Tripping on Kay

Dad pitches Ben his new startup (it's DoorDash, but worse), Grant Claytor crashes the episode, we find out what LARPing is, and the penalty for breaking the rules is a dog treat. Somebody eats it.

David has a ChatGPT history. Ben has questions. Nobody is leaving this conversation with their dignity intact. On this episode of **Tripping on Kay**, we investigate David’s increasingly questionable ChatGPT searches, debate whether he should be allowed to use technology unsupervised, and somehow end up discussing everything from birthday messages and awkward personal questions to facial symmetry...

David has a lot to say. The problem? He has absolutely no idea how to tell a story. This week on **Tripping on Kay**, Ben starts rating David’s storytelling out of 10—and the reviews are brutal. From questionable childhood stories and a game of word association that goes completely off the rails to a possible tattoo and an argument over a missed birthday text, the conversation somehow gets more ch...

Cousin Greg finally joins Tripping on Kay, and somehow David manages to make a family reunion feel like a public relations disaster. This episode has surprise guests, a disastrous doctor phone call, a blindfolded guessing game, questionable jokes, and a deep dive into whether David is actually racist—or just says things he probably shouldn't say out loud. Greg shares stories about growing up aroun...

David and Ben are back on Tripping on Kay, and this episode might officially be their most chaotic one yet. It starts with black coffee, white pants, a missing bubble-machine battery, a hungover Ben, a purple bird, and a debate over whether The Doors actually suck. Then David spends half the episode desperately waiting for his doctor to call while repeatedly losing his train of thought, forgetting...

David and Ben are back on Tripping on Kay, and somehow this episode goes from cake pops, eye patches, Shaky Knees, parrot accessories, penis disappearing into the body, and some truly terrible “would you rather” questions… to one of the most honest conversations they’ve had about MS. David opens up about what it actually feels like living with multiple sclerosis — the pain, the constant discomfort...

Things got out of hand FAST on this episode of Trippin' on Kay. We started off blindfolded touching random objects, but it quickly devolved into calling out Dad's extremely questionable "jokes" and trying to figure out if he's actually offensive or just wildly out of touch. Add in Temu shopping addictions, stand-up comedy pipe dreams, and a morality test where people might die for a briefcase of c...

David and Benjamin are back for another completely unfiltered episode of Tripping On Kay! This week, David takes father-son conversations to a new low with the story of his peppermint oil urinal disaster. From debating whether David should start smoking cigars again despite doctor warnings, to analyzing Ben’s TIE-fighter gagging noises and playing a game of isolated-track music trivia, this episod...

Producer, mixer, and total genius Alex Poeppel joins David and Ben on this week’s episode of Trippin On! Things get off the rails almost immediately as David tests Alex’s boundaries with outlandish hypothetical questions, bizarre circumcision urban legends, and chaotic family stories. From debates about The Office and 4chan to a very specific "Would You Rather" scenario that leaves everyone questi...

David, Ben, and Cheryl are back on **Tripping on Kay** for another episode of what David calls “Family Therapy.” This time, Ben and his dad get into an argument about what it actually means to be a grown-ass adult, while Cheryl sits between them trying to make sense of both of them. Somehow, that turns into a 20-minute debate about whether it’s gross to double-dip your own French fry, whether mail...

On this episode of Tripping on Kay, David and Ben take on a chaotic game of Mind Meld with producer Ian, resulting in unexpected answers and hilarious mismatches. The duo dives into David’s obsession with ChatGPT, debates ELA vocabulary words, breaks down family memories and dark humor trivia, and navigates David's colorblindness with a series of visual tests. Timestamps / Key Moments: 00:00 – Out...

On this episode of Tripping on Kay, David and Ben dive into total chaos—from customized water bottle prank stickers and re-adjusting podcast chairs to eBay reselling wins (and losses). David breaks down his latest online sales strategy, Ben questions his dad’s logic at every turn, and the two debate music trivia, family habits, and why living together leads to non-stop banter. Timestamps / Key Mom...

David and Ben are back on Tripping on Kay for another father-son episode that starts with David being tired, cranky, and worried about spilling coffee — so naturally, it becomes one of the most chaotic episodes yet. This week, David tries to figure out angel numbers, interrogates Zan about being Pakistani, confuses Malaysia with malaria, talks about CPAP problems, tongue sandwiches, Wawa pretzels,...

David and Ben are back on Tripping on Kay for another father-son episode that starts with Sublime, pretzels, riggers, bubbles, and David trying to remember everything he wanted to say. This week, Ben talks about working a music festival and getting his family side stage for Sublime, while David somehow turns the whole thing into a complaint about not getting a giant pretzel. From there, they spira...

David and Ben are back on Tripping on Kay for another father-son episode that starts with David upset about his wheelchair and quickly turns into one of their most honest conversations yet. This week, David opens up about MS, losing independence, not being able to do the simple things he used to do, and what it feels like to go from working nonstop to waking up every day in a hospital bed in the l...

David and Ben are back on **Tripping on Kay** for another father-son episode where David shows up ready for his big News 12 moment… only for the news to cancel on him again. From there, things go exactly where they always go: nowhere and everywhere at the same time. This week, David asks for a laugh track, explains why he wore “normal pants,” revisits the wombat story, talks about his wheelchair u...

Talia joins Tripping on Kay and David immediately realizes this may have been a very bad idea. After multiple episodes of David talking about her, Talia finally sits down with Ben, David, and Pat to confront the chaos directly. They talk about her first impression of David, her relationship with Pat, dating, attraction, Jewish families, OnlyFans jokes, David’s disability, MS, cancer, tattoos, exte...

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 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, tha...

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...

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 whethe...

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 fa...

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 hi...

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. Welc...

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’...