In this flashback episode, Rachel Bilson [The O.C., Jumper, Hart of Dixie] joins Anna to talk about heartbreak, motherhood, trusting your intuition, the O.C., the O.C. podcast and more. Anna also pulls out a few cards from her Dealbreakers game, and asks Rachel what she would or would not accept from a hypothetical romantic partner. Later in the episode, Anna and April Beyer talk with a listener who has trouble separating her job persona from her romantic persona and feels like she’s too much of a boss for men to handle.

To hear more from Rachel, check out her podcast Broad Ideas with Rachel Bilson!