In this flashback episode, Matt Walsh [Veep, Ted, Into the Storm] talks with Anna about getting his start in Chicago, revisiting VEEP on his podcast, Second in Command, what it really means to be a struggling actor, helpful and unhelpful career advice, early relationships, heartbreak, meeting his wife and more.

Matt and Anna then talk with Julie, who has had several friends and romantic partners accuse her of ghosting them and questions whether she did anything wrong. Next, they talk with Isabelle, who is engaged to a man whose political views conflict with her own to the extent that she fears for their relationship.