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.

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'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.

A new threesome including Hank and Charlie evolves from a meeting at the gym, while Karen and Marcy have a girl's night out at which they decide to surprise Hank and Charlie.

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.

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.

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.

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.