Talking to a Flirty AI?! | If This Doesn’t Work… Ep. 81 21.07.2025 1:21:08

Ever talked to an AI that flirts with you? In this episode of If This Doesn’t Work… , we go completely off the rails. We start by reading hilarious (and brutal) comments from our viral 607 Unc episode, dive into a deep rant about pet ownership, trauma, and parenting styles… and then end up having a wild, slightly disturbing conversation with Elon Musk’s Grok AI avatar. The AI unexpectedly calls us...

Umar Khan: Baltimore Comedy, Real Life & National Takes 14.07.2025 1:29:58

Baltimore comedian Umar Khan joins us for a raw and hilarious breakdown of comedy, aging, marriage, and why he never chased the Hollywood dream. We talk about bombing on stage, green room gossip with Tim Dillon and Mark Normand, being too old to party, and the strange joy of staying local. From weed paranoia and Facebook fights to fighting waves of 10-year-olds and whether comedy is even worth it...

607 Unc: Dark Truths, Dirty Money & Divine Chaos | If This Doesn't Work... Ep. 79 07.07.2025 1:40:42

In this episode of If This Doesn’t Work… , we sit down with the one and only 607 Unc - and nothing is off limits. From letting his son sign a $2.3 million contract, to surviving prison, decoding the simulation, questioning history, and diving into vibrational energy, Unc delivers a raw and ruthless take on life, power, addiction, and what it means to really wake up. This episode blends dark humor,...

🍵👀 Liver King Lost His Mind… and So Did My Tinder Match 😺🐠 | Ep 78 30.06.2025 1:34:26

Liver King is out here challenging Joe Rogan to a fight while I’m out here getting catfished by someone who said they “love hiking and long walks on the beach.”This episode of If This Doesn’t Work... is full of emotional damage, meat-based rage, and online dating regret.👉 We break down Liver King’s latest spiral (including the coffee enema??)👉 Share some tragic dating tales👉 And try to figure o...

Author Aly Anders Talks AI, Dark Humor & Her Books Including ‘The Writing in the Walls’ | Ep 77 23.06.2025 1:09:51

Published author Aly Anders joins us to talk about writing in the age of AI, getting published, and her newest book The Writing in the Walls. We dive into her journey as a Maryland-based writer, how AI tools are reshaping creativity, and sprinkle in our usual dose of dark humor.📚 Aly has three books out now and shares how she found her voice, her writing journey, and what aspiring authors need to...

Treasure Hunting Fever Feat. Rich Wilson Ep 76 16.06.2025 1:00:03

Host: Justin AndersonGuest: Rich WilsonProducer: Mike Caropreso⁠⁠Apple Podcasts- https://podcasts.apple.com/us/podcast/if-this-doesnt-work/id1366535800TikTok- https://www.tiktok.com/@ifthisdoesntworkpodcastInstagram- https://www.instagram.com/ifthisdoesntworkpodcast?igsh=NWxxeXNhbXpqYjFw&utm_source=qr

Vasectomies, Sexual Stuff and Mike Losing His Mind Feat. Eddie Jefferson Ep 75 09.06.2025 1:08:56

Host: Justin AndersonGuest: Eddie JeffersonProducer: Mike Caropreso⁠⁠Apple Podcasts- https://podcasts.apple.com/us/podcast/if-this-doesnt-work/id1366535800TikTok- https://www.tiktok.com/@ifthisdoesntworkpodcastInstagram- https://www.instagram.com/ifthisdoesntworkpodcast?igsh=NWxxeXNhbXpqYjFw&utm_source=qr

We Play a Card Game Called Going Deep and Get Too Honest and Feat. Mike Caropreso Ep 74 02.06.2025 59:43

Host: Justin Anderson Guest: Mike Caropreso Producer: Mike Caropreso⁠⁠ Apple Podcasts- https://podcasts.apple.com/us/podcast/if-this-doesnt-work/id1366535800 TikTok- https://www.tiktok.com/@ifthisdoesntworkpodcast Instagram- https://www.instagram.com/ifthisdoesntworkpodcast?igsh=NWxxeXNhbXpqYjFw&utm_source=qr

Discipline, Racist GoFundMe, and Stand Up Comedy Feat. Mike Adcock Ep 73 26.05.2025 1:38:25

Host: Justin AndersonGuest: Mike AdcockProducer: Mike Caropreso⁠⁠Apple Podcasts- https://podcasts.apple.com/us/podcast/if-this-doesnt-work/id1366535800TikTok- https://www.tiktok.com/@ifthisdoesntworkpodcastInstagram- https://www.instagram.com/ifthisdoesntworkpodcast?igsh=NWxxeXNhbXpqYjFw&utm_source=qr

Kanye's New Song, 50 Cent, and Drones Feat. Josh Grimes Ep 72 19.05.2025 1:05:00

Host: Justin AndersonGuest: Josh GrimesProducer: Mike Caropreso⁠⁠Apple Podcasts- https://podcasts.apple.com/us/podcast/if-this-doesnt-work/id1366535800TikTok- https://www.tiktok.com/@ifthisdoesntworkpodcastInstagram- https://www.instagram.com/ifthisdoesntworkpodcast?igsh=NWxxeXNhbXpqYjFw&utm_source=qr

Platonic Cuddling, Bits! Bits! Bits!, and Stand-Up Comedy Feat. Mo Noor Ep 71 12.05.2025 1:09:25

Host: Justin AndersonGuest: Mo NoorProducer: Mike Caropreso⁠Apple Podcasts- https://podcasts.apple.com/us/podcast/if-this-doesnt-work/id1366535800TikTok- https://www.tiktok.com/@ifthisdoesntworkpodcastInstagram- https://www.instagram.com/ifthisdoesntworkpodcast?igsh=NWxxeXNhbXpqYjFw&utm_source=qr

Is Morality Made Up?, Dating in 2025, See Mikes Afro From High School Feat. Mike Caropreso Ep 70 05.05.2025 1:02:51