Segments

In this episode we discuss being newly single, high school crushes, and unrequited love. For more advice, check out our bonus Thursday video episodes on our Patreon . See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss Jake's mental health, high school, and dry spells. For more advice, check out our Patreon which has bonus video videos every Thursday! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss Jake's 34th birthday, Amir's music career, and breaking the law in very small ways. For more IF I WERE YOU check out our Patreon -- bonus video episodes every Thursday! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss racist mugs, smelly thugs, and gift baskets. For more IF I WERE YOU, check out our Patreon -- Bonus videos every Thursday! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Musician and friend Julia Nunes is in the studio discussing flirting, exercising, and laser eye surgery. Get Julia's new album UGHWOW wherever you listen to music. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss sexy tattoos, angry boyfriends, and kissing bosses. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this lightning round episode we discuss our favorite weather, our favorite foods, and what Dungeons and Dragons character would Amir be.... WITH A SIDE OF RICE. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss casual sex with a millionaire, coworker crushes, and fantasy basketball drama. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss pre-marital problems, MMF threesomes, and porn blogs. For more "If I Were You" check out our bonus Thursday video episodes on our Patreon ! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Friends and comedians Thomas Middleditch and Ben Schwartz join us live from Thalia Hall in Chicago to discuss foreskin, new pants, and who is 58 years old. Thanks to everybody who came out to HeadGum Live last weekend! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Friend and father Nic Rad is on the show to talk about difficult decisions, pop music, and of course, ladders. And if you see this in time, come hang out with us in Chicago! HeadGum Live is coming June 14-16 at Thalia Hall! Get your tickets here . See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss oral hygiene, loving thy neighbor, and the Toronto Raptors. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss ending relationships and ending Game of Thrones... and smiling at yourself. Come hang out with us in Chicago on June 14-16 at HeadGum Live ! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss laughing during sex, new tools, and a Twitter draft so good, it's worth a Golden Mic award. Still some tickets left to see us in Chicago! Click here to join the party . See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Fellow HeadGum podcasters Adal Rifai, Erin Keif and JPC ( Hey Riddle Riddle podcast) join us to discuss breaking the ice, solving riddles, and how to poop. For more riddles and puzzles, check out Hey Riddle Riddle on HeadGum. See us all at HeadGum Live in Chicago June 14-16 at Thalia Hall! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do...

In this episode we discuss hot bosses, motorcycle uncles, and phone numbers. Then Jake gives out this episodes Golden Mic and Turdy awards. Come see us in Chicago on June 15 ! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss overthinking pillow talk, underthinking bootie calls, and Jake's newest award. Come see us live in Chicago on June 15 as part of HeadGum Live! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss blurry vision, self-defense, and Jake's newest creation: General Cleanliness. Support the Golden Mic Winner (Jake) by purchasing his very own shirt. https://store.headgum.com/collections/apparel/products/general-cleanliness-tee See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss adopted siblings, Jake's childhood, and Amir's LASIK. HeadGum Live! Is coming to Chicago on June 14-16. Come hang with us and our friends -- tickets here . See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss prom-posals, cheating zaddy's, and Amir's new musical. Recorded at the Black Cat in Washington DC! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss Amir’s April Fools Day LASIK, coed wrestling, and of course, jade rollers. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Friend and fellow HeadGum podcaster Kevin Porter joins us as we discuss dogsitting, candles, and his podcast "Good Christian Fun!" See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

In this episode we discuss roller coaster pranks, tutor crushes, and art school threesomes -- Live at the Gramercy Theatre in NYC! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

New HeadGum podcasters Laura and Rachel stop by to discuss their show " Girls on Porn " and answer as many porn-related questions as we can get through in a good old fashioned porn lightning round episode. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

Comedian and fellow HeadGum podcaster Nicole Byer joins us to discuss dating, flying, and dressing yourself. And for more bonus episodes of If I Were You check out our Patreon page: www.patreon.com/JA See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .