It’s the summer of 1969, and Dean and Bill are experiencing new walks of life in New York City where Dean has tagged along for Bill’s career-making songwriting gig. Back in Montgomery, Lilian’s infamous sister, Jackie, pays a memorable visit.

Torn between his secret relationship with Keisa and his friendship with Broderick, Dean turns to Jackie for advice. Meanwhile, after her latest run-in with the law, Jackie decides to turn over a new leaf.

As Kim decides to take classes at Bill's college and date one of his star students, Bill must walk the line between teacher and dad; Dean and his friends join the football team where Dean finds himself in a tricky situation.

When Lillian joins the church choir, she discovers a new side to her mother-in-law; Kim encourages a guilt-ridden Dean to have an encounter with the supernatural.

After Bill befriends Dean's music teacher, Bill and Lillian attend a party at his house and the evening takes an unexpected turn. Meanwhile, with their parents away, Dean, Bruce and Kim make their own plans for the night.

In search of a new hobby, Dean joins the drama club - only to find himself mixed up in drama of his own. Bill and Kim grapple with Bruce's choice to campaign for a local politician.

After Lillian's boss announces budget cuts, she is forced to make a decision and enforce boundaries between her personal and professional life. Meanwhile, Dean and Cory's friendship hits a few speed bumps as they work together for the boxcar derby.

The Williams gather to celebrate Clisby's 75th birthday - including Bill's brother Melvin and his daughter Cassie. While Bill and Melvin try to one-up each other for Clisby's approval, Cassie shares big news with Lillian and Kim.

When the Williams family decides to go on a family vacation, Kim suggests a road trip to Austin College and Dean proposes a stop at Disneyland. After meeting up with his old bandmates, Bill reflects on his life choices.