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.

Jaleesa and Denise get a new roommate, talkative transfer student Maggie Lauten. Denise learns that the check for her dorm fees has bounced. To make matters worse, she had also covered Jaleesa's fees to repay her for an earlier favor. Denise and Jaleesa face eviction unless they can come up with 200 dollars by the next day. Denise cannot bring herself to ask her parents for help, as she is tired of being bailed out. When the dean of students realizes that Denise sincerely wants to take responsibilty for her actions, he helps her get a cafeteria job with an advance on her salary. Jaleesa takes delight in the fact that she is now Denise's boss.

Denise and Maggie convince Jaleesa to run for dorm monitor to prevent Whitley from getting the position. As one of her campaign promises, Jaleesa vows to address the dorm's litter problem by forcing anyone who fails to pick up after herself to wear a pig nose for a day. Denise leaves pizza in the lounge overnight, and Jaleesa orders her to wear the nose. Denise is furious, as she has a date with a cute guy from her biology class that night. They have never talked in person (she asked him out over the phone), so she decides to postpone the date because she does not want to meet him under these circumstances. Dwayne fails to get a hold of the guy as promised, but Michael still wants to go out with Denise. He even dons a pig nose so that she will not feel self-conscious.

Dwayne offers to tutor Denise in calculus after she receives a D on a test. Denise believes that it is a scam, but Dwayne turns out to be an excellent tutor. They study for so long that Dwayne gets locked inside the dorm after curfew. He sneaks into Whitley's room while she is sleeping and climbs out the window. Stevie catches Dwayne coming down the fire escape, and Whitley suffers tremendous damage to her reputation. Dwayne refuses to tell the truth because he fears that Denise could be suspended. Stevie believes that Dwayne and Whitley are lying, and plans to report them to the dean. Denise interrupts and explains what really happened.

Maggie prepares to debate Whitley on the topic of whether women can balance a career and family life. She is distracted by a surprise visit from her boyfriend, Mike, who stuns her by revealing that he has left school to take a job with the National Pork Council. He asks Maggie to transfer to a school in Washington, D.C. to be near him, and proposes marriage. Maggie is so overwhelmed by her relationship crisis that Denise must take her place in the middle of the debate. She wins easily by detailing the way in which her parents have employed compromise to make their situation work. Maggie and Mike take her words to heart and decide to slow down their relationship. Meanwhile, Dwayne tries to get a permanent spot on campus radio after successfully filling in for an ailing disc jockey.

Denise's little sister Rudy comes to visit for the weekend. She surprises Denise by immediately hitting it off with Whitley. When Denise and Rudy find it impossible to sleep in the same bed, Whitley allows Rudy to stay in her room. Whitley teaches Rudy all of her beauty secrets, and the two become good friends. Rudy hurts Denise's feelings by spending all of her time with Whitley. Meanwhile, Jaleesa fears the worst after hearing that her sister went to dinner with Jaleesa's ex-husband. Jaleesa clears up the situation, then asks Whitley to stop monopolizing Rudy's time. Whitley tells Rudy a bedtime story about two sisters and a snow queen. Rudy understands the moral of the story and agrees to pay more attention to Denise.

Denise is apprehensive about a visit from her grandfather, as she fears that she cannot live up to his expectations. Jaleesa and Maggie ask Denise to take part in a traditional homecoming prank by stealing the head of the rival mascot's bear costume. (They would be the first women in Hillman history to accomplish this.) Denise initially turns them down because she does not want to disappoint her grandfather. She does not realize that Russell tried to steal the bear head in 1935, but was bested by a friend. He is still bitter about this, and bets his friend that he can pull off the feat. Denise decides to help her roommates after Whitley angers her by belittling the prank as "foolishness." Russell and the girls separately seek the assistance of Hillman mascot Dwayne, who distracts the guys assigned to guard the mascot. Denise and her grandfather simultaneously try to steal the mascot head; they realize they have misjudged each other. The girls leave the head in Whitley's bed as revenge

Denise shows potential as a sprinter during P.E. class, and the track coach asks her to come out for the team. Her father is thrilled to have another Huxtable competing for Hillman, as he and his father both ran for the school. Denise enjoys the attention she receives from her friends and other students, but cannot handle the grueling practices. She considers quitting until a star runner informs her that she is not the only one who hates practice; in fact, the entire team feels this way. Maggie desperately tries to track down an economics book that she needs for a term paper.

Many of the girls become smitten with Byron Walcott, their handsome new geology professor. Professor Walcott's knowledge and enthusiasm for geology inspire Denise to develop a fascination for the subject. Although Denise mocks the other girls for their crushes on the professor, she also mistakes his attention for romantic interest. Stevie confronts Professor Walcott and accuses him of leading his students on. Dwayne witnesses their argument and suspects that they like each other. Denise feels like a fool for misreading Professor Walcott's intentions, but quickly gets over it. She plays matchmaker for Stevie and the professor. Maggie concludes that Americans require too much personal space; she gets on everyone's nerves by cutting down on her "body buffer zone."

Millie tells the other dorm residents that Whitley's parents are divorcing. Whitley tries to maintain a positive attitude, and looks forward to spending the holidays with her father in Switzerland. Mr. Gilbert stuns Whitley by introducing his new, much younger girlfriend; and springs the news that she will be coming along on their trip. Denise helps the devastated Whitley cope with the situation and try to come to an understanding with Monica. Jaleesa and Maggie continually rag on the gifts from their "secret Santas," unaware that they have come from each other. Dwayne arranges to become Denise's secret Santa, even though he is not from her dorm. Dwayne's friend Ron helps with his plan to woo Denise by acting as her man servant for the week.

Dwayne annoys a graduate student with his stupid pick-up lines. She predicts that Dwayne would freak out if a woman actually responded to his advances, and decides to invite him to her apartment. Jaleesa takes bets from the entire dorm on Dwayne's possible reaction. Denise feels that Dwayne does not deserve this treatment, and warns him that he is being set up. Ron persuades Dwayne to go to Peggy's apartment and win her over with his charm. Denise and Walter (Dwayne's resident director and P.E. teacher) try to convince Dwayne to be himself around women. Peggy realizes that Dwayne is a good guy and cannot follow through with the bet.

Denise volunteers for peer counseling duty during finals week. She proves to be a very good counselor, but uses the job as an excuse to put off a major history paper. Dwayne dislikes the head counselor, a laid-back surfer from California, because he suspects that he will put the moves on Denise. Whitley panics about an upcoming botany final; she had assumed that Millie's notes would be enough to carry her through the test. Dwayne and Ron express their discontent when the girls neglect their appearance while cramming for exams. The girls respond by holding an impromptu pageant in the dorm lounge to select "Miss Ugly America."

Jaleesa fills in as resident director after Stevie leaves the university to get married (to Professor Walcott?). The students attend a lecture by Lettie Bostic, a renowned world traveler. Lettie dropped out of Hillman and moved to Paris, where she kept company with Picasso and other artistic icons and even worked as a spy during World War II. She confesses that she still regrets quitting school, so the dean offers to give her credit for "life experience" if she takes over as Gilbert's resident director. During a dorm meeting, Lettie immediately rubs the girls the wrong way with her blunt comments. Jaleesa, who is bitter about losing her leadership position, organizes a revolt in the hopes of driving Lettie away. Lettie covers for the girls when they break a television set, and both sides agree to be less abrasive.

Denise befriends Cougar, an extremely intelligent and creative student from her philosophy class. Cougar asks Denise to sneak her into the dorm for the night, claiming that her roommate has been letting an annoying boyfriend sleep over. Although she is supposed to stay on the couch, Cougar tries to use Whitley's room while Whitley is in the infirmary receiving treatment for a sprained ankle. Cougar gets caught, and Denise lashes out at her. Cougar reveals that she is not really a student at Hillman. She is an orphan who has been homeless since age 15, and started showing up for classes to increase her education. Dwayne and Denise ask Lettie to lobby the dean to enroll Cougar on scholarship, but Cougar initially balks at taking the SAT.

Dwayne tries to use his radio show to get a Valentine's Day date. He invents a dream man named Darrell Walker in the hopes of eliciting attention from the ladies. Although everyone else realizes that Darrell is obviously Dwayne, Whitley decides to investigate. Ron and Millie hook up while serving as go-betweens. A long-lost flame surprises Lettie with a visit. The couple worked together to publish incendiary material about the South African government, but she rejected his marriage proposal because she could not sacrifice her dreams. Marcus leaves after an argument, but Denise gets him to come back by making a radio dedication in Lettie's name. Marcus explains to Lettie that he is not trying to win her back; he is happily married, and simply wanted to give her a photo of his daughter--whom he named after Lettie.

Denise and Whitley earn lead roles in Maggie's play, a bizarre (and painfully long) adaptation of the story of Adam and Eve. Denise and Whitley vie for the affections of their leading man, who seems to thrive from the attention. When the girls learn that Rick already has a girlfriend, they allow their anger to affect their performances. Although the play ends abruptly after Whitley tries to strangle Rick, Maggie still receives rave reviews. Meanwhile, Dwayne and Ron struggle to design the sets without exceeding their 35-dollar budget.

Whitley enters the Miss Hillman pageant in order to win the approval of her mother, a former pageant winner whom Whitley can never seem to please. Denise decides to fight the elitism of the pageant by convincing Dwayne to enter. The Gilbert Hall residents infuriate Whitley by backing Dwayne as their representantive in Miss Hillman. A fraternity sponsors Whitley; its members, along with other students, constantly mock Dwayne and play cruel pranks on him. Ron and Walter encourage him to save face by dropping out of the pageant. Dwayne refuses, and declares that the harassment he has received has prompted him to reconsider the way he treats women. Although Whitley receives more votes than Dwayne, she loses badly to another girl. Lettie and Denise recognize her disappointment and urge her to live her own life, without worrying about her mother's opinion.

Jaleesa panics at the prospect of making a speech in front of her poetry class. The professor takes pity on her and allows her to substitute a paper for the speech, but suggests that she learn to take risks. Jaleesa stammers her way through the speech; Professor Foster congratulates her on her courage and gives her a B because her content offset the horrible presentation. Denise forgets to pay back some money she had borrowed from Maggie a month earlier. Instead of reminding Denise about the debt, Maggie privately obsesses over the matter. Whitley's humidifier breaks, and she cannot call a repairman without exposing the fact that she has an illegal appliance. Dwayne and Ron help her ship it out for repairs, only to get busted by Lettie. Lettie reveals that she knew about the device; it no longer worked because she had unplugged it.

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.

During the last week of school, Denise accepts a date with Dwayne. She insists that they are only going out as friends, although her roommates note that Dwayne believes otherwise. Dwayne gets reservations at an expensive Japanese restaurant, but has to scramble for a way to pay for dinner after spending all his money on a suit. Whitley becomes despondent when she fails to get an internship in New York, as she must now spend her summer in Richmond with her judgmental mother. Whitley gives Dwayne forty dollars for dinner because she wants someone to find happiness. She shows up at the restaurant in the middle of the date and begins complaining about her problems. She shocks Denise and Dwayne with the revelation that she considers them her only true friends. Although Whitley offers to leave, Dwayne lets her cry on his shoulder and gives advice on how to deal with her mother. Denise is so touched by Dwayne's actions that she begins to see him in a new light. He reads her a poem he had writ

As a class assignment, Maggie and Dwayne must care for eggs as if they were children. Maggie becomes extremely wrapped up in the project, and nearly skips her volleyball game because she is worried about the egg. She finally allows Jaleesa to watch the egg, as she is already babysitting Stevie's son J.T. Jaleesa leaves Whitley in charge while she helps Denise find a calculator, and the egg disappears. Maggie completely freaks out and puts up fliers around the campus. Stevie reminds Maggie that the egg is not a child; she states that real parents can also make their share of mistakes. Although Stevie is a good mother, she once lost track of J.T. in a department store. They discover that J.T. liked the egg so much that he had taken it to his room.

Denise becomes depressed about her grades. To take her mind of her troubles, she calls her brother Theo and asks him to visit for the weekend. Theo, a high school senior, is considering applying to Hillman. He quickly makes friends on campus and has little time for Denise because of his busy social calendar. During an interview, the dean stresses that Hillman is a very difficult academic school. He warns Theo that his fun-filled weekend might be giving him the wrong impression. Denise later reiterates this over dinner; she was an excellent student in high school, and now is having trouble just passing her classes. She wants to take a semester off, but Theo encourages her to tough it out. Meanwhile, Maggie tries to write a letter to her boyfriend.