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PODCAST

Not Well

Bobby, Jim & Friends

Bobby and Jim have been doing this for seven years and they"re only getting worse. Gay life, American dysfunction, travel chaos, unhinged takes on the news, and conversations that start at foreskin philosophy and end at the collapse of civilization. May cause uncontrolled laughter, sarcasm, and existential dread. You"ve been warned.

comedy comedy interviews

All Episodes

68:11

I Just Realized That I'm Not Even Really Taking the...

Not Well ·

2026/04/03

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. ...

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54:11

The Gooner Algorithm: Squeezing the Sac and Thick Bands

Not Well ·

2026/03/06

Send a textIn 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

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60:19

You got so much attention when you were fatter... Now...

Not Well ·

2026/02/05

Send us a textThis 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

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51:44

You Cannot Send a Silicone Torso Sex Toy to Your...

Not Well ·

2026/01/22

Send us a textThis 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

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53:21

If you’re a boy who wants to play the 'get married'...

Not Well ·

2026/01/08

Send us a textBobby 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

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59:48

You are fisting a cow to get it pregnant. Is that...

Not Well ·

2025/11/21

Send us a texthe 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

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55:24

Face Jobs and Foreskin Philosophy

Not Well ·

2025/11/12

Send us a textThis 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

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50:47

She Had A Condom In Her Vagina For A Week

Not Well ·

2025/10/26

Send us a text 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...

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44:20

It’s our first rapture party. Beam me up, Lorde

Not Well ·

2025/10/05

Send us a textBobby 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

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29:26

How gay is professional wrestling? It’s a soap opera...

Not Well ·

2025/09/18

Send us a textThis 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

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46:47

Imagine wanting a straight best friend who lets you...

Not Well ·

2025/08/31

Send us a textIn this chaotic ride of Not Well, Bobby and Jim spiral from dementia scares and weed brain to childhood slut stories, raw dicks, and armpit fetishes. They argue about stoves, confess about breeding kinks, roast Ron DeSantis’ gay boots, and imagine dying together in an ICU bed. Along the way: Molly gets railed on a park bench, someone admits to jerking off 4 times a day as a teen, and the phrase “double-stuffed slut” is born. By the end, they’re reclaiming faggot, dreaming of pirate

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48:49

Say hi Jimmy boy

Not Well ·

2025/08/02

Send us a textIn this lively episode of 'Not Well,' hosts Bobby and Jimmy Boy dive into a plethora of outrageous and humorous topics. They kick off with a light-hearted banter about their follower Asa and an amusing debate on being known as a 'pillow princess.' The conversation takes unexpected turns as they share their harrowing experience of witnessing a car accident and explore urban hazards. Interspersed with hilarious anecdotes about bar encounters, karaoke, and neighborhood

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60:47

This guy was throat-goating like he was trying to...

Not Well ·

2025/07/19

Send us a textOn this explosive episode of Not Well, Bobby and Jim return after a chaotic two-week hiatus to unpack political incompetence, conspiracy-fueled madness, and downright filthy camp confessions. From government cover-ups and Epstein conspiracies to poolside debauchery and aggressive public dick-sucking, nothing is off-limits. The duo spirals into the absurdity of aging, American dysfunction, Fourth of July dread, and their own questionable behavior at gay campgrounds. With rants about

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37:02

Once a Piece of Food Goes In Your Mouth, It Doesn't...

Not Well ·

2025/06/28

Send us a textIn this episode of Not Well, Bobby and Jim are back and holding nothing back! The guys catch up with some wild stories, from a memorable camping trip that involved a terrifying rainstorm and a surprising racial barrier being broken, to their unfiltered thoughts on Pride weekend, the LGBTQ+ community's hygiene, and a chance encounter with a "Viking" man that has Jim rethinking body hair.Get ready for hilarious and honest conversations as they dive into everything from pee

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59:08

I hope he chokes on an ice cream cone

Not Well ·

2025/05/30

Send us a textJoin Bobby and Jim for another hilariously unfiltered episode of "Not Well". This week, the hosts dive deep into a whirlwind of personal adventures and societal critiques, proving that life is anything but "well". Get ready for candid tales from a cousin's recent wedding, complete with open bars and unexpected "spirals" that led to a guest "not making it". Hear about the hosts' wild night out in Cleveland, featuring casino wins on

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65:34

Your Girl With IBS is Getting Finger Banged in First...

Not Well ·

2025/05/15

Send us a textThis chaotic and hilarious episode of Not Well marks the return of Bobby and Jim after a whirlwind spring that included a trip to Ireland. They catch up on everything from skincare and sugar daddy dreams to bizarre road rage incidents and unhinged homemade driving signs. The centerpiece is their unforgettable Irish adventure—drunken nights in Dublin and Galway, being “cut-shamed” at a gay bar, dealing with horny 20-year-olds, and falling in love with Irish lads, butter, and unbothered

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59:40

Hot Dogs On White Bread Sound Like Something Katy...

Not Well ·

2025/04/25

Send us a textIn this chaotic pre-vacation catch-up, Bobby and Jim return after a brief hiatus to unpack their lives before jetting off to Ireland. From skincare obsessions and Spirit Airlines horror stories to hot dentist encounters and the psychology behind sounding "too gay," the duo dives headfirst into everything. They rant about billionaires in space (screw you, Katy Perry), the illusion of economic wins, and the prison industrial complex. There’s also a heartfelt moment reflecting

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54:34

I’m not good at spitting, but I’m great at throwing up.

Not Well ·

2025/04/04

Send us a textIn this unedited chaos-core episode of Not Well, Bobby and Jim dive into hot mess territory with unfiltered rants about April Fools’ trauma, she-cocks, the “goon” community, straight men in denial, crying influencers, and the dream of a five-man Irish rugby orgy. Between travel anxieties and poop logistics on planes, they still find time to manifest fame, mock chemsex culture, and debate why lesbians are society’s most helpful gays.Support the showAs always you can write us at

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60:04

Can I take this medicine orally or anally? You decide

Not Well ·

2025/03/27

Send us a textIn this outrageously entertaining episode of the "Not Well" podcast, hosts Bobby and Jim deliver a rollercoaster of laughter, shock, and unfiltered banter. Tune in as they explore Jim's wild travel escapades through Amsterdam's infamous red-light district, sharing eye-popping encounters involving explicit peep-show booths, quirky condom stores with flamingo-shaped protection, and surreal canal rides filled with unexpected comedy.They hilariously recount personal

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59:01

I got milked by my own shit!

Not Well ·

2025/03/13

Send us a textIn this chaotic and hilarious episode of Not Well, Bobby and Jim dive into a variety of topics ranging from reality TV and cult conspiracies to open relationships and political absurdities. They kick things off with a Chris Lilley reference before discussing the eerie themes of Severance, the state of weight loss drugs like Zepbound, and their upcoming trip to Ireland.They also explore their thoughts on open relationships, the ridiculousness of transphobic sports policies, and the

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299 results

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