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 to the agency president.
One of Hank's beautiful exes turns up with a big surprise that rocks his world, but ultimately his heart remains with Karen; Charlie and Marcy have financial woes, until Stu steps in with an offer that might be too good to refuse.
Hank collaborates on a musical with a rock star while taking up with his beautiful muse; Charlie and Stu compete for Marcy; Marcy falls under the spell of a radical feminist; Becca drops out of college to become a writer.
Hank writes the screenplay for a violent rap star and gets into hot water with his beautiful but dangerous girlfriend; Charlie dates his son's nanny; Karen's marriage deteriorates due to Bates' drinking.
Hank's literary sex scandal has caused a sensation, even as he prepares to defend himself in court and tries to get Karen and Becca to speak to him, and a movie based on his stolen book begins production.
Hank becomes a college writing professor and immediately gets romantically involved with a student, a fellow teacher and the dean's wife; Karen takes a job back in New York, leaving Becca with Hank; Charlie is seduced by his new boss.
Hank ghost writes the memoirs of a rock and roll legend while trying to reconcile with Karen; Becca's heart is broken by her first love; Charlie tries to enter the porn industry; Marcy goes to rehab for an addiction.
Hank is shocked that Karen is engaged and ponders his career trajectory from respected novelist to screenwriter to blogger; Charlie's fling with an assistant has dire marital consequences; a sexy teen steals something from Hank.