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.
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.
It's the end of the school year, and summer excitement is all around. When Bill and Lillian each receive major career opportunities, tension builds as they decide who will handle more of the household responsibilities. Meanwhile, Dean and Keisa take shelter together as a tornado tears through Montgomery, providing the perfect moment for Dean to tell her how he really feels.
Dean tries to impress Keisa's cool new boyfriend, Broderick, by inviting him and his friends over for 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, and Dean is forced to admit he isn't being true to himself.
Bill is excited to have made tenure at the university, only to find that his focus on career and family has cost him his spot in his band. Lillian encourages Bill to write and perform solo, especially as an attractive young jazz singer approaches Bill to collaborate. Meanwhile, Bruce adjusts to living at home.
Bruce returns home from Vietnam, and the family is shocked to find out he is dating an older woman with an 8-year-old son with whom he is eager to start his life. When they learn more about Bruce's latest deployment, they begin to understand his survivors' guilt and come together to support him.
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.
Kim is excited to start her new job as a waitress at the local diner.
When Dean learns that Corey's dad, Coach Long, is in the doghouse, he struggles to keep this secret from his friend.
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.
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.
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.
When Dean loses his position as first chair saxophone in the school band, Bill lays the pressure on him to earn it back. But after a talk with Lillian, Bill realizes he's being a bit too harsh and forcing his own dreams upon Dean.
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.
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.
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.
After seeing Dean bullied by Michael, Lillian confronts his parents; Lillian helps Michael with his science project.
Bill comes up with a solution for Kim's car desires, but the solution is only pleasing to him; Dean is worried about seeming uncool when Clisby ends up chaperoning him and his friends.
Coach Long and Bill take the boys on a camping trip as part of their scout troop. Their different approaches to the outdoors show Dean that his father is not good at everything.
Dean is reluctant to attend the annual church lock-in until Kim tells him it's where she got her first kiss; then he enlists his friends to help him pair up with Keisa.
Dean heads to band practice with Bill, but the grown folks' business at the music studio prompts Lillian to pick Dean up; Dean learns what his mom does while he's at school all day.
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.
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 milks the special treatment and uses it to his advantage – and his family shows their support for him in their own unique ways; Kim invites him to join her at a local activist rally, while Bill and Dean bond during a fishing trip.
As the youngest in the Williams family, Dean is struggling to figure out where he fits in. Between his brother's athleticism, sister's popularity, mother's intelligence and dad's overall coolness, everyone else seems to have their lane figured out. He 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.
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