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.

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.

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.

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.

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.

Bill and Lillian consider moving into the first integrated neighborhood in Montgomery; Dean develops a crush on Brad's mom during a sleepover at their house.

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.

Struggling to figure out where he fits in, Dean decides to pursue his calling as "The Great Uniter" and attempts to organize the first integrated baseball game between his team and his friend Brad's team.

While Dean reckons with his first taste of heartbreak and betrayal, the adults in his life are overly empathetic and assume his grief is from mourning current events.

Dean stumbles upon some “racy literature” and shares it with friends at school. When he is caught by the school principal, Bill and Lillian navigate uncharted territory as parents and Dean learns that manhood isn’t all it’s cracked up to be.

It’s “Take Your Son to Work Day” and Dean heads to band practice with Bill. But the “grown folks’ business” at the music studio prompts Lillian to have to pick up Dean. While at her office, Dean finally learns what his mom does while he’s at school all day, gaining a newfound respect for her career and ambition.

Dean is reluctant to attend the annual church lock-in until Kim tells him it’s where she got her first kiss. He enlists his friends to help him pair up with Keisa, but his plans are thwarted when he instead gets paired up with the pastor’s daughter, Charlene.

When Coach Long and Bill take the boys on a camping trip as part of their newly formed scout troop, their starkly different approaches to the outdoors show Dean that his father isn’t good at everything. As a thunderstorm threatens an eerie quest through the woods, Bill leans into his expertise to save the day.

As Kim’s campaign for a car coincides with the need to take Grandaddy Clisby’s keys away, Bill proposes a solution that is only pleasing to him: Kim can drive, so long as she takes her grandfather and Dean around town. Later on at the mall, Dean is worried about seeming uncool when Clisby ends up chaperoning him and his friends, but Clisby has a few crowd-pleasing tricks up his sleeve.

After seeing Dean bullied by Michael after school Lillian goes to confront his parents and learns he needs more compassion than discipline. Much to Dean’s dismay, she takes Michael under her wing and helps him with his project for the science fair – an event where Dean typically excels

Dean can’t wait to spend Christmas with his older brother, Bruce, when he returns home from Vietnam. But adjusting to life back in Montgomery comes with unexpected challenges for Bruce, and the rest of the Williams family rely on their favorite holiday traditions to bring cheer

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.

Brad works through his nerves preparing for his bar mitzvah speech while Dean ends his friendship with Keisa when Charlene tells him he can’t be friends with other girls. Things come to a head when the whole group comes together to celebrate Brad’s bar mitzvah.

When Dean loses his position as first chair saxophone in the school band, Bill lays the pressure on him to earn it back.

Dean’s plans to ask Keisa to the Valentine’s Day Dance are foiled when another boy asks her out first after a new makeover makes her the talk of the school. Meanwhile, Bill and Lillian make Kim sign up for a Big Sister program to have extracurricular activities for her college applications.

The family spends spring break with Lillian's parents in the countryside, and Dean lies to his cousins about city life in Montgomery to impress them. Meanwhile, Lillian helps to settle a land dispute between her parents and their neighbors to impress her difficult-to-please mother.

When their teacher goes on maternity leave, Dean, Cory and Keisa are excited to be taught by Mr. Brady, the school’s first Black teacher. Mr. Brady encourages the students to try out for the Knowledge Bowl team where Dean faces some unexpected challenges