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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.

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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.

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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 little too close for comfort (and anatomy). Plus, the duo debates the aesthetics of white underwear, the "marriage game" as a litmus test for being a bottom, and the sheer size of Irish heads.

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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.

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This Not Well episode is chaotic, funny, and wildly inappropriate in true Bobby-and-Jim fashion. It bounces from self-deprecating body talk and aging jokes to dark humor about ancestry, suicide, and religion—before spiraling into AI obsession, first-class flight hacks, uncut dick curiosity, fungal infections, and political outrage. The second half dives into everything from dementia couples and priest trauma to SNAP benefits, U.S. corruption, and gay community hypocrisy, closing with drunk theater reviews and existential crises. It’s part therapy session, part stand-up set, and entirely unfiltered.

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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

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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

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Bobby's Only Fans

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Bobby and Jim return after a chaotic few weeks with an unfiltered, hilarious deep dive into the apocalypse, neighborhood drama, and America’s collective psychosis. From “RaptureTok” lunatics leaving their clothes out for Jesus to MAGA cults worshiping the golden calf, nothing is off limits. The boys spiral through religion, politics, tailgating chaos, and dog poop wars on their street—all while high, ranting, and trying not to get arrested. It’s equal parts stand-up, meltdown, and sermon for the end times.

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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

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This episode of Not Well is chaotic, funny, and raw—Bobby and Jim dive into everything from soccer games and drag shows to conspiracy theories and neighborhood drama. It kicks off with banter about attending a USA vs. Japan match and Bobby’s struggle with overstimulation in large crowds. They move into cultural commentary: Japan’s heat, high-speed trains vs. America’s broken transit, and the hypocrisy of U.S. politics around alcohol, weed, and guns.

From there, the conversation spirals through:

The Trump/Epstein files controversy and censorship.

Weird political alignments (liking Marjorie Taylor Greene tweets “against their will”).

The broken state of America and the absurdity of “jobs just to keep jobs.”

A disastrous drag show at Kemba, drinking mishaps, and weight-loss meds.

Jazz nights at an LGBTQ-friendly church, with a white singer butchering Brazilian lyrics.

A breakdown of “stan culture,” Eminem’s Stan, and K-pop superfans.

The gay undertones of wrestling and male friendships disguised as “bromance.”

A neighbor feud escalating into harassment notes and police calls.

Random sundries: hating Indian summers, wanting hoodie weather, planning trips, art frustrations, and Bobby admitting Penis Friends might be losing steam.

The episode closes with a mix of edible-fueled rambling, travel talk (Mexico, Ireland), crafts, and a GoPro request for scuba diving.

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

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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