Jimmy spends a day with a woman from his past and attempts to fit in with her friends while Gretchen attempts to impress Boone's ex-wife. Lindsay reconnects to a former father figure and Edgar, prompted by Max, buys a fancy car he can't afford.

Gretchen spends the day with Boone and his daughter in an attempt to distract herself from having slept with Jimmy the previous night, while Jimmy tries to prove to himself he's moved on. Lindsay attempts to save Olivia from getting too close to the unreliable Gretchen, and Edgar trails Max to figure out why they're no longer writing partners.