Bill and Lillian decide to join high society club Lads & Ladies as a way to introduce Kim and Dean to positive influences in the community. Bill, Kim and Dean fit right in, but things take a turn when Lillian is treated differently for being a working mom.

When Dean comes down with the chicken pox on his way to a hunting trip with Bill and Grandaddy Clisby, Lillian forces the three of them to quarantine together. Clisby pushes homemade remedies on them out of his mistrust of doctors, but he’s forced to reckon with this when Dean’s condition worsens.

Dean tries to impress Keisa's cool new boyfriend by inviting him and his friends to a party Kim is throwing while Bill and Lillian are away for the night; things get out of hand just as Bill and Lillian arrive home.

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.

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.

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.