Tripping on Kay

My Dad Got Lost In Manhattan… - Episode 14 - Tripping on Kay

Tue, 07 Jul 2026 21:00:00 -0000

David and Ben are back on Tripping on Kay for another father-son episode that starts with David getting lost in Manhattan, nearly killing his wheelchair battery, hiding out in a bagel store, and somehow arriving with a story that takes way too long to tell.

From there, things only get more chaotic.

This week, David eats a dog treat on camera, Ben talks about turning 27 and going all in on his art, David shares his excitement about a new wheelchair and a News 12 interview, and the two get into a real conversation about first impressions, family, caregiving, embarrassment, and why their dynamic makes Ben feel like he looks mean.

It’s gross, honest, ridiculous, emotional, and exactly what happens when David is left alone in New York City for too long.

Welcome to Tripping on Kay.

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Instagram: https://www.instagram.com/trippingonkay/
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YouTube: https://www.youtube.com/@trippingonkay
Spotify: https://open.spotify.com/show/4SPex0kN0cUQ7Dn9fupwUo?si=04dd1af6106444e1
Apple Podcasts: https://podcasts.apple.com/us/podcast/tripping-on-kay/id1889667024
Patreon: https://www.patreon.com/cw/TrippingonKay

#podcast #comedy #fatherandson #trippingonkay #comedypodcast

Dad Needs A Disclaimer - Episode 13 - Tripping on Kay

Tue, 30 Jun 2026 21:00:00 -0000

David and Ben are back on Tripping on Kay for another father-son episode where David promises he’s going to stay calm, not squirrel, not insult anyone, and actually listen.

Naturally, that lasts about thirty seconds.

This week, David gives himself a pep talk, Ben admits he’s been in a mood, and the two talk about the “three H’s”: whether someone needs a hug, help, or just to be heard. Somehow, that turns into Soul Brew, stand-up comedy, awkward jokes, dead-or-alive dinner guests, family, grief, Frank Ocean, Uncle Howie, nursing home memories, food carts, Ian vs Pat, and David panicking over a five-minute warning.

It’s chaotic, funny, weirdly honest, and another father-son conversation that probably needed a disclaimer.

Welcome to Tripping on Kay.

#podcast #comedy #fatherandson #trippingonkay #comedypodcast

I Made My Dad Take A Narcissism Test… - Episode 12 - Tripping on Kay

Tue, 23 Jun 2026 21:00:00 -0000

David and Ben are back on Tripping on Kay for another father-son episode that starts with Amish buggy reflectors and somehow turns into a full narcissism test.

This week, David tries to stay on track, Ben tries to keep the show from spiraling, and the two end up talking about Pat’s girlfriend, Jessica’s episode, memory problems, migraines, medication, Ben shaving his head, new life chapters, Harry Potter, grammar, Patreon tiers, and whether David might actually be a narcissist.

It’s chaotic, uncomfortable, weirdly honest, and exactly why this podcast works.

Welcome to Tripping on Kay.

#podcast #comedy #fatherandson #trippingonkay #comedypodcast

Jessica Levin Was Not Ready For My Dad… - Episode 11 - Tripping on Kay

Tue, 16 Jun 2026 21:00:00 -0000

Jessica Levin joins Tripping on Kay and immediately gets thrown into the universe.

This episode has everything:

David trying to explain himself,

Ben trying to keep the show alive,

Jessica roasting both of them,

“crabs” getting introduced as the official truth test,

and a conversation that somehow jumps from dating, music, would-you-rathers, Jewish identity, Wawa pretzels, rehab stories, and whether David is actually one Fruit Loop in a bowl of Cheerios.

Jessica didn’t just survive the chaos — she kept up.

Welcome to Tripping on Kay.

#podcast #comedy #fatherandson #trippingonkay #comedypodcast

Buckle Up! - Episode 10 - Tripping on Kay

Tue, 09 Jun 2026 21:00:00 -0000

Welcome back to Tripping on Kay.

This week, my dad says “buckle up” and immediately proves why he needs a disclaimer before every episode.

We talk about Manhattan, identity, Gen Z slang, affirmations, MS, family, caretaking, and why every serious conversation somehow turns into something we probably shouldn’t say out loud.

It’s inappropriate, emotional, chaotic, and weirdly honest.

Just another father-son conversation where nobody knows where it’s going.

Especially us.

Like, comment, subscribe, and buckle up.

#podcast #fatherandson #comedy #realtalk #trippingonk

My Dad Has Been Researching Wheelchair Mods For 5 Hours. - Episode 9 - Tripping on Kay

Wed, 03 Jun 2026 04:21:00 -0000

In this episode of Tripping on Kay, my dad and I go from discussing his MS treatment and insurance battles to talking about success, family, bucket lists, and what the future might actually look like.

We talk about:

Multiple sclerosis and navigating healthcare
My dreams as an artist
Whether success changes people
Bucket-list goals
Why my dad thinks I might become famous and forget about him
And his latest obsession: turning his wheelchair into a bubble-powered custom ride

Somehow serious.
Somehow ridiculous.
Exactly what you'd expect from us.

Welcome to Tripping on Kay.

ft. Emma Willmann - Episode 8 - Tripping on Kay

Tue, 26 May 2026 21:00:00 -0000

This episode went completely off the rails.

A famous comedian joined me and my dad for one of the most chaotic conversations we’ve had yet — and somehow we ended up talking about:

family code words lies you can never take back

ADHD

relationships

disease childhood stories

and things that absolutely should not have been said on camera

Somehow emotional. Somehow inappropriate. Somehow hilarious.

Welcome to Tripping on Kay.

#podcast #comedy #fatherandson #realtalk #comedypodcast

Dad vs. Best Friend! - Episode 7 - Tripping on Kay

Tue, 19 May 2026 21:00:00 -0000

This episode got chaotic fast…

I brought my best friend on the podcast with my dad, and somehow it turned into:

A debate about whether your parent should be your best friend
My dad admitting he secretly watched me without me knowing
My best friend taking my dad’s side more than mine
Wild stories from our past (and things that probably shouldn’t have been said)

It’s 2 vs 1, it’s unfiltered, and it’s real.

Welcome to Tripping on Kay.

#podcast #friendship #family #realtalk #comedy

My Dad Asked Me To Be His Life Coach… - Episode 6 - Tripping on Kay

Tue, 12 May 2026 21:00:00 -0000

This episode started as a normal conversation… and turned into something way more real. We talked about: * Why I’m so hard on my dad * The truth about trying to help family change * Our dynamic off-camera vs on-camera * And the line between love, frustration, and honesty It’s funny, it’s chaotic, but this one hits different. This is what real conversations look like. Welcome to Tripping on Kay. #podcast #family #realtalk #fatherandson #comedy

FAMILY THERAPY - Episode 5 - Tripping on Kay

Tue, 05 May 2026 21:00:00 -0000

This might be our most unfiltered episode yet.

We brought my mom onto the podcast… and somehow it turned into:

My parents exposing how they actually met
Wild stories we’ve NEVER talked about
Childhood moments I didn’t even remember
And conversations that probably should’ve stayed off camera

It’s chaotic, it’s inappropriate, and somehow still real.

This is what happens when you put a family like ours behind microphones.

Welcome to the madness.

#podcast #family #comedy #unfiltered #realtalk

Am I Too Much to Handle? - Episode 4 - Tripping on Kay

Tue, 28 Apr 2026 21:00:00 -0000

This episode of Tripping on Kay starts off like any other…

but turns into one of the most honest conversations we’ve had.

What begins as jokes and random chaos slowly shifts into something deeper—talking about what it’s actually like living with each other, dealing with change, and being honest even when it hurts.

We talk about:

What it’s like being a father and son in real life
Living with MS and how it affects everything
Feeling like “too much” for the people around you
And saying things you don’t really want to hear

It’s uncomfortable.
It’s real.
And it’s probably something most people don’t talk about out loud.

If you’ve ever wondered how people really feel about you… this one hits.

We’re Definitely Getting Cancelled Again… (ft. Grant Claytor) - Episode 3 - Tripping on Kay

Tue, 21 Apr 2026 21:00:00 -0000

This episode of Tripping on Kay might be the one that gets us banned again…

We bring in a guest—and immediately lose control.

From completely unfiltered jokes to conversations that probably shouldn’t be on camera, this episode pushes every boundary we’ve already been warned about.

But underneath the chaos, there’s something real:
trying to figure out what you’re actually allowed to say… and why it even matters.

We talk about:

Getting banned (multiple times) and why
Saying the wrong thing vs saying what you actually think
The line between funny and “too far”
And why this podcast refuses to filter itself

It’s reckless.
It’s uncomfortable.
And it’s probably a bad idea.

But it’s real.

We Argued Over a Spoon… Then It Got Real - Episode 2 - Tripping on Kay

Tue, 14 Apr 2026 21:00:00 -0000

This episode of Tripping on Kay starts with one of the dumbest arguments we’ve ever had…

over a spoon.

But what starts as petty frustration quickly turns into something deeper—talking about validation, success, ego, and why we see the world completely differently.

From ridiculous moments to real tension, this is what happens when a father and son don’t filter anything.

We talk about:

Why small things turn into big arguments
The need for validation vs not caring at all
What success actually means
And why this dynamic works… even when it doesn’t

It’s chaotic.
It’s uncomfortable.
But it’s real.

If you’ve ever argued over something stupid… and realized it wasn’t actually about that thing—this episode is for you.

A father and son argue over something stupid… then end up talking about validation, ego, and what actually matters.

This Podcast Got Too Real… (We Almost Didn’t Come Back) - Episode 1 - Tripping on Kay

Tue, 07 Apr 2026 21:00:00 -0000

This episode of Tripping on Kay starts off completely unhinged…
and somehow turns into something real.

From fart noises and inappropriate jokes to brutally honest moments about life, illness, and losing control—this is what happens when a father and son stop filtering themselves.

We talk about:

Life changing overnight
Living with MS and how it actually feels
Using humor to cope with things you can’t fix
And why this podcast almost didn’t come back

It’s chaotic.
It’s offensive.
But underneath it… it’s real.

If you’ve ever laughed through something you were actually struggling with—this one’s for you.

A father and son go from completely unfiltered chaos to real conversations about illness, life changes, and why humor becomes survival.