When Cliff tells Theo of some of the hi jinx he did when he was younger. Theo decides to try it himself. But he ends up damaging his apartment, which leads to the landlord throwing him out. So Cliff tries to some things with the man so Theo can move out of the house where he has been staying.
Denise & her husband Lt. Martin Kendall are leaving for the Navy base to live in a house chosen there but Denise forgot to call for approval so they find out last minute that there's no house available for them and return to Cliff's house. Meanwhile Cliff explains to little Olivia how babies are born in this world.
Claire sends Cliff to the store to buy some stuff for Thanksgiving dinner on a very rainy day and he returns soaking wet. Unfortunately he keeps forgetting some products and Claire sends him again & again. Meanwhile Denise invites Martin's ex wife to Cliff's house because she's all alone. Finally Cliff arrives home again just in time for Thanksgiving dinner.
Claire and Denise are going to the Caribbean and Cliff stays all alone with Rudy & Olivia. Rudy comes to him with a problem between her & her friends but Cliff's advice makes things worse for Rudy. Meanwhile Theo takes Olivia to the cafeteria and uses her charm to collect other girls' phone numbers. Also Vanessa tries to get her father's permission to go to another girl's party with older boys.
Theo meets Cliff & Martin at the cafeteria sitting with two willing beautiful girls. Later at the Huxtable residence Martin tries to explain to Cliff the situation on how he & Denise met and got married. Afterwards the family organizes a surprise for Cliff that will make him very happy.
Vanessa & Rudy comes to Sondra's house to babysit because Sondra & Elvin had planned to go to dinner with Elvin's old girlfriend & her sister but at the last minute she cancels her plans and suggests her husband go alone. Elvin goes to dinner but when he comes back he finds his lady angry. The next day Elvin & Sondra visit the Huxtable's house where Cliff tries to explain to him how women think.
It's Olivia's birthday and all she wants is a brand new tricycle, which she has all her friends help her search the entire house for when Cliff, who's supposed to be babysitting her guests, falls asleep.
Theo is upset his girlfriend might go to graduate school in another town. He and Elvin go to a nightclub; they hear the King of the Blues Riley Jackson. Turns out Cliff and Clair know Riley. He visits the family, helps Theo with his blues.
Rudy wants a sweater with fish that light up that are on sale at the mall, but she doesn't have enough money to buy it and becomes so desperate, she steals $2.30 out of the money Clair left out for the dry cleaning.
When Cliff finds women's lingerie in Theo's laundry, he and Clair soon realize that their son has moved in with his girlfriend, Justine. Meanwhile, Denise announces her plans to become a special education teacher
Claire receives an important case by representing a client who wants to protect a community center with a childhood playground which is about to be torn down and in it's place they will build an office center. Meanwhile Cliff's neighbor take Cliff out to buy a sports car.
Cliff's great-aunt, Gramtee, comes to visit and everyone is excited - except Olivia. Olivia wants to go to the zoo instead of a planned church visit. Gramtee tells stories of Cliff as a child and of a relative who was a slave years ago.