Hank and Karen plan to move back to New York together, but their reunion is short-lived thanks to a series of drunken incidents and Hank's subsequent arrest.
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Hank befriends a legendary record producer in jail and considers writing the man's biography. Charlie loses his job when his scheming former assistant Dani betrays him.
Hank's first day as Lew Ashby's biographer is complicated when a hooker acquainted with both men claims that Hank is better in bed. Karen comes under the spell of a self-help guru while Charlie pitches himself as agent to a porn actress.
Hank and Karen's dinner party is derailed by Hank's botched marriage proposal to Karen, the revelation that Hank is likely the father of their friend Sonja's baby, and Lew's near-death from an allergic reaction to sushi.
The newly-single-again Hank moves into Lew's mansion, where his host arranges a sexual encounter for him with an annoying celebrity chef. Charlie becomes a major investor in a porn movie.
Hank sets out to track down Lew's long-lost first love, and discovers that Sonja and her self-help guru boyfriend Julian have an open relationship. Mia spends a day trailed by a Rolling Stone reporter while Charlie's house becomes a porn set.
Hank meets an attractive new love interest in Becca's English teacher, but it turns out she's also the mother of Becca's boyfriend. Charlie discovers that Marcy has been hiding a financially devastating secret.
Hank tries to get the truth about Ashby from his former flame, while Karen confronts the record producer about his relationship with Mia.
Hank declines an offer of sex, while Karen goes on a date with Ashby. Charlie and Daisy bond over Dirty Dancing while Marcy remains on the mend in rehab.
Hank nervously awaits medical test results while reflecting on the early days of his romance with Karen, which coincided with a famous grunge rocker's overdose.
Ashby hosts a party to celebrate the publication of Mia's book. Charlie announces to Marcy, who has just completed rehab, that he wants a divorce. Becca is devastated to catch Damien cheating on her.
Hank completes his biography of Ashby while Charlie is reduced to working at a car dealership. Karen accepts a job offer back home in New York.