After their reunion in season one, Hank and Karen plan to move back to New York. Karen asks Hank to get a vasectomy, to which he agrees. At the party of a record producer, Lew Ashby, Hank has a sexual accident...

Hank ends up in jail and makes a new friend there, while Charlie runs into job trouble after a fight with Dani.

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.

After being dumped by Karen, Hank dreams about sleeping with a popular cooking show host, Chloe Metz.

Charlie helps Daisy by getting her a role in the porn film "Vaginatown".

Hank wants to find out more about Ashby.

Hank attempts to find a love interest for Becca's teacher. Charlie uncovers Marcy's secret which could have fatal effects on their finances.

When Hank visits Janie Jones to find out more about Lew Ashby, but he finds out something even more interesting about her maid. Karen finds out about Mia dating Lew Ashby and confronts him about it. Charlie continues to manage Daisy, while Marcy is on the way to a detox.

Daisy fills in for Marcy at "Hot Lips" and while watching "Dirty Dancing" with Charlie. Hank goes out with Janie Jones to an art exhibition, where they run into Sonja and Julian. Lew Ashby invites Karen on a date.

Hank reminisces his past with Karen. Charlie pleads with Daisy to move out.

Ashby throws a party for Mia for her book being published. Charlie wants a divorce. Becca is distraught after catching Damien two-timing on her.

Hank finishes his biography. Karen is given a job offer she can't refuse resulting in Hank and Becca to make sacrifices.