A transplanted author suffers from writer's block and is disappointed that his novel has been turned into a romantic comedy for the big screen. He also learns his ex is engaged and that their 12-year-old daughter is acting on her “emerging sexuality.”

Hank begins his blogging job at Hell-A-Magazine. Karen is able to set Hank up with her friend Sonja by disguising the get together as a family dinner. At dinner, Becca reveals how Hank met Karen.

At a book signing, Hank gets into a scrap with the disgruntled director of the film based on his novel, and later runs into a woman whom he embarrassed and insulted on a blind date. Mia attempts to steal some of Hank's work to use for her high-school creative-writing class.

Meredith convinces Hank to escort her to an environmental fundraiser. Coincidentally Bill and Karen are at the same event, where Karen makes a scene. Also, Hank runs into Dani and Charlie while they are in his office.

Bill asks Hank to step in as a guest speaker at Mia's creative writing class. During a radio interview, Hank talks about his writing and motivations. Meanwhile, Becca develops a crush on her guitar teacher Dave, but he ends up with Mia.

Hank spends the night with a sexy surfer girl and in return she robs him. Mia wants more of Hank's writing to pass her class, instead he offers her to help her with her own writing. Charlie wants to spice up the sex life with his wife, but she is not as fond of spanking as Dani is.

Hank is disturbed by Becca's negative reaction towards the concept of happy endings, even more so when he finds out that it is partially his fault.

Marcy comes up with the idea of a threesome with Charlie and Dani, but it ends unexpectedly.

Hank's father dies. Despite the memories of his father floating to the surface, he doesn't want to go to the funeral. To ease his pain, he goes to bed with a hooker named Trixie, despite the fact he doesn't have enough money to pay her. Meanwhile, Karen does her best to help him overcome the pain.

After the funeral of Hank's father Al, Hank comes back to L.A. with a new manuscript, that he wants Karen to read. After receiving a bonus paycheck, he buys a new car for himself and a new guitar for Becca.

As Karen's wedding to Bill nears, Hank struggles with accepting what appears to be inevitable. Bill informs Mia that he will not allow her book to be published and Hank has a unique solution to dealing with Becca's surprise visitor.

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.