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's in for a hedonistic night to remember when Jackie and two stripper friends arrive at his doorstep, unannounced. The next morning, before Hank can escort his new friends from the apartment, Charlie shows up with a verbally abusive Rick Springfield. Hank’s forced to hide the hung-over party girls all over the house after Jill and Felicia pay surprise visits. The charade reaches its boiling point when Dean Koons arrives on the scene, resulting in a messy catharsis by fire.