Cliff, Clair, and the children plan an elaborate celebration for Cliff's parents 50th wedding anniversary. The Huxtable's perform a musical number for the parents and take them to a club for music and dancing.
At school, a classmate starts flirting with Theo. Theo is flattered and interested, but he already has a girlfriend. Rudy wants to have a tea party and since her sisters are busy, she asks Cliff to the tea party.
Vanessa starts wearing makeup without her parents' permission. Clair talks to Vanessa and reminds her she must wait until she's 15. Meanwhile, Theo is taking a fire-safety class at school and quizzes his parents on procedures.
Theo has to rewrite a school paper on the 1963 March on Washington. Cliff & Clair, and Cliff's parents, who were actually there during the march, tell Theo what really happened and how they experienced it. He gets to really feel the event.
After a member of the Tuskegee Airmen makes a speech at Theo's school, Theo and Cockroach want to take flying lessons. Cliff and Clair agree, but then the reality of lessons and commitment hits Theo and Cockroach. Rudy has a new friend, Kenny.
Clair has a pinched nerve and has to stay in bed. Cliff and the children try to make her day easier by doing chores around the house. At college, Denise gets a D in one of her classes and is afraid to tell her parents.
Sondra comes home from college and brings Elvin along with her. Theo is written up in the school paper about his wrestling skills. Elvin helps him learn a few new moves and shares with Theo that he is going to propose marriage to Sondra.
Rudy is spending the night with her grandparents. Denise is going with friends to The Village and invites Vanessa to go with her. Theo is waiting for news to go out with a girlfriend. When that falls through, Cliff creates Mens Night.
Cliff is turning 50 years old and the family plans a lot of surprises for him. He finds out all the things that are older than him, get a key chain that works for everyone except him, and has a party with some special friends.
Sondra and Elvin announce their engagement. Since Cliff always says he knows everything that goes on, Clair and the kids decide to play a joke on Cliff about the engagement. He finds out before the joke and turns the tables on the others.
Both Cliff and Clair are sick in bed with the flu, leaving Theo in charge; Theo orders Vanessa and Rudy around to clean up the house while he takes the credit for it even though he's planning to go out with a girl.
Cliff takes Rudy & her friends to a fancy restaurant. All dressed up in their best clothes, they go to the restaurant. Chaos ensues despite Cliff's effort to show them elegance. Clair's sister visits and announces she wants to have a baby.