This season, Hank and Karen will finally rekindle their long-lost romance. But their road to love will hit a major snag when Hank's new job as biography writer for a legendary music producer lands him waist-deep in his three favorite vices — sex, drugs, and rock & roll. Meanwhile, daughter Becca is growing up way too fast; best friend and agent Charlie and wife Marcy are working through the fallout from last season's affair; and Hank's newest book is a huge hit — for someone else, who stole the manuscript from him and is basking in her newfound, totally unearned fame. But nothing gets good old Hank down for long — it's all just another day in the city for our favorite hedonistic scribe.

This season 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, and Becca drops out of college to become a writer.

In the present, artist Tom Warshaw recalls his traumatic coming of age. As a 13-year-old growing up in New York City in 1973, Tom hangs out with Pappass, a mentally disabled man. With Tom's mother battling depression after the death of her husband, the young boy is left to his own devices. When Tom develops a crush on schoolmate Melissa, Pappass feels abandoned and begins behaving erratically.