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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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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 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

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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.

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