Denise Huxtable begins her sophomore year at Hillman and moves into Gilbert Hall. She meets her roommate, Jaleesa Vinson, a 26-year-old divorcée who is the subject of much rumor and innuendo. Denise feels uneasy around Jaleesa and asks Stevie Rallen, the resident director, to find her a new room. Denise decides to try harder to get along with Jaleesa, but Jaleesa is offended that Denise has gone behind her back. They get into an argument, and Denise moves in with wealthy Whitley Gilbert (for whose family the dormitory is named). Whitley drives Denise insane with her idiosyncrasies and generally self-absorbed behavior. Denise apologizes to Jaleesa and asks for another chance, and Jaleesa agrees to stop being so defensive. Meanwhile, overeager freshman Dwayne Wayne hits on every woman in sight.

Whitley goes to a jewelry store to buy a birthday present for her father. Freddie tags along because she enjoys watching Whitley ""power shop."" The clerk ignores them and is reluctant to open the display case. She also suggests a cheap watch, as she doesn't think that Whitley can afford any of the high-end merchandise. Freddie believes that the clerk is a racist and decides to leave. Whitley argues that the clerk probably thought they were poor because of their manner of dress. (Whitley had not changed after her tennis game.) Whitley spends a fortune to prove herself, but her friends argue that this only gives the clerk a fat commission. Whitley returns everything and tells off the clerk, getting the woman in hot water with her manager. The ROTC holds a retreat to teach civilians about life in the Army. Walter makes a fool of himself and loses a bet to Col. Taylor. Dwayne ignores Ron's instructions during a flag capture game. He gets lost in the mountains and comes in contact with poiso

Whitley is distraught when everyone, including Julian, seems to have forgotten her 21st birthday. Kim has actually remembered, and is planning a girls-only surprise party. Dwayne and Ron decide to kidnap Whitley and throw her in a fountain for some reason. Kim fails to thwart their plans, but Ron falls while climbing the dorm wall and injures his leg. A depressed Whitley gets drunk on cheap wine and has a dinner date with her photograph of Denzel Washington. The girls arrive to take her out; they agree that she should have told Julian about her birthday instead of expecting him to find out on his own. Jaleesa pretends not to care when she sees Walter on a date with the medic who treated Ron. Whitley apologizes to Julian for testing him.

Julian shows up to surprise Whitley, who wants nothing to do with him. Dwayne and Ron dress like women to get past the drug dealers and onto the ferry. They arrive at the police station to discover that they accidentally brought Julian's bag instead of the one with the drugs and cash. Paul and Eric search the house, failing to recognize Dwayne and Ron (who are still disguised as ""Diana"" and ""Rhonda""). They promise to return that night. The gang fears that the police will not make it in time because a storm has cancelled all ferry service. Kim, Freddie, Ron and Mandy head out in search of help. Whitley decides to sleep with Julian, but he doesn't think the timing is right. Dwayne hears the dealers coming and bursts into Whitley and Julian's room. Whitley gets into an argument with Dwayne after telling him that she is a virgin. As she opens the door to get him to leave, she gestures with a candlestick holder and cracks Eric over the head. The trio struggles with the men until Walter and