Awkwardness reaches new heights when Evan invites his ex-girlfriend Chrissy Sampson onto the podcast, as they speak for the first time since she dumped him in 2003. Evan and Chrissy reminisce about Long Island nightlife, especially Levittown’s Munchaba Lounge (3:32). Chrissy then chronicles what it’s like to live year-round in the Hamptons (in her 30s) and unveils some details about a book she is looking to publish (15:00), which means she needs to have a snobby author bio (17:25). And before talking about her career as journalist (21:23), Evan asks Chrissy about how she has unintentionally had a knack for dating Jewish guys (18:36). Grab some popcorn, because things definitely get awkward.

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