Maggie and Denise plan a summer vacation in Greece. Denise realizes that her parents may not allow her to go, let alone agree to finance the trip, because of her terrible grades. She plans to soften up her mother during a weekend visit. Clair arrives at Hillman on her own after Denise fails to pick her up on time, and Lettie unwittingly fills her in on the trip. Clair refuses to let Denise go to Greece. She and Cliff have decided to make Denise get a summer job, in the hopes that she might take her education seriously if she helps finance it. Denise believes that her parents consider her worthless, but Clair eases her mind. Jaleesa decides to join Maggie in Greece. Whitley fears that she will have to spend her birthday alone after Millie bails on her because of plans with Ron. She does not realize that Millie and Ron have thrown together a surprise party.

Clair Huxtable attends the Hillman job fair to conduct a seminar on business etiquette. She brings teenage daughter Vanessa and a friend in the hopes of convincing Vanessa to attend Hillman. (She and Dr. Huxtable would like to have a child actually graduate from their alma mater.) Dwayne has a disastrous interview with the Kinishewa electronics company. Clair agrees to lobby the company rep--a longtime friend who is attracted to her--on Dwayne's behalf. Vanessa and Kara ditch Whitley and Jaleesa so that they can cruise the campus alone. The girls lie about their age and identity and convince Dwayne and Ron to take them out. The foursome runs into Clair and Phillip at a restaurant. A fuming Clair drags the girls away, and Dwayne gets his internship.

Dwayne drives Whitley to New York for her father's wedding. He drops in on the Huxtables, hoping to rekindle his relationship with Denise and convince her to return to Hillman. Denise sends him reeling with the news that she married a Naval lieutenant during a sojourn to Africa, and is the stepmother of a three-year-old girl. Whitley becomes depressed about her father's marriage. She believes that he will forget her as he starts a family with his new wife. Dwayne and Whitley compare notes about their personal crises. They get caught in a blizzard, and Whitley's car suffers a flat tire. She and Dwayne huddle in the back seat and continue to comfort each other. They begin kissing, but are jarred back to reality by the tow truck's arrival.

Clair Huxtable visits the Hillman campus to videotape the students discussing their goals for the future. Although the taping is supposed to resemble a professional interview, Clair winds up playing the role of counselor. Freddie opts out of the interview in order to work on an archaeology assignment. She notices discrepancies between the Gilbert Hall laundry room and its original blueprints. She knocks down a wall and discovers a hidden room, which was part of the Underground Railroad that aided escaping slaves. Freddie is overwhelmed by her discovery and vows to make a difference with her life.