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. That night, Hank and Karen meet Charlie and Marcy for drinks. They wind up bumping into Sonja, the vomiting Scientologist from season one, who, 's now pregnant, and her new boyfriend Julian, a renowned self-help guru. The group heads to a party at the home of legendary record producer Lew Ashby, where Hank has an accident when he confuses a partygoer for Karen. On the ride home, 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. In prison, Hank is reintroduced to fellow inmate Lew Ashby, who proposes that Hank write Ashby, 's long-awaited biography. When Hank refuses, Ashby bails them both out and tells Hank a story of the girl he loved and lost. Meanwhile, Charlie gets fired after his former assistant, Dani, plays the agency president a montage of Charlie, 's self-pleasuring office sessions.

On Hank, 's first day as biographer to Lew Ashby, he, 's reintroduced to Trixie, the hooker with a heart of gold, who stirs up trouble by claiming that Hank is better in bed than Ashby.When Karen and Sonja meet to discuss a renovation project, Julian interrupts to work his guru magic on Karen. Becca grudgingly starts her first day at Mia, 's private school, where she meets an unexpected friend, Damien. Meanwhile, Charlie spots one of Marcy, 's clients, a porn actress named Daisy. While pitching himself as her agent, Charlie hops a ride with Daisy only to realize that he, 's in the middle of an impromptu porn shoot.

Hank and Karen throw a dinner party for a few close friends: Charlie and Marcy, Ashby, Sonja, Julian and Mia. Becca and her new boyfriend Damien round out the group.

In order to distract Hank from his heartbreak, Ashby arranges a sex session with popular, yet incredibly annoying, celebrity chef, Chloe Metz. Meanwhile, Charlie takes on a new client, Daisy, who, 's eager to land the lead in a porn film called Vaginatown, a remake of Roman Polanski, 's Chinatown. Charlie meets with the film, 's director, Ronny Praeger, 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. He discovers she, 's now a Beverly Hills wife and mother. Later, Hank accidentally walks in on Julian going at it with a rocker chick he, 's , mentoring, . When Hank confronts Sonja about the discovery, she reveals that, much to her frustration, they have an open relationship. Mia spends the day trailed by Rolling Stone reporter Annika Staley. After finagling their way into Ashby Manor, Hank takes a liking to Staley, but is shocked to discover Mia leaving Ashby, 's bedroom later that night. Meanwhile, when a location falls through, the Runkle residence is transformed into the set of Vaginatown. The lead actor, 's failings force Charlie to step in for the money shot.

Hank has found a new love interest, Becca's English teacher, who he discovers is the mother of his daughter's boyfriend. Charlie finds out that Marcy has been hiding a financial secret from him, one which may devastate them.

Hank attempts to get Ashby to confess. Charlie gives in to temptation.

hank refuses an offer. Karen and Ashby go on a date. Charlie and Daisy get to know each other better.

When Hank and Karen go see a doctor, they flash back to the past, when Karen first got pregnant. In the meantime, Charlie continues his special relationship with Daisy, while Marcy is still in rehab.

Ashby celebrates the publication of Mia’s book by hosting a party. Charlie asks Marcie for a divorce, now that he has completed rehab. And, Becca feels devastated by Damien’s cheating.

Hank finishes up Ashby's biography. Charlie takes a job at a car dealership since he has not been able to find one as an agent. Meanwhile, Sonja has her baby; and Hank and Becca face difficult decisions when Karen decides to move to New York.