Theo wants to impress a girl by wearing an expensive shirt by designer Gordon Gartrelle. Since Cliff and Clair will not pay for it, Denise offers to make a copy of the shirt for him. Guest appearance by Kadeem Hardison, who years later would portray Dwayne Wayne on the Cosby Show spinoff, A Different World.

Cliff and Clair receive a visit from an old friend—and he has a new girlfriend that is half his age. They are initially suspicious, but learn that judging by appearances isn't always right.

Rudy invites all of her friends over for a slumber party. It's Cliff's job to watch over them, and he demonstrates some unique games to wrangle the youngsters. In the end, Russell drops by and demonstrates the perfect way to deal with kids-bribe them!

When Rudy's pet fish, Lamont, dies, Cliff tries to bring the family together for a funeral in the bathroom. The festivities end when Rudy gets bored and leaves to watch TV.

Vanessa claims that she is old enough to watch a scary movie, but Cliff still forbids it. Vanessa sneaks out anyway, but ends up having nightmares as a result.

Denise has a new boyfriend, David, but is reluctant to bring him home. She fears that Cliff will, like always, make fun of the boy and ruin her chances with him. Cliff and Clair are initially impressed with David until he expresses some unwanted opinions about medicine and the law at dinner. Kristoff St. John plays boyfriend David.

After Theo claims that he'll have no problem making it in the "real world", the Huxtables convert their house in the "Real World Apartments" and teach him a lesson about the real world; i.e., needing employment and references to get an apartment, income to get a bank loan, having to pay for his meals, etc. Carl Anthony Payne II as Cockroach.

For Russell and Anna's 49th wedding anniversary, the family commissions a portrait of the couple as newlyweds, and offers them a cruise to Europe. Later in the evening, the whole family performs Ray Charles' "Night Time Is the Right Time", with Theo, Rudy and Cliff each lip-synching a solo. Earle Hyman as Russell. Clarice Taylor as Anna.

Vanessa and her friends sneak out of town to attend a concert in Baltimore, but encounter huge problems along the way. Afterwards, she must face the wrath of Cliff and an infuriated Clair.

Clair is furious when Theo brings home a report card with 4 D's. He tells Cliff that he has no intention of going to college, as he feels that he is destined to be a ""regular person."" Cliff uses Monopoly money to teach him about the economic realities that many blue-collar workers must face. He assures Theo that he only wants him to try his best. Cliff is alarmed to meet Denise's latest beau, a former merchant marine who once spent time in a Turkish prison.

Cliff's father, Russell, pays a visit and begins questioning Cliff about the kids' college choices. He asks Denise about Hillman, his and Cliff's alma mater. Denise is dead-set against it at first, until Russell tells her that the males outnumber the females there. First appearance of Earle Hyman as Russell Huxtable, Cliff's father.

While Clair cares for a friend's baby, she begins to consider having another. Cliff desperately tries to talk her out of it, claiming that babies are "false advertising." Clair's mother, Carrie, then reminds her that the older you are when you have kids, the older you'll be if they end up having to come back and live at home. First appearance of Ethel Ayler as Carrie Hanks, Clair's mother.

Vanessa plays clarinet in the school's orchestra. Though she tries her best and practices daily, she simply cannot play the instrument. She plays an embarrassing solo at the school concert, but her parents support her anyway. Guest Dizzy Gillespie as Mr. Hampton, Vanessa's music teacher.

Clair is exhausted from constantly caring for the children. Cliff decides to take her out on the town for "You're Not a Mother Night." They go to a fancy restaurant and hotel. While there, some of Clair's motherly instincts start kicking in-but they stop in time for a romantic evening.

Cliff complains about the poor quality of his annual Father's Day gifts. He challenges the children to find some better presents for a December Father's Day. They give him thoughtful-if not quite attractive-presents.

Cliff's college track coach contacts him and asks to run in a charity event between Hillman and its rival, Norton College. Heathcliff "Combustible Huxtable" trains, but soon learns that he is not the runner he was all those years ago.

Denise invites Martin's ex-wife Paula for Thanksgiving dinner. Clair continues to send Cliff to the store for last-minute groceries, despite the fact that it is a cold and rainy Thanksgiving Day. Victoria Rowell as Paula.

Cliff, who has a fetish for electronic appliances, buys a juicer. Rudy and Peter, bored from Vanessa's inattentive baby-sitting, decide to use it even they are not allowed to use appliances. David Langston Smyrl as Mr. Lucas. Peter Costa as Peter.

Cliff plays pinochle with his father, a former teacher, and a friend. Theo buys a cheap ring for his girlfriend Tanya. Earle Hyman as Russell. Roscoe Lee Browne as Dr. Foster.

Cliff, Elvin and Martin secretly compete to determine who is the most romantic husband in the Huxtable family.

Sondra breaks up with her boyfriend Elvin and is depressed, taking it out on the family. Cliff and Clair aren't exactly unhappy; they find Elvin rather annoying. Later, he appears at the house with flowers and tries to apologize. While there, he offers some of his sexist rhetoric to Clair, who quickly becomes annoyed. First appearance of Geoffrey Owens as Elvin. Joseph C. Phillips appears as Daryl (Phillips joins the cast in Season 6 as Denise's new husband, Navy Lt. Martin Kendall)

Denise asks Cliff to talk to her friend, who has a medical problem. Cliff diagnoses the girl as having a mild bladder infection, but learns that she was wary of telling her parents without certainty. Cliff and Clair decide to show the kids that they can tell them anything, but the children quickly point out that their parents will just get angry. Cliff admits that anger is part of problems, but tells the children that no matter what, they will be loved.

Peter goes to the dentist, but has Rudy come along for moral support so Peter won't be afraid of the dentist anymore. Danny Kaye (in one of his last appearances) as Dr. Burns, who is also Cliff's dentist.

After his limo collides with Denise's car, Stevie Wonder (appearing as himself) invites the Huxtables to a recording session. Wonder performs "I Just Called to Say I Love You" with Clair and the family. Absent: Sabrina Le Beauf as Sondra Huxtable.

When friend Suzanne accompanies Denise to observe the Huxtables' normal behavior, a smitten Theo behaves far from normally. Robin Givens as Suzanne. Blair Underwood as Mark.