Not Well | A Comedy Podcast

Bobby, Jim & Friends

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 life. Our unique content mix, featuring listener voicemails and the funniest Tik Toks, complements our discussions, making 'Not Well' more than just a podcast—it's a movement towards embracing our not-so-perfect selves. Subscribe now and join our community where being 'not well' is celebrated, and discovering the joy in life's randomness is a weekly adventure. Experience the dynamic duo of Bobby's wild tangents and Jim's smart insights, and see why our listeners can't get enough of our unapologetic take on the world.

  1. The Gooner Algorithm: Squeezing the Sac and Thick Bands

    MAR 6

    The Gooner Algorithm: Squeezing the Sac and Thick Bands

    Send a text 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 Dolls and Gooning subcultures. Plus, we discuss why "prices are down" at Costco and critique the latest in A24-style cinema. [00:00] Travel Recaps: New York, Atlanta, and Puerto Vallarta[12:15] Dating App Disasters: Why am I getting blocked?[24:30] Cinema & Pop Culture: Taylor Swift, Charli XCX, and "The Moment"[38:45] Wellness & Energy: The Chakra-Opening Massage[52:20] Aging Anxieties: Physical health and the fear of the unknown[1:05:10] Internet Subcultures: Exploring the world of Reborn Dolls[1:18:40] The Gooner Algorithm & "Bating" CultureSupport the show As always you can write us at nowellpodcast@gmail.com or call us at ‪(614) 721-5336‬ and tell us your Not Wells of the week Instagram Twitter Bobby's Only Fans Help us continue to grow and create amazing content, like a live tour or just help fund some new headphones when needed. Any help is appreacited. https://www.buzzsprout.com/510487/subscribe #gaypodcast #podcast #gay #lgbtq #queerpodcast #lgbt #lgbtpodcast #lgbtqpodcast #gaypodcaster #queer#instagay #podcasts #podcasting #gaylife #pride #lesbian #bhfyp #gaycomedy #comedypodcast #comedy #nyc #614 #shesnotdoingsowell #wiltonmanor #notwell

    54 min
  2. FEB 5

    You got so much attention when you were fatter... Now we walk in and we're just old

    Send a text 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 combination of everything that's changed the dynamic when walking into bars. The conversation spirals through modern absurdities: how delusional confidence seems to be the key to success (citing the Hawk Tuah girl making $15 million), generational differences in handling internet fame, and why their generation can't just embrace the chaos like younger people do. They touch on practical frustrations like airplane etiquette—specifically calling out first-class passengers who put backpacks in overhead bins—and the hilarious reality that TSA agents will move weed gummies aside to check electronics. The episode gets vulnerable discussing body dysmorphia, balding, potential thyroid issues, and the complex relationship with hookup culture. One host reveals he actually needs emotional connection before sex and hates the idea of planned "sex dates," despite being perfectly fine with spontaneous bathroom encounters or random basement hookups. It's a fascinating contradiction that speaks to the difference between performative sexuality and genuine desire. Throughout, there's constant self-awareness about their modest podcast success (hundreds of listeners, not thousands), frustration with social media narcissism, and the ongoing struggle to stay motivated during cold weather. The tone is profane, self-deprecating, and refreshingly authentic—two friends processing their lives out loud without filter. Support the show As always you can write us at nowellpodcast@gmail.com or call us at ‪(614) 721-5336‬ and tell us your Not Wells of the week Instagram Twitter Bobby's Only Fans Help us continue to grow and create amazing content, like a live tour or just help fund some new headphones when needed. Any help is appreacited. https://www.buzzsprout.com/510487/subscribe #gaypodcast #podcast #gay #lgbtq #queerpodcast #lgbt #lgbtpodcast #lgbtqpodcast #gaypodcaster #queer#instagay #podcasts #podcasting #gaylife #pride #lesbian #bhfyp #gaycomedy #comedypodcast #comedy #nyc #614 #shesnotdoingsowell #wiltonmanor #notwell

    1 hr
  3. You Cannot Send a Silicone Torso Sex Toy to Your Mother’s House.

    JAN 22

    You Cannot Send a Silicone Torso Sex Toy to Your Mother’s House.

    Send a text 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 horrifying holiday package mix-up  • the psychological damage of Amazon Prime  • why bars feel younger, emptier, and louder  • the fear of being seen when the camera turns on you  • and the hard truth that some packages should never be opened It’s uncomfortable. It’s funny. It’s too honest.  In other words: Not Well. Support the show As always you can write us at nowellpodcast@gmail.com or call us at ‪(614) 721-5336‬ and tell us your Not Wells of the week Instagram Twitter Bobby's Only Fans Help us continue to grow and create amazing content, like a live tour or just help fund some new headphones when needed. Any help is appreacited. https://www.buzzsprout.com/510487/subscribe #gaypodcast #podcast #gay #lgbtq #queerpodcast #lgbt #lgbtpodcast #lgbtqpodcast #gaypodcaster #queer#instagay #podcasts #podcasting #gaylife #pride #lesbian #bhfyp #gaycomedy #comedypodcast #comedy #nyc #614 #shesnotdoingsowell #wiltonmanor #notwell

    52 min
  4. 11/21/2025

    You are fisting a cow to get it pregnant. Is that what God wants?

    Send a text he conversation moves through a fast, chaotic blend of social commentary, sexual humor, political cynicism, and personal reflection. It begins with discussion about the resurgence of collectible items and how AI and capitalism may force people back into simpler, more human activities. That leads into a critique of money, crypto, billionaires, and the concept that nearly everything in modern society is essentially fake. The dialogue expands into global politics—sanctions, coups, oil interests, and the U.S. acting as an unchecked global power. From there, the tone shifts into absurd humor about farming, insemination, and how people who fist cows often hold conservative anti-LGBT views. The conversation spirals into kink culture: leather scenes, pups, masks, fetishes, and why certain communities exist. This includes uncomfortable, explicit questions about fisting, bodily functions, sexual progression, and why some people enjoy extreme acts. The discussion then swerves to everyday life: talking to dogs like children, dogs’ pack behavior, the contrast with aloof cats, and the bizarre reality of pets living indoors. Food prices, inflation, and the shrinking size of groceries become a point of frustration. The conversation returns to personal growth, aging, creative phases, past podcast eras, and how both hosts have changed since earlier episodes. Nostalgia for past creative periods emerges, along with recognition of personal evolution. Interwoven is a thread about filmmaking: the beginning of a documentary project, motivations behind solo travel, the meta-process of documenting the making of a documentary, and how it ties to self-reflection. The dialogue continues into aging, nightlife shifting into quiet routines, and the strange dissonance between adult responsibilities and the outrageous conversations they still have. Overall, the transcript jumps from existential dread to explicit gay sexual comedy, from geopolitical collapse to pet parenting, from leather festivals to the price of soup—all narrated with unfiltered honesty, sarcasm, and vulgar humor. Support the show As always you can write us at nowellpodcast@gmail.com or call us at ‪(614) 721-5336‬ and tell us your Not Wells of the week Instagram Twitter Bobby's Only Fans Help us continue to grow and create amazing content, like a live tour or just help fund some new headphones when needed. Any help is appreacited. https://www.buzzsprout.com/510487/subscribe #gaypodcast #podcast #gay #lgbtq #queerpodcast #lgbt #lgbtpodcast #lgbtqpodcast #gaypodcaster #queer#instagay #podcasts #podcasting #gaylife #pride #lesbian #bhfyp #gaycomedy #comedypodcast #comedy #nyc #614 #shesnotdoingsowell #wiltonmanor #notwell

    1 hr

Trailer

4.6
out of 5
86 Ratings

About

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 life. Our unique content mix, featuring listener voicemails and the funniest Tik Toks, complements our discussions, making 'Not Well' more than just a podcast—it's a movement towards embracing our not-so-perfect selves. Subscribe now and join our community where being 'not well' is celebrated, and discovering the joy in life's randomness is a weekly adventure. Experience the dynamic duo of Bobby's wild tangents and Jim's smart insights, and see why our listeners can't get enough of our unapologetic take on the world.

You Might Also Like