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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 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.

As Karen is fitted for her wedding dress, Becca drops the news that she wants to live with Hank. Dani informs Charlie that she wants Mia’s book fast-tracked or else. Hank discovers through Charlie that it’s his work Mia’s been peddling. Furious, he tries to stop her, but she threatens to reveal their one night stand. Charlie finds out from Hank about Mia. Becca moves in with Hank and Karen stops by later that night, feeling that maybe this is where she belongs.
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Newly minted roommates Hank and Charlie meet a girl at the gym who knows Hank from a past incident and when Hank can’t quite remember her, she beats him up in the ring. Each reeling from relationship woes, Karen and Marcy decide to have a girl’s night out. Back at UTK, Dani meets with Mia regarding a novel she has written. Karen and Marcy decide to pay Hank and Charlie a surprise visit, but get more than they bargained for when they walk in on them and the girl from the boxing gym.
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Hank returns from his father’s funeral having written a new manuscript that he wants Karen to read. Charlie presents Hank with a production bonus check. Bill and Karen have last minute wedding jitters. Charlie tries to patch things up with Marcy after their threesome debacle with Dani.
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Hank falls into a spiral of despair when his father, Al, dies. Holing up with a hooker named Trixie to numb his pain Hank recalls his estranged relationship with his father. In a series of flashbacks, we see Al’s last visit with Hank.
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Hank attempts to disprove Becca’s theory about the non-existence of happy endings by landing Karen a job and setting up an intimate dinner for the three of them. Charlie and Marcy decide to give a threesome a try with Charlie’s assistant, Dani. Mia finds herself in a compromising situation with her teacher.
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Hank meets sexy Surfer Girl at the market. After a night getting high while listening to vintage rock LPs and having sex with her, Hank awakens to Mia, who needs more of Hank’s writing to pass off in her class.
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Bill arrives at Hank’s asking for a favor - will Hank speak at Mia’s creative writing class? Hank relents, but not without taking something in exchange. Hank wins over the sexy students at Mia’s all-girl school and also learns some surprising things about her teacher. Plus, Becca’s pre-teen crush on her guitar teacher ends in her first heartbreak.

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In a bid to spark more than a vertical relationship with Hank, Meredith convinces him to escort her to an environmental fundraiser. Before the event, Hank stops off at Karen’s to deliver a gift for Becca and learns Karen is off coincidentally to the same function.
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