After reuniting at the end of Season One, Hank and Karen decide to pack up and head to New York. As part of the reconciliation, Hank undergoes a grueling vasectomy at Karen's request. Hank has an accident when he confuses a partygoer for Karen. Hank gets arrested for driving under the influence and assaulting an officer.

Hank finds himself in jail after assaulting a mouthy police officer. Karen, still upset at Hank for his accident at the party, refuses to bail him out. Meanwhile, Charlie gets fired after his former assistant, Dani, plays the agency president a montage of Charlie’s self-pleasuring office sessions.

Charlie wants to help Daisy with her porn career, while Hanks starts writing Lew Ashby's biography. Becca has her first day at a private school, while Karen meets Sonja and Julian again.

Hank proposes to Karen right before a dinner party, to which Mia, Charlie, Marcy, Lew Ashby, Sonja and Julian are invited. Drugs and special circumstances turn the evening in an unexpected direction.

In order to distract Hank from his heartbreak, Ashby arranges a sex session with popular, yet incredibly annoying, celebrity chef, Chloe Metz. Charlie takes on a new client who’s eager to land the lead in a porn film called Vaginatown. Charlie meets with the film’s director and secures her the part, but only after investing $100,000 of his own savings.

Hank decides to seek out Lew Ashby’s long lost love, Janie Jones. Hank accidentally walks in on Julian going at it with a rocker chick he’s “mentoring”. Mia spends the day trailed by Rolling Stone reporter Annika Staley. The Runkle residence is transformed into the set of Vaginatown.

Hank attempts to find a love interest for Becca's teacher. Charlie uncovers Marcy's secret which could have fatal effects on their finances.

Hank tries to get the truth about Ashby; Karen confronts the record producer; Marcy detoxes at her mother's house; Charlie succumbs to temptation.