she moved in with her boyfriend after one month of dating, whether she thinks money can actually make you happier, and why you can tell a lot about a person from the way they treat money. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Vivian: @yourrichbff Learn more about your ad choices. Visit podcastchoices.com/adchoices We're joined this week with Vivian Tu as she doles out the advice we all need to hear on how to stop settling for less than what you deserve whether that's at work or in your love life.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, prenups, marriage advice


Vivian's story shows us all how to stop letting other people write the narrative to your life and why you shouldn't avoid doing things just because they're hard. On this week's episode, we discuss harmful stereotypes and narratives about Asian women, why she left her first career on Wall Street and then her second career at BuzzFeed, and why she thinks everyone should get a prenup before getting married. We talk about that time she moved in with her boyfriend after one month of dating, whether she thinks money can actually make you happier, and why you can tell a lot about a person from the way they treat money.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Vivian: @yourrichbff

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4617 Solo Episode: When your year-in-review didn't live up to your expectations and my mantra for 2025 Happy New Year to all my biddies! This week, I'm breaking down how to appreciate your year-in-review, even if nothing profound or life-changing happened in 2024, and why you probably made more progress than you think you did. We're discussing how to handle those *weird* feelings you get when it feels like everyone around you cured cancer and went to the moon and you, on the other hand, managed to barely survive the year that just passed. I discuss how my faith and trust in God has helped me help myself and why we should embrace and claim the bad days that lie ahead in the new year just as much as the good days. You asked, I answered - how do you handle retroactive jealousy when your partner is the most wonderful non-Chad ever, but you can't seem to get over your feelings about his ex? Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 02 Jan 2025 19:55:00 -0000 Solo Episode: When your year-in-review didn't live up to your expectations and my mantra for 2025 full Anna Kai Happy New Year to all my biddies! This week, I'm breaking down how to appreciate your year-in-review, even if nothing profound or life-changing happened in 2024, and why you probably made more progress than you think you did. We're discussing how to handle those *weird* feelings you get when it feels like everyone around you cured cancer and went to the moon and you, on the other hand, managed to barely survive the year that just passed. I discuss how my faith and trust in God has helped me help myself and why we should embrace and claim the bad days that lie ahead in the new year just as much as the good days. You asked, I answered - how do you handle retroactive jealousy when your partner is the most wonderful non-Chad ever, but you can't seem to get over your feelings about his ex? Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Happy New Year to all my biddies! This week, I'm breaking down how to appreciate your year-in-review, even if nothing profound or life-changing happened in 2024, and why you probably made more progress than you think you did. We're discussing how to handle those *weird* feelings you get when it feels like everyone around you cured cancer and went to the moon and you, on the other hand, managed to barely survive the year that just passed.


I discuss how my faith and trust in God has helped me help myself and why we should embrace and claim the bad days that lie ahead in the new year just as much as the good days. You asked, I answered - how do you handle retroactive jealousy when your partner is the most wonderful non-Chad ever, but you can't seem to get over your feelings about his ex?


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2694 Date them until you hate them and why love isn’t enough with matchmaker Aleeza Ben Shalmon, the star of Netflix’s Jewish Matchmaking If it’s not love at first sight…try again. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money With decades of professional matchmaking wisdom, Netflix-star Aleeza Ben Shalom sits down and answers my questions on whether soulmates exist, why it doesn’t have to be love at first sight in order for it to be everlasting love, and whether there is someone out there for everyone.  What first started out as a hobby has now turned into a full-fledged business for Aleeza, who has focused on pairing marriage-minded individuals since 2007 first in the U.S. She offers her advice on how couples should handle conversations around money, religion, and how to handle awkward questions from family members at the holidays. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Aleeza: @aleezabenshalom Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 30 Dec 2024 10:00:00 -0000 Date them until you hate them and why love isn’t enough with matchmaker Aleeza Ben Shalmon, the star of Netflix’s Jewish Matchmaking full Anna Kai If it’s not love at first sight…try again. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money With decades of professional matchmaking wisdom, Netflix-star Aleeza Ben Shalom sits down and answers my questions on whether soulmates exist, why it doesn’t have to be love at first sight in order for it to be everlasting love, and whether there is someone out there for everyone.  What first started out as a hobby has now turned into a full-fledged business for Aleeza, who has focused on pairing marriage-minded individuals since 2007 first in the U.S. She offers her advice on how couples should handle conversations around money, religion, and how to handle awkward questions from family members at the holidays. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Aleeza: @aleezabenshalom Learn more about your ad choices. Visit podcastchoices.com/adchoices If it’s not love at first sight…try again.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


With decades of professional matchmaking wisdom, Netflix-star Aleeza Ben Shalom sits down and answers my questions on whether soulmates exist, why it doesn’t have to be love at first sight in order for it to be everlasting love, and whether there is someone out there for everyone. 


What first started out as a hobby has now turned into a full-fledged business for Aleeza, who has focused on pairing marriage-minded individuals since 2007 first in the U.S. She offers her advice on how couples should handle conversations around money, religion, and how to handle awkward questions from family members at the holidays.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Aleeza: @aleezabenshalom

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3500 Solo Episode: Luigi Mangione and why women fall in love with prisoners On this week's solo episode, I'm breaking down my thoughts on our collective obsession with Luigi Mangione, the psychology behind why women fall in love with prisoners and how those theories apply to why you just can't seem to quit your situationship. I'm bringing it back to the only class I'll really ever remember from my days at NYU, the relativity of morality, and whether all is fair in love and war. On this week's voicemails, I answer your questions on how to rebuild your life from ground zero and what it truly means to be a man when your definition of manhood doesn't fit everyone else's definition. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 26 Dec 2024 10:00:00 -0000 Luigi Mangione and why women fall in love with prisoners full Anna Kai On this week's solo episode, I'm breaking down my thoughts on our collective obsession with Luigi Mangione, the psychology behind why women fall in love with prisoners and how those theories apply to why you just can't seem to quit your situationship. I'm bringing it back to the only class I'll really ever remember from my days at NYU, the relativity of morality, and whether all is fair in love and war. On this week's voicemails, I answer your questions on how to rebuild your life from ground zero and what it truly means to be a man when your definition of manhood doesn't fit everyone else's definition. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's solo episode, I'm breaking down my thoughts on our collective obsession with Luigi Mangione, the psychology behind why women fall in love with prisoners and how those theories apply to why you just can't seem to quit your situationship. I'm bringing it back to the only class I'll really ever remember from my days at NYU, the relativity of morality, and whether all is fair in love and war. On this week's voicemails, I answer your questions on how to rebuild your life from ground zero and what it truly means to be a man when your definition of manhood doesn't fit everyone else's definition.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2774 How to stop being depressed and signs you’re dating a narcissist with Dr. Jaime Zuckerman What’s the difference between a narcissistic person and a selfish person? Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I’m joined by Dr. Jaime Zuckerman, a licensed clinical psychologist and narcissistic abuse expert to discuss all the ways we can spot narcissistic personality disorder early on a relationship, how to deal with a narcissistic family member, and finally, Dr. Z answers whether it’s possible to marry and live happily ever after with a narcissist. For those struggling with depression, Dr. Z offers her practical and actionable advice on what you can do to start to feel good again and why healing has nothing to do with gratitude. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Dr. Z @dr.z_psychologist Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 23 Dec 2024 10:00:00 -0000 How to stop being depressed and signs you’re dating a narcissist with Dr. Jaime Zuckerman full Anna Kai What’s the difference between a narcissistic person and a selfish person? Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I’m joined by Dr. Jaime Zuckerman, a licensed clinical psychologist and narcissistic abuse expert to discuss all the ways we can spot narcissistic personality disorder early on a relationship, how to deal with a narcissistic family member, and finally, Dr. Z answers whether it’s possible to marry and live happily ever after with a narcissist. For those struggling with depression, Dr. Z offers her practical and actionable advice on what you can do to start to feel good again and why healing has nothing to do with gratitude. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Dr. Z @dr.z_psychologist Learn more about your ad choices. Visit podcastchoices.com/adchoices What’s the difference between a narcissistic person and a selfish person?


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


This week, I’m joined by Dr. Jaime Zuckerman, a licensed clinical psychologist and narcissistic abuse expert to discuss all the ways we can spot narcissistic personality disorder early on a relationship, how to deal with a narcissistic family member, and finally, Dr. Z answers whether it’s possible to marry and live happily ever after with a narcissist.


For those struggling with depression, Dr. Z offers her practical and actionable advice on what you can do to start to feel good again and why healing has nothing to do with gratitude.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Dr. Z @dr.z_psychologist

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3714 Solo Episode: The art of being alone at the holidays and how long does it actually take to get over a breakup Being alone (at the holidays or otherwise) doesn't mean you have to be lonely. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice On this week's solo episode, I discuss the choice to be alone at the holidays and why we all need to embrace aloneness, even if it completely and utterly sucks at first. I break down why I spent a lot of time with friends and men that didn't make me feel good in my twenties and how learning to be alone gave me everything I wanted in life. You asked in your voicemails and I answered on how to get over heartbreak when you're doing everything right, but still feel devastated, and how to stop blaming yourself for the end of a relationship when it was everyone's fault and no one's fault all at the same time. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 19 Dec 2024 10:00:00 -0000 Solo Episode: The art of being alone at the holidays and how long does it actually take to get over a breakup full Anna Kai Being alone (at the holidays or otherwise) doesn't mean you have to be lonely. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice On this week's solo episode, I discuss the choice to be alone at the holidays and why we all need to embrace aloneness, even if it completely and utterly sucks at first. I break down why I spent a lot of time with friends and men that didn't make me feel good in my twenties and how learning to be alone gave me everything I wanted in life. You asked in your voicemails and I answered on how to get over heartbreak when you're doing everything right, but still feel devastated, and how to stop blaming yourself for the end of a relationship when it was everyone's fault and no one's fault all at the same time. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Being alone (at the holidays or otherwise) doesn't mean you have to be lonely.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage advice

On this week's solo episode, I discuss the choice to be alone at the holidays and why we all need to embrace aloneness, even if it completely and utterly sucks at first. I break down why I spent a lot of time with friends and men that didn't make me feel good in my twenties and how learning to be alone gave me everything I wanted in life.

You asked in your voicemails and I answered on how to get over heartbreak when you're doing everything right, but still feel devastated, and how to stop blaming yourself for the end of a relationship when it was everyone's fault and no one's fault all at the same time.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3549 Why you should go for the nerd with Brandon Berman and Harrison Forman, the creators of UpDating This week, I sit down with Brandon Berman and Harrison Forman, the creators of the viral live dating show, UpDating, where contestants date blindfolded in front of a live audience. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money We discuss everything from whether they believe if men and women can really be just friends, the awkward beginnings of both of their LTRs and how they found success by not taking themselves too seriously. Brandon reveals why he gave his girlfriend an ultimatum two weeks into their relationship, while Harrison shows us all that sometimes, you haven’t found love because you’re not looking in the right place. We dive into where they believe all the good men have really gone (spoiler: some of them can be found at the UpDating after parties) and how they grew their live show from humble beginnings. For anyone who’s ever felt like they’ve been counted out, Brandon and Harrison want you to know that creating your own lane is always better than trying to compete in someone else’s. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Brandon & Harrison: @updatingshow @bermmy16 @htforman Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 16 Dec 2024 10:00:00 -0000 Why you should go for the nerd and the power of creating your own lane with Brandon Berman and Harrison Forman, the creators of UpDating full 10 Anna Kai This week, I sit down with Brandon Berman and Harrison Forman, the creators of the viral live dating show, UpDating, where contestants date blindfolded in front of a live audience. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money We discuss everything from whether they believe if men and women can really be just friends, the awkward beginnings of both of their LTRs and how they found success by not taking themselves too seriously. Brandon reveals why he gave his girlfriend an ultimatum two weeks into their relationship, while Harrison shows us all that sometimes, you haven’t found love because you’re not looking in the right place. We dive into where they believe all the good men have really gone (spoiler: some of them can be found at the UpDating after parties) and how they grew their live show from humble beginnings. For anyone who’s ever felt like they’ve been counted out, Brandon and Harrison want you to know that creating your own lane is always better than trying to compete in someone else’s. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Brandon & Harrison: @updatingshow @bermmy16 @htforman Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I sit down with Brandon Berman and Harrison Forman, the creators of the viral live dating show, UpDating, where contestants date blindfolded in front of a live audience.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


We discuss everything from whether they believe if men and women can really be just friends, the awkward beginnings of both of their LTRs and how they found success by not taking themselves too seriously. Brandon reveals why he gave his girlfriend an ultimatum two weeks into their relationship, while Harrison shows us all that sometimes, you haven’t found love because you’re not looking in the right place.


We dive into where they believe all the good men have really gone (spoiler: some of them can be found at the UpDating after parties) and how they grew their live show from humble beginnings. For anyone who’s ever felt like they’ve been counted out, Brandon and Harrison want you to know that creating your own lane is always better than trying to compete in someone else’s.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Brandon & Harrison: @updatingshow @bermmy16 @htforman

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 5061 Solo Episode: You can be married to a cheater, but don't date a cheater and why some long distance relationships fail This week, I'm breaking down my thoughts on Netflix's Ashley Madison documentary and the Laci Peterson story. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, cheating, infidelity, narcissism, self-help Tune in for my thoughts on why (some) people cheat, why I think it's okay to be married to a cheater, but not to date a cheater, and how to spot signs of love bombing. We dive into the reasons why it's dangerous to commit to a relationship or a marriage before you've committed to what you want in life and how to spot the difference between someone who loves you and someone who loves what you do for them. I answer your voicemails on why a long-distance relationship turned cold once it was no longer long distance, and how to get your power back after getting your heart broken and watching your ex move on before you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 12 Dec 2024 10:00:00 -0000 Solo Episode: You can be married to a cheater, but don't date a cheater and how to get your power back after a break-up full Anna Kai This week, I'm breaking down my thoughts on Netflix's Ashley Madison documentary and the Laci Peterson story. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, cheating, infidelity, narcissism, self-help Tune in for my thoughts on why (some) people cheat, why I think it's okay to be married to a cheater, but not to date a cheater, and how to spot signs of love bombing. We dive into the reasons why it's dangerous to commit to a relationship or a marriage before you've committed to what you want in life and how to spot the difference between someone who loves you and someone who loves what you do for them. I answer your voicemails on why a long-distance relationship turned cold once it was no longer long distance, and how to get your power back after getting your heart broken and watching your ex move on before you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices This week, I'm breaking down my thoughts on Netflix's Ashley Madison documentary and the Laci Peterson story.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, cheating, infidelity, narcissism, self-help


Tune in for my thoughts on why (some) people cheat, why I think it's okay to be married to a cheater, but not to date a cheater, and how to spot signs of love bombing. We dive into the reasons why it's dangerous to commit to a relationship or a marriage before you've committed to what you want in life and how to spot the difference between someone who loves you and someone who loves what you do for them. I answer your voicemails on why a long-distance relationship turned cold once it was no longer long distance, and how to get your power back after getting your heart broken and watching your ex move on before you.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3120 What cancer taught Kaitlin Reagan about forgiveness Kaitlin Reagan knows a thing or two about letting go. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money In this week’s episode, I sit down with Kaitlin to talk about her journey as the daughter of a single mom in Brooklyn to TikTok stardom and losing her boyfriend, Francesco, to cancer along the way. Find out why Kaitlin doesn’t believe in long distance relationships, how she overcame her family history of drug addiction, and why she’s done trying to fit into anyone else’s life but her own. For anyone who has ever been angry at the cards they were dealt, Kaitlin’s story shows us all that it’s not about what happens to us, but what we do with what happens to us that determines our fate. We muse on whether it’s really possible to find everything you want in a man, why she still wears a promise ring from Francesco, and how she knew she was finally able to move on after his passing. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kaitlin @kaitlin_reagan Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 09 Dec 2024 10:00:00 -0000 What her boyfriend’s cancer diagnosis taught Kaitlin Reagan about forgiveness full 9 Anna Kai Kaitlin Reagan knows a thing or two about letting go. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money In this week’s episode, I sit down with Kaitlin to talk about her journey as the daughter of a single mom in Brooklyn to TikTok stardom and losing her boyfriend, Francesco, to cancer along the way. Find out why Kaitlin doesn’t believe in long distance relationships, how she overcame her family history of drug addiction, and why she’s done trying to fit into anyone else’s life but her own. For anyone who has ever been angry at the cards they were dealt, Kaitlin’s story shows us all that it’s not about what happens to us, but what we do with what happens to us that determines our fate. We muse on whether it’s really possible to find everything you want in a man, why she still wears a promise ring from Francesco, and how she knew she was finally able to move on after his passing. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kaitlin @kaitlin_reagan Learn more about your ad choices. Visit podcastchoices.com/adchoices Kaitlin Reagan knows a thing or two about letting go.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


In this week’s episode, I sit down with Kaitlin to talk about her journey as the daughter of a single mom in Brooklyn to TikTok stardom and losing her boyfriend, Francesco, to cancer along the way. Find out why Kaitlin doesn’t believe in long distance relationships, how she overcame her family history of drug addiction, and why she’s done trying to fit into anyone else’s life but her own.


For anyone who has ever been angry at the cards they were dealt, Kaitlin’s story shows us all that it’s not about what happens to us, but what we do with what happens to us that determines our fate. We muse on whether it’s really possible to find everything you want in a man, why she still wears a promise ring from Francesco, and how she knew she was finally able to move on after his passing.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Kaitlin @kaitlin_reagan

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4496 Solo Episode: My emotional baggage around Christmas cards and dating advice on what to do when the chemistry is there, but the sex isn't Emotional baggage comes in many forms and mine comes when it's time to make our Christmas card. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I discuss the culture of Christmas cards and all the reasons why smiling photos of perfect families on a 5x7 make me feel some type of way and what to remember this holiday season if your life is looking a little less than picture perfect. I dish on what my "honest" Christmas card would say if I had carte blanche to write what I wanted on the back of our card and why sometimes, you're not behind, you're just on a different path. Tune in as I answer voicemails on whether you should choose love or money and just how important sex is in a relationship. Leave me a voicemail: speakpipe.com/brutallyannapodcast Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 05 Dec 2024 10:00:00 -0000 Solo Episode: My emotional baggage around Christmas cards and dating advice on what to do when the chemistry is there, but the sex isn't full Anna Kai Emotional baggage comes in many forms and mine comes when it's time to make our Christmas card. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I discuss the culture of Christmas cards and all the reasons why smiling photos of perfect families on a 5x7 make me feel some type of way and what to remember this holiday season if your life is looking a little less than picture perfect. I dish on what my "honest" Christmas card would say if I had carte blanche to write what I wanted on the back of our card and why sometimes, you're not behind, you're just on a different path. Tune in as I answer voicemails on whether you should choose love or money and just how important sex is in a relationship. Leave me a voicemail: speakpipe.com/brutallyannapodcast Learn more about your ad choices. Visit podcastchoices.com/adchoices Emotional baggage comes in many forms and mine comes when it's time to make our Christmas card.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

This week, I discuss the culture of Christmas cards and all the reasons why smiling photos of perfect families on a 5x7 make me feel some type of way and what to remember this holiday season if your life is looking a little less than picture perfect. I dish on what my "honest" Christmas card would say if I had carte blanche to write what I wanted on the back of our card and why sometimes, you're not behind, you're just on a different path. Tune in as I answer voicemails on whether you should choose love or money and just how important sex is in a relationship.

Leave me a voicemail: speakpipe.com/brutallyannapodcast

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3790 How to laugh at death with Kelly Rizzo Kelly Rizzo wants us all to know that it’s okay to laugh at death. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money She’s the creator of the award-winning production company, Eat Travel Rock Productions and recently competed on Fox’s Special Forces, but Kelly and I sit down today to talk more about how losing her husband, Bob Saget, forced her to learn that there is humor to be found, even in times of great loss. We tackle the topic of deciding not to have children, why it’s okay to choose the man over the life other people expect you to live, and how she’s managed to start over after having the rug pulled out from underneath her. For anyone who’s grappling with the loss of a spouse, Kelly wants us all to know that it’s possible to move forward and find love again without negating the love you once had. We discuss whether she would ever go on Special Forces again, her journey from atheism to Christianity and why she believes finding peace is more important than finding closure. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kelly @kellyrizzo Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 02 Dec 2024 10:00:00 -0000 How to laugh at death and finding love again after loss with Kelly Rizzo full 8 Anna Kai Kelly Rizzo wants us all to know that it’s okay to laugh at death. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money She’s the creator of the award-winning production company, Eat Travel Rock Productions and recently competed on Fox’s Special Forces, but Kelly and I sit down today to talk more about how losing her husband, Bob Saget, forced her to learn that there is humor to be found, even in times of great loss. We tackle the topic of deciding not to have children, why it’s okay to choose the man over the life other people expect you to live, and how she’s managed to start over after having the rug pulled out from underneath her. For anyone who’s grappling with the loss of a spouse, Kelly wants us all to know that it’s possible to move forward and find love again without negating the love you once had. We discuss whether she would ever go on Special Forces again, her journey from atheism to Christianity and why she believes finding peace is more important than finding closure. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kelly @kellyrizzo Learn more about your ad choices. Visit podcastchoices.com/adchoices Kelly Rizzo wants us all to know that it’s okay to laugh at death.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


She’s the creator of the award-winning production company, Eat Travel Rock Productions and recently competed on Fox’s Special Forces, but Kelly and I sit down today to talk more about how losing her husband, Bob Saget, forced her to learn that there is humor to be found, even in times of great loss. We tackle the topic of deciding not to have children, why it’s okay to choose the man over the life other people expect you to live, and how she’s managed to start over after having the rug pulled out from underneath her.


For anyone who’s grappling with the loss of a spouse, Kelly wants us all to know that it’s possible to move forward and find love again without negating the love you once had. We discuss whether she would ever go on Special Forces again, her journey from atheism to Christianity and why she believes finding peace is more important than finding closure.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Kelly @kellyrizzo

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4617 Solo Episode: How a psychic led me to back to Zoloft Happy Thanksgiving to all my American biddies and this Thanksgiving, I'm grateful for the psychic that made me realize that I needed to go back on Zoloft. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I'm discussing all things antidepressants, medication, and why a bad reading from a psychic led me to get back onto a good path with my mental health. I answer your questions about how to disentangle your life from a long-term partner and how to get over your first love when it feels like you'll never be loved again and, how to handle Thanksgiving when you have nothing to be grateful for. Leave me a voice at speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 28 Nov 2024 10:00:00 -0000 full 11 Anna Kai Happy Thanksgiving to all my American biddies and this Thanksgiving, I'm grateful for the psychic that made me realize that I needed to go back on Zoloft. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I'm discussing all things antidepressants, medication, and why a bad reading from a psychic led me to get back onto a good path with my mental health. I answer your questions about how to disentangle your life from a long-term partner and how to get over your first love when it feels like you'll never be loved again and, how to handle Thanksgiving when you have nothing to be grateful for. Leave me a voice at speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Happy Thanksgiving to all my American biddies and this Thanksgiving, I'm grateful for the psychic that made me realize that I needed to go back on Zoloft.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


This week, I'm discussing all things antidepressants, medication, and why a bad reading from a psychic led me to get back onto a good path with my mental health. I answer your questions about how to disentangle your life from a long-term partner and how to get over your first love when it feels like you'll never be loved again and, how to handle Thanksgiving when you have nothing to be grateful for.


Leave me a voice at speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2825 The power of not belonging with Ava Lee What’s it like to feel like an outsider your entire life? Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, we sit down with beauty and skincare influencer, Ava Lee, on life before going viral for her “jelloskin” tips and the power of reinventing yourself. Ava dishes on growing up in Shanghai and her first time in America as a college student at Notre Dame. We unpack the nuances of the Asian-American experience, assimilation, and how sometimes, we have to be who we are not in order to discover who we are. Ava and I detail our early days in social media and how we got over the cringe of being “that girl who thinks she’s an influencer”, how serving sizes are a uniquely American concept, and how she healed herself by going back to her eastern gastronomic roots. For all the biddies who believe in second chances, tune in to find out why it was not love at first sight for Ava and her husband Ben, and who her favorite ex was. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Ava @glowwithava @byava Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 25 Nov 2024 10:00:00 -0000 The power of not belonging with Ava Lee full 7 Anna Kai What’s it like to feel like an outsider your entire life? Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, we sit down with beauty and skincare influencer, Ava Lee, on life before going viral for her “jelloskin” tips and the power of reinventing yourself. Ava dishes on growing up in Shanghai and her first time in America as a college student at Notre Dame. We unpack the nuances of the Asian-American experience, assimilation, and how sometimes, we have to be who we are not in order to discover who we are. Ava and I detail our early days in social media and how we got over the cringe of being “that girl who thinks she’s an influencer”, how serving sizes are a uniquely American concept, and how she healed herself by going back to her eastern gastronomic roots. For all the biddies who believe in second chances, tune in to find out why it was not love at first sight for Ava and her husband Ben, and who her favorite ex was. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Ava @glowwithava @byava Learn more about your ad choices. Visit podcastchoices.com/adchoices What’s it like to feel like an outsider your entire life?


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


On this week’s episode, we sit down with beauty and skincare influencer, Ava Lee, on life before going viral for her “jelloskin” tips and the power of reinventing yourself. Ava dishes on growing up in Shanghai and her first time in America as a college student at Notre Dame. We unpack the nuances of the Asian-American experience, assimilation, and how sometimes, we have to be who we are not in order to discover who we are.


Ava and I detail our early days in social media and how we got over the cringe of being “that girl who thinks she’s an influencer”, how serving sizes are a uniquely American concept, and how she healed herself by going back to her eastern gastronomic roots. For all the biddies who believe in second chances, tune in to find out why it was not love at first sight for Ava and her husband Ben, and who her favorite ex was.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Ava @glowwithava @byava

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 3883 Solo Episode: Your struggle is your superpower and other unfiltered thoughts from my hotel room in LA On this week's solo episode, I'm coming to you, kind of live, from my hotel room in LA with a mixture of gratitude and Wellbutrin. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money We're reminding ourselves that our mental state is not always an accurate reflection of what the reality is around us, and that having sad moments doesn't make us sad people, it just makes us people. For those of you who find yourselves in struggle city this time of year, tune in for my advice on how to light the fire under you to get yourself going when you're in a rut, and what to do when you're tired of dating, but not tired of hoping to find love. I answer your voicemails about how to stop being fetishized as an Asian-American woman on dates, and how to cope with your ex moving on and getting engaged to someone else. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 21 Nov 2024 10:00:00 -0000 full Anna Kai On this week's solo episode, I'm coming to you, kind of live, from my hotel room in LA with a mixture of gratitude and Wellbutrin. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money We're reminding ourselves that our mental state is not always an accurate reflection of what the reality is around us, and that having sad moments doesn't make us sad people, it just makes us people. For those of you who find yourselves in struggle city this time of year, tune in for my advice on how to light the fire under you to get yourself going when you're in a rut, and what to do when you're tired of dating, but not tired of hoping to find love. I answer your voicemails about how to stop being fetishized as an Asian-American woman on dates, and how to cope with your ex moving on and getting engaged to someone else. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's solo episode, I'm coming to you, kind of live, from my hotel room in LA with a mixture of gratitude and Wellbutrin.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


We're reminding ourselves that our mental state is not always an accurate reflection of what the reality is around us, and that having sad moments doesn't make us sad people, it just makes us people. For those of you who find yourselves in struggle city this time of year, tune in for my advice on how to light the fire under you to get yourself going when you're in a rut, and what to do when you're tired of dating, but not tired of hoping to find love. I answer your voicemails about how to stop being fetishized as an Asian-American woman on dates, and how to cope with your ex moving on and getting engaged to someone else.


Leave me a voicemail: speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2966 How to be yourself in a world that wants you to be like everyone else with Cyrus Veyssi Beauty influencer and TV host Cyrus Veyssi wants us all to know that if a space wasn’t made for you, you can make a space for yourself. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, Cyrus discusses their experience as a non-binary child of immigrants in suburban Boston, why it’s important to understand the difference between someone’s intent versus their impact, and how they use beauty as an act of forgiveness to themselves. We discuss queer dating, why Cyrus prefers to set up straight men and women, and their opinions for how couples should approach money in relationships. If you’ve ever felt limited by the social constructs of gender, sexuality, and identity, this episode is here to remind you that the only right identity is the one that frees you instead of limits you. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Cyrus @cyrusveyssi Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 18 Nov 2024 10:00:00 -0000 How to be yourself in a world that wants you to be like everyone else with Cyrus Veyssi full 6 Anna Kai Beauty influencer and TV host Cyrus Veyssi wants us all to know that if a space wasn’t made for you, you can make a space for yourself. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, Cyrus discusses their experience as a non-binary child of immigrants in suburban Boston, why it’s important to understand the difference between someone’s intent versus their impact, and how they use beauty as an act of forgiveness to themselves. We discuss queer dating, why Cyrus prefers to set up straight men and women, and their opinions for how couples should approach money in relationships. If you’ve ever felt limited by the social constructs of gender, sexuality, and identity, this episode is here to remind you that the only right identity is the one that frees you instead of limits you. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Cyrus @cyrusveyssi Learn more about your ad choices. Visit podcastchoices.com/adchoices Beauty influencer and TV host Cyrus Veyssi wants us all to know that if a space wasn’t made for you, you can make a space for yourself.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


On this week’s episode, Cyrus discusses their experience as a non-binary child of immigrants in suburban Boston, why it’s important to understand the difference between someone’s intent versus their impact, and how they use beauty as an act of forgiveness to themselves.


We discuss queer dating, why Cyrus prefers to set up straight men and women, and their opinions for how couples should approach money in relationships. If you’ve ever felt limited by the social constructs of gender, sexuality, and identity, this episode is here to remind you that the only right identity is the one that frees you instead of limits you.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Cyrus @cyrusveyssi

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]]> 4985 Solo Episode: What to do when everything is falling apart On this week's solo episode, I discuss why sometimes, losing everything you have is the key to getting everything you want. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money If you're wondering how to keep your life together when it appears to insist on falling apart, tune into this episode as we chat about how your "all is lost" moment is not your demise, but your redemption. I dive into the "all is lost" moment in my life that led me to my TikTok career, and why everyone should learn to dine alone. I answer your voicemails on how to determine what a man's intentions are on a date, when you should or shouldn't meet his parents, and how to move on from a man who fell out of love with you. Leave me a voicemail at https://www.speakpipe.com/brutallyannapodcast for me to answer on upcoming episodes. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 14 Nov 2024 10:00:00 -0000 Solo Episode: What to do when everything is falling apart full 6 Anna Kai On this week's solo episode, I discuss why sometimes, losing everything you have is the key to getting everything you want. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money If you're wondering how to keep your life together when it appears to insist on falling apart, tune into this episode as we chat about how your "all is lost" moment is not your demise, but your redemption. I dive into the "all is lost" moment in my life that led me to my TikTok career, and why everyone should learn to dine alone. I answer your voicemails on how to determine what a man's intentions are on a date, when you should or shouldn't meet his parents, and how to move on from a man who fell out of love with you. Leave me a voicemail at https://www.speakpipe.com/brutallyannapodcast for me to answer on upcoming episodes. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices On this week's solo episode, I discuss why sometimes, losing everything you have is the key to getting everything you want.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


If you're wondering how to keep your life together when it appears to insist on falling apart, tune into this episode as we chat about how your "all is lost" moment is not your demise, but your redemption. I dive into the "all is lost" moment in my life that led me to my TikTok career, and why everyone should learn to dine alone. I answer your voicemails on how to determine what a man's intentions are on a date, when you should or shouldn't meet his parents, and how to move on from a man who fell out of love with you.


Leave me a voicemail at https://www.speakpipe.com/brutallyannapodcast for me to answer on upcoming episodes.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

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]]> 3035 You’re not delusional with Serena Kerrigan The queen of confidence, Serena F*cking Kerrigan, wants us all to know that you’re not delulu (*delusional in non-TikTok speak), you just haven’t been taught how to ask for what you want. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, we discuss the importance of listening to your intuition, why Serena believes that we need to emphasize the importance of a woman being confident over a woman being palatable, and why she would never go back to an ex (spoiler: it’s like trying to un-spoil spoiled milk). Using her life as her muse, Serena reminds us all that no one knows what they’re doing, but that the ones who are successful are the ones who dare to try. My conversation with Serena sheds light on how the scarcity mentality implemented by the patriarchy forces women to settle and why you should never be confused in relationships. For anyone who has ever felt like they’ve taken the wrong turn in life, this week’s episode shows us all that sometimes, the wrong turn can lead you to the right destination in the end. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Serena @serenakerrigan Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 11 Nov 2024 10:00:00 -0000 You’re not delusional you just need to learn to ask for and work for what you want with Serena Kerrigan full 5 Anna Kai The queen of confidence, Serena F*cking Kerrigan, wants us all to know that you’re not delulu (*delusional in non-TikTok speak), you just haven’t been taught how to ask for what you want. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, we discuss the importance of listening to your intuition, why Serena believes that we need to emphasize the importance of a woman being confident over a woman being palatable, and why she would never go back to an ex (spoiler: it’s like trying to un-spoil spoiled milk). Using her life as her muse, Serena reminds us all that no one knows what they’re doing, but that the ones who are successful are the ones who dare to try. My conversation with Serena sheds light on how the scarcity mentality implemented by the patriarchy forces women to settle and why you should never be confused in relationships. For anyone who has ever felt like they’ve taken the wrong turn in life, this week’s episode shows us all that sometimes, the wrong turn can lead you to the right destination in the end. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Serena @serenakerrigan Learn more about your ad choices. Visit podcastchoices.com/adchoices The queen of confidence, Serena F*cking Kerrigan, wants us all to know that you’re not delulu (*delusional in non-TikTok speak), you just haven’t been taught how to ask for what you want.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


This week, we discuss the importance of listening to your intuition, why Serena believes that we need to emphasize the importance of a woman being confident over a woman being palatable, and why she would never go back to an ex (spoiler: it’s like trying to un-spoil spoiled milk). Using her life as her muse, Serena reminds us all that no one knows what they’re doing, but that the ones who are successful are the ones who dare to try.


My conversation with Serena sheds light on how the scarcity mentality implemented by the patriarchy forces women to settle and why you should never be confused in relationships. For anyone who has ever felt like they’ve taken the wrong turn in life, this week’s episode shows us all that sometimes, the wrong turn can lead you to the right destination in the end.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Serena @serenakerrigan

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 5254 Solo Episode: The safe man is leading you into dangerous territory On this bonus solo episode, we're diving into why dating apps are the gift wrapping of men and why I'm the not-so-proud owner of no less than a dozen cheese boards. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money Tune in as I unpack the psychology about why gift wrapping influences how much we like the gift itself, how it relates to dating, as well as why sometimes, the safe choice and the safe man isn't actually safe at all. I answer a listener's question about how to handle dealing with the fallout of choosing the wrong man when she was choosing between two men and why we should all look for the squatty potty of a man versus the cheeseboard of a man. You can now leave me voicemails to answer on future episodes here: https://www.speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Thu, 07 Nov 2024 10:00:00 -0000 Solo Episode: The safe man is leading you into dangerous territory full 5 Anna Kai On this bonus solo episode, we're diving into why dating apps are the gift wrapping of men and why I'm the not-so-proud owner of no less than a dozen cheese boards. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money Tune in as I unpack the psychology about why gift wrapping influences how much we like the gift itself, how it relates to dating, as well as why sometimes, the safe choice and the safe man isn't actually safe at all. I answer a listener's question about how to handle dealing with the fallout of choosing the wrong man when she was choosing between two men and why we should all look for the squatty potty of a man versus the cheeseboard of a man. You can now leave me voicemails to answer on future episodes here: https://www.speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices On this bonus solo episode, we're diving into why dating apps are the gift wrapping of men and why I'm the not-so-proud owner of no less than a dozen cheese boards.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


Tune in as I unpack the psychology about why gift wrapping influences how much we like the gift itself, how it relates to dating, as well as why sometimes, the safe choice and the safe man isn't actually safe at all. I answer a listener's question about how to handle dealing with the fallout of choosing the wrong man when she was choosing between two men and why we should all look for the squatty potty of a man versus the cheeseboard of a man.


You can now leave me voicemails to answer on future episodes here: https://www.speakpipe.com/brutallyannapodcast


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 2786 What divorce can teach you about the power of being alone and the rebirthday of Katie Maloney Vanderpump Rules star and entrepreneur Katie Maloney shows us why the path not taken is often the path we’re meant to take. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode Katie details her life as a college dropout, her days before reality TV and VPR, and how she decided that she could only find her best life if she found the courage to end her marriage. We discuss whether she would ever get married again, how she’s found peace as a single thirty-something in L.A., and how she’s no longer willing to be dragged into anyone’s drama, even if it means being alone. For anyone who has felt like their life has, metaphorically, ended, Katie’s story of overcoming a traumatic brain injury and her divorce shows us that there’s no limit, in her words, to the amount of software updates you can have in life.  Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Katie @musickillskate Learn more about your ad choices. Visit podcastchoices.com/adchoices Mon, 04 Nov 2024 10:00:00 -0000 What divorce can teach you about the power of being alone and the rebirthday of Katie Maloney full 4 Anna Kai Vanderpump Rules star and entrepreneur Katie Maloney shows us why the path not taken is often the path we’re meant to take. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode Katie details her life as a college dropout, her days before reality TV and VPR, and how she decided that she could only find her best life if she found the courage to end her marriage. We discuss whether she would ever get married again, how she’s found peace as a single thirty-something in L.A., and how she’s no longer willing to be dragged into anyone’s drama, even if it means being alone. For anyone who has felt like their life has, metaphorically, ended, Katie’s story of overcoming a traumatic brain injury and her divorce shows us that there’s no limit, in her words, to the amount of software updates you can have in life.  Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Katie @musickillskate Learn more about your ad choices. Visit podcastchoices.com/adchoices Vanderpump Rules star and entrepreneur Katie Maloney shows us why the path not taken is often the path we’re meant to take.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


On this week’s episode Katie details her life as a college dropout, her days before reality TV and VPR, and how she decided that she could only find her best life if she found the courage to end her marriage. We discuss whether she would ever get married again, how she’s found peace as a single thirty-something in L.A., and how she’s no longer willing to be dragged into anyone’s drama, even if it means being alone.


For anyone who has felt like their life has, metaphorically, ended, Katie’s story of overcoming a traumatic brain injury and her divorce shows us that there’s no limit, in her words, to the amount of software updates you can have in life. 


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Katie @musickillskate

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4596 The blessing of getting dumped on your birthday with Lindsey Metselaar Lindsey Metselaar, host of the hit dating podcast, We Met At Acme, proves that getting dumped on your birthday can sometimes lead to great things. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, find out why women should listen to what men actually say, why Lindsey believes women are less likely to fall in love at first sight than men, and how the most heartbreaking relationships are sometimes the shortest ones. Lindsey talks about that time she was the other woman, quitting drinking (and other things), and who she thinks cheaters should marry. We unpack her PCOS diagnosis and her fertility journey and how Lindsey navigates her career and her newfound motherhood. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Lindsey @wemetacme Learn more about your ad choices. Visit podcastchoices.com/adchoices Sun, 27 Oct 2024 14:29:00 -0000 The blessing of getting dumped on your birthday with Lindsey Metselaar full 3 Anna Kai Lindsey Metselaar, host of the hit dating podcast, We Met At Acme, proves that getting dumped on your birthday can sometimes lead to great things. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, find out why women should listen to what men actually say, why Lindsey believes women are less likely to fall in love at first sight than men, and how the most heartbreaking relationships are sometimes the shortest ones. Lindsey talks about that time she was the other woman, quitting drinking (and other things), and who she thinks cheaters should marry. We unpack her PCOS diagnosis and her fertility journey and how Lindsey navigates her career and her newfound motherhood. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Lindsey @wemetacme Learn more about your ad choices. Visit podcastchoices.com/adchoices Lindsey Metselaar, host of the hit dating podcast, We Met At Acme, proves that getting dumped on your birthday can sometimes lead to great things.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


On this week’s episode, find out why women should listen to what men actually say, why Lindsey believes women are less likely to fall in love at first sight than men, and how the most heartbreaking relationships are sometimes the shortest ones.


Lindsey talks about that time she was the other woman, quitting drinking (and other things), and who she thinks cheaters should marry. We unpack her PCOS diagnosis and her fertility journey and how Lindsey navigates her career and her newfound motherhood.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Lindsey @wemetacme

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4200 Why you’re attracting all the wrong men and getting over your daddy issues with Violet Benson We’re kicking things off with Violet Benson, host of the podcast Almost Adulting and the brain behind the viral Instagram account @daddyissues_. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this episode, we dive into how Violet managed to break the intergenerational trauma of her upbringing, why she thinks you keep attracting all the wrong men (aka Chads), and whether she really believes that you can meet the right person at the wrong time. Violet dives into her childhood as the daughter of Russian immigrants, the first boy that ever broke her heart, and the active practice of letting go of who you were so you can become who you’re meant to be. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Violet @violetbenson @daddyissues_ @almostadulting Learn more about your ad choices. Visit podcastchoices.com/adchoices Sun, 27 Oct 2024 14:20:00 -0000 Why you’re attracting all the wrong men and getting over your daddy issues with Violet Benson full 2 Anna Kai We’re kicking things off with Violet Benson, host of the podcast Almost Adulting and the brain behind the viral Instagram account @daddyissues_. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this episode, we dive into how Violet managed to break the intergenerational trauma of her upbringing, why she thinks you keep attracting all the wrong men (aka Chads), and whether she really believes that you can meet the right person at the wrong time. Violet dives into her childhood as the daughter of Russian immigrants, the first boy that ever broke her heart, and the active practice of letting go of who you were so you can become who you’re meant to be. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Violet @violetbenson @daddyissues_ @almostadulting Learn more about your ad choices. Visit podcastchoices.com/adchoices We’re kicking things off with Violet Benson, host of the podcast Almost Adulting and the brain behind the viral Instagram account @daddyissues_.


Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money


On this episode, we dive into how Violet managed to break the intergenerational trauma of her upbringing, why she thinks you keep attracting all the wrong men (aka Chads), and whether she really believes that you can meet the right person at the wrong time.


Violet dives into her childhood as the daughter of Russian immigrants, the first boy that ever broke her heart, and the active practice of letting go of who you were so you can become who you’re meant to be.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Follow Violet @violetbenson @daddyissues_ @almostadulting

Learn more about your ad choices. Visit podcastchoices.com/adchoices

]]> 4640 Brutally Anna Trailer Welcome to Brutally Anna, a podcast about finding love, losing love, and all the things we think about a lot, but don’t talk about enough. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money I’m your host, Anna Kai aka maybeboth across social media, here to remind you that life can be beautiful, even when it’s freaking brutal. On this brand new podcast, I’m joined by some of your favorite creators and experts on how they navigate dating, how to stay hopeful when you’ve kissed one-too-many frogs or Chads, and most importantly, how to love yourself when you haven’t yet found someone else to love you. Each week, we tackle everything from dating after divorce, how to ask for what you want from a relationship, and what death can teach us about love and life. If you’ve ever wondered how to begin again when life as you know it has ended, this podcast is here to remind you that the best thing to come out of rejection is often our reinvention. Join me for the premiere of Brutally Anna on October 28th with new episodes on Mondays as I sit down and get you the brutal truth so that you can find your truth. Don’t forget to follow me @maybeboth across social media and subscribe to Brutally Anna wherever you get your podcasts. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Sat, 26 Oct 2024 13:51:00 -0000 Brutally Anna Trailer full 1 Anna Kai Welcome to Brutally Anna, a podcast about finding love, losing love, and all the things we think about a lot, but don’t talk about enough. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money I’m your host, Anna Kai aka maybeboth across social media, here to remind you that life can be beautiful, even when it’s freaking brutal. On this brand new podcast, I’m joined by some of your favorite creators and experts on how they navigate dating, how to stay hopeful when you’ve kissed one-too-many frogs or Chads, and most importantly, how to love yourself when you haven’t yet found someone else to love you. Each week, we tackle everything from dating after divorce, how to ask for what you want from a relationship, and what death can teach us about love and life. If you’ve ever wondered how to begin again when life as you know it has ended, this podcast is here to remind you that the best thing to come out of rejection is often our reinvention. Join me for the premiere of Brutally Anna on October 28th with new episodes on Mondays as I sit down and get you the brutal truth so that you can find your truth. Don’t forget to follow me @maybeboth across social media and subscribe to Brutally Anna wherever you get your podcasts. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices Welcome to Brutally Anna, a podcast about finding love, losing love, and all the things we think about a lot, but don’t talk about enough.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

I’m your host, Anna Kai aka maybeboth across social media, here to remind you that life can be beautiful, even when it’s freaking brutal. On this brand new podcast, I’m joined by some of your favorite creators and experts on how they navigate dating, how to stay hopeful when you’ve kissed one-too-many frogs or Chads, and most importantly, how to love yourself when you haven’t yet found someone else to love you. Each week, we tackle everything from dating after divorce, how to ask for what you want from a relationship, and what death can teach us about love and life.

If you’ve ever wondered how to begin again when life as you know it has ended, this podcast is here to remind you that the best thing to come out of rejection is often our reinvention. Join me for the premiere of Brutally Anna on October 28th with new episodes on Mondays as I sit down and get you the brutal truth so that you can find your truth. Don’t forget to follow me @maybeboth across social media and subscribe to Brutally Anna wherever you get your podcasts.


Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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