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by Bobby, Jim & Friends
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Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 2 weeks ago57 min
Most Pretty Dicks Are On Ugly Faces
Send us Fan Mail Episode 299 of Not Well Podcast is complete disorder. This week Bobby and Jim discuss drinking out of the sink, gay nightlife chaos, furry encounters, hookup apps, Italy travel plans, weird kinks, hot people problems, armpit attraction science, toxic cookware paranoia, seat-switching airplane drama, and why some people stir coffee for far too long. Comedy, zero filter, questionable logic, and premium nonsense. Subscribe, rate, review, and send in your own “Not Well” stories. ...
- 3 weeks ago55 min
Wait… You Can’t Botox Your Knees?
Send us Fan Mail Episode 298 of Not Well Podcast is chaos in its purest form. This week Bobby and Jim spiral through aging panic, weird beauty standards, Botox limits, golf bros, gay bar behavior, bald head hotness, awkward encounters, body image, nightlife nonsense, and the random observations nobody else is brave enough to say out loud. Sharp humor, zero filter, and two hosts trying to stay semi-functional. Subscribe, leave a review, and send in your own “Not Well” stories. Support the show...
- Apr 17, 20261h 5m
Wait, You Don't Trim an Abandoned Lawn?
Send us Fan Mail This week on Not Well, Bobby and Jim spiral beautifully through a night out that started with cheap margaritas and ended somewhere between gay bar chaos, moon conspiracies, death talk, body shame trauma, and the collapse of modern society. We cover: A wild night at Lupitas and Columbus bars Meeting a hot casket salesman Why American car culture is broken Weird truths about body odor and shame Going around the moon… again? ...
- Apr 3, 20261h 8m
I Just Realized That I'm Not Even Really Taking the Medication the Way I Should Be
Send us Fan Mail We finally made it to Dallas, and let’s just say the Big D stood for more than just the city name. In this episode, we’re peeling back the foil on our own incompetence—specifically how we’ve been winging our medical prescriptions while trying to maintain a 10/10 aesthetic. We’re diving into the "Modern Grime" of our travel habits, from the "Cornhole Lesbians" of Texas to the absolute panic of a self-driving car that almost ended it all before we even reached the hotel. ...
- Mar 6, 202654 min
The Gooner Algorithm: Squeezing the Sac and Thick Bands
Send us Fan Mail In this unfiltered catch-up, Bobby and Jim dive into a chaotic month of travel, awkward social encounters, and the strangest corners of the internet. From the "scenes" in Puerto Vallarta and Cleveland to the frustrations of being blocked on dating apps in Columbus, no topic is off-limits. We explore the "profound" world of energy work and chakras after a life-altering massage, share our anxieties about aging and health, and somehow end up deep in the rabbit hole of Reborn Dol...
- Feb 5, 20261h 0m
You got so much attention when you were fatter... Now we walk in and we're just old
Send us Fan Mail This episode of "Not Well" is a brutally honest, stream-of-consciousness conversation about navigating gay life in your 30s with all its contradictions and anxieties. The hosts dive deep into the psychological aftermath of major weight loss, discussing how losing 65-70 pounds has paradoxically made one of them feel less attractive in gay spaces—getting way more attention as a bigger bear than as a slimmer guy. They question whether it's the weight, aging, or just a combinatio...
- Jan 22, 202651 min
You Cannot Send a Silicone Torso Sex Toy to Your Mother’s House.
Send us Fan Mail This episode starts where all good family stories end: with a silicone torso sex toy accidentally delivered to a mother’s house. From there, Bobby and Jim spiral through modern shame, bad decisions, creative vulnerability, and the unspoken rules everyone knows but nobody says out loud. They talk about incoherent politics, Irish gin, finishing a deeply personal short film, aging out of nightlife, and why “discreet” hookups are never discreet. Along the way: • a hor...
- Jan 8, 202653 min
If you’re a boy who wants to play the 'get married' game [as a child], you’re gay. Bottom. You want to be the bride.
Send us Fan Mail Bobby returns from his "Echoes Abroad" tour of Ireland and Copenhagen with a a questionable "director lesbian" aesthetic. While Bobby recounts the struggles of finding a decent sunrise in Dublin and the perils of feeling "famous" on TikTok, Jim, who has had flu, shares a horrifying domestic scene involving nose hair plucking and corns. The boys pivot to heavier topics—literally—discussing dead bodies at viewings, before Bobby drops a bombshell story about a massage that got a...
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About Not Well
Join Bobby and Jim on 'Not Well', where fearless conversations meet humor and wisdom in an explosion of topics ranging from the latest celebrity gossip to the intricacies of gay issues and politics. With Bobby's unconventional wisdom, often fueled by his adventures with edibles, leading us into the most random and taboo subjects you'd never dare to bring up, and Jim's sharp intellect providing insightful commentary, there's never a dull moment.Our podcast is a bold, inclusive space that welcomes gay men, straight women, and straight men alike, especially those who are curious about a wide array of discussions—including the candid exploration of sex and men's bodies. Bobby and Jim create a safe haven for laughter, connection, and sometimes the outright bizarre, ensuring our listeners feel happy, engaged, and part of a larger community.Every Thursday we dive deep into everything under the sun, from the most controversial topics to the day-to-day quirks of
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