A self-loathing, alcoholic writer attempts to repair his damaged relationships with his daughter and her mother while combating sex addiction, a budding drug problem, and the seeming inability to avoid making bad decisions.
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 turns down an offer of sex which is unthinkable (for him). Karen gives in to Ashby's asking and agrees to date him. Charlie and Daisy have a bonding moment over the film Dirty Dancing, while Marcy is still in rehab.
Hank completes his biography of Ashby. Charlie is reduced to working at a car dealership. Sonja gives birth. Karen accepts a job offer back home in New York, forcing Hank and Becca to make painful choices.
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