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Latest Episodes:

391: Tongue in Cheek Kiss Jul 15, 2019

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In this episode we discuss sexy tattoos, angry boyfriends, and kissing bosses.

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390: Shout Out Lightning Round Jul 08, 2019

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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.

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389: Sexile Island Jul 01, 2019

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In this episode we discuss casual sex with a millionaire, coworker crushes, and fantasy basketball drama.

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388: Drake's Wallet Jun 24, 2019

Show notes

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.

387: Prison (w/Middleditch and Schwartz!) Jun 17, 2019

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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.

386: Circumcision (w/Nic Rad!) Jun 10, 2019

Show notes

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.

385: To Doink or Not to Doink Jun 03, 2019

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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.

384: The Roommate Switch May 27, 2019

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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.

383: Ticklish Vagina May 20, 2019

Show notes

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.

382: Game Night (w/Hey Riddle Riddle!) May 13, 2019

Show notes

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-not-sell-my-info.

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