Swift Kick with a Frozen Boot

We get into some good old-fashioned drama with questions about dating a friend's crush and working for someone you hooked up with. See omnystudio.com/listener for privacy information. 

A FULL FOLLOW-UP episode! We check in on question askers past and see where Iliza's advice has left them, and where they might have buried the lead. Episodes where the questions originally aired: Fred is cheating on Wilma: Don't Google BTK (2/18/2026) Skiing with a Tinder match: ...  Show more

Conan chats with Trisha in Minnesota about working as an investigative crime reporter on real-life cold cases.

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Conan talks to Sam in Chicago about designing cryptid-themed adult toys and accessories.

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Actor and comedian Kevin Nealon feels absolutely duped about being Conan O’Brien’s friend.

Kevin sits down with Conan once more to discuss producing the documentary Come See Me in the Good Light, planning their road trip together, taking risks in life, and ...