Not Well | A Comedy Podcast

Not Well | A Comedy Podcast

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.

Episodes

November 21, 2025 59 mins

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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...

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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 b...

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October 26, 2025 50 mins

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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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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 tryi...

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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...

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In 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-stu...
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August 2, 2025 48 mins

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In 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 wit...

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On 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 the...

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In 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 fo...

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Join 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 ho...

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This 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-ye...

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In 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 pr...

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In 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 mos...

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In 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 ride...

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March 13, 2025 59 mins

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In 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 relations...

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March 6, 2025 68 mins

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This episode dives into a chaotic mix of topics, kicking off with an absurd discussion about government spending on transgender mice before spiraling into an existential rant about sleep routines. The struggle of putting in a mouthguard, earplugs, and taking melatonin like a nightly pre-flight checklist is real, and the resentment toward winter laziness is reaching peak levels.

Travel plans are a big theme, with talk o...

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This episode was a whirlwind of chaotic energy fueled by cold brew, deep thoughts on dicks, and unsolicited introspection. Bobby and Jim discuss everything from waking up at ungodly hours, Botox touch-ups, and the undeniable power of bulge bands. There’s talk of mysterious Irishmen, deep-seated bisexuality panic, and how Gen Z is dismantling the big dick industrial complex. The boys take a detour into a philosophical ...

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February 5, 2025 67 mins

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The episode begins with a chaotic, rapid-fire discussion on current events, conspiracy theories, and pop culture, blending humor, absurdity, and deep frustration over political affairs. The hosts open with an explosive claim that the federal government is experiencing a private takeover under the guise of reform, referencing missing CDC datasets and security concerns with high-ranking officials using Gmail.

The convers...

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This chaotic episode covers everything from personal health woes to existential dread, with plenty of political rants and inappropriate humor in between. The hosts, overtired and slightly sick, spiral through absurd conversations about bodily functions, credit scores, and the downfall of America.

Main Topics Discussed:

  • Energy Struggles & Gum Chewing – Trying to wake up, chewing gum aggressively for theanine, and...
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This episode of Not Well dives deep into chaotic and hilarious conversations ranging from Trumpism, trans rights, societal failings, crumbs, childhood fears, and a lot of irreverent humor. Bobby and Jim dissect the ridiculousness of patriotism displayed during inaugurations, the bizarre cult-like worship of certain political figures, and the ongoing culture war surrounding trans individuals. They reminisce about their...

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