Whitley has yet to take a basic math course that is required for graduation. She reluctantly enrolls in Col. Taylor's class, and he tries to help her overcome her fear of the subject. Dwayne and Ron clash over finances. Dwayne believes that Ron spends money too freely, while Ron accuses him of being a cheapskate.

Walter and Jaleesa celebrate the anniversary of their first date, but are distracted by conflicts over dorm discipline. Walter allows a shy male student to let his girlfriend stay overnight before she ships out with the Navy. When Jaleesa disagrees and recommends that Quincy be punished, Walter pulls rank on her. They argue during their anniversary dinner, and she winds up storming out of the restaurant. The girls accuse Walter of a double standard; they refuse to vacate Quincy's room until Walter either punishes him or agrees to let them have guys stay over. Whitley demands only the return of her high-powered hair dryer, which has been blamed for many power outages. Walter orders Quincy to appear before the dorm council, and establishes measures to prevent further instances of sexism. Dwayne and Freddie take procrastination to a new level while collaborating on a research paper.

Walter convinces many of the students to volunteer at a community center. Whitley teaches ballet to the children and becomes friends with a young boy named Dion, who claims to be dirt poor. Whitley's wallet is stolen, and she is stunned to learn that Dion was the culprit. He exaggerated the extent of his poverty and took advantage of Whitley's kindness. Whitley does not want to return to the center, but Walter insists that the kids need a positive influence if they are to escape from the streets. Whitley continues with her teaching, and refuses to give up on Dion. Walter's duties keep him away from his bowling team, so Col. Taylor agrees to step in. When he turns out to be terrible, Mr. Gaines and the other team members try to find a way to oust him.

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.

Ron takes a liking to his study partner, Elizabeth; and is surprised to learn that she has a 13-month-old son. He is unsure about getting involved, but quickly bonds with the child. Believing that the boy needs a positive male role model, Ron tries a little too hard to step in and become a father figure. Dwayne arranges a performance by his old friends Heavy D & the Boyz for a charity concert. Whitley, who had hoped to bring in an opera company, organizes an anti-rap protest. She makes a fool of herself by espousing her views to Heavy D, unaware of his identity. Heavy eventually wins Whitley over, and the gang joins him onstage to dance during the show.

Walter wins a free Hawaiian honeymoon from a car wash, so he asks Jaleesa to marry him. Although she is uncertain, she eventually says yes. They plan to wed in two weeks. Jaleesa fears they are rushing and wants to call the whole thing off, but Walter reassures her. During the ceremony, they simultaneously announce that they don't want to get married; Jaleesa believes their interests are too different, while Walter can't fathom a lifetime commitment. They promise to remain friends, even though they will no longer date. Whitley enlists Dwayne's help in planning the wedding. She changes the subject whenever he tries to confess his attraction to her. Dwayne finally pulls Whitley into a kiss, which nearly causes her to faint. He asks her out after the wedding, but she is not ready for a relationship.

Kim and Freddie plan to spend homecoming weekend at Freaknic, a music festival in Washington, D.C. Kim's policeman father calls and forbids her to go to the concert. Kim decides to go anyway, and Whitley has to distract her father when he arrives unexpectedly. When Kim returns, Mr. Reese yells at her and threatens to make her transfer to a hometown school. She insists that she is a responsible 19-year-old who should be allowed to make her own decisions, but her father restricts her to the house for the rest of her vacations. Whitley tries to convince Kim that she is lucky to have someone who cares enough to yell at her, as Whitley seldom received attention from her parents as a child. Ron and Dwayne face a dilemma when each brings a girl back to the apartment.

Whitley is in a foul mood during the holiday season, especially when her mother insists that they fly to the south of France instead of spending a quiet Christmas at home. She coldly rejects Freddie's offer to spend Christmas with her, and refuses to attend the gang's tree-trimming party. Whitley's mother appears to her in a dream and warns that she is headed for the same lonely, isolated existence as Marion. Whitley is visited by the ghosts of Christmas Past, Present and Future (who bear an uncanny resemblance to Mr. Gaines, Walter and Jaleesa). She learns that Freddie will end up staying with Dwayne for the holidays, leading to a romance between the two. Whitley discovers that Dwayne and Freddie will marry, while she will spend her entire life alone. Whitley suddenly gets into the holiday spirit, decorates everything in sight, and asks Freddie to come along to France. However, Marion shows up at the dorm and tells her daughter that she wants to spend Christmas in Richmond. She settle

Dean Hughes asks Whitley to spend the weekend at her house and co-host the annual freshman tea. Whitley considers this a great honor until Freddie is named the other co-host. Whitley hopes to convince Dean Hughes to send her to Europe as Hillman's student recruiter. The dean does not believe that Whitley possesses the necessary skill and discipline for this position. A hurt Whitley insults Freddie and tries to leave, but admits to the dean that she lacks direction. Dean Hughes cheers up the girls and manages to convince Whitley to relax a little. Ron allows a classmate to crash at the guys' place, and the man keeps coming up with reasons to stay. He keeps Dwayne and Ron happy by cooking, cleaning and fixing the toilet. Walter tells them that Earl is a scam artist who flunked out of school. Before they can confront him, Mr. Gaines hires Earl as the building superintendant.

Dwayne's old friend Milt comes for a visit. He believes that Hillman is holding Dwayne back, and encourages him to transfer to the University of Pennsylvania. Milt also recommends that Dwayne distance himself from ""dead weight"" like Ron. Dwayne considers his friend's words, until a talk with Whitley helps remind him of Ron's good qualities and the feeling of family that Hillman holds for its students. He defends the school's academic reputation to Milt. Col. Taylor and Mr. Gaines attend a reunion for U.S. servicemen. Col. Taylor tries to start a romance with a nurse he knew in Vietnam, only to discover that she is a complete mess.

Dwayne struggles with an assignment for poetry class, as the students must compose their own verses. William Shakespeare appears to him in a dream and stresses that his pursuit of a career in math does not mean that he cannot also appreciate poetry. He encourages Dwayne to write about something for which he feels passion. Whitley reads Dwayne's beautiful poem and believes that it is about her. She is angry and embarrassed when the rest of the class interprets the poem differently; it is actually about Dwayne's love of mathematics. Freddie juggles dates with environmentalist Livingston and Ron's handsome friend Ernest. Although neither relationship is exclusive, she feels guilty until she sees Livingston with another girl.

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

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.

Whitley meets Julian, an attractive exchange student from Georgetown who is part of Hillman's anti-apartheid group. Kim receives a scholarship that will solve her financial problems and allow her to gain work experience in a lab, rather than flipping burgers at the Pit. Unfortunately, Freddie discovers that the company funding the scholarship is a subsidiary of a corporation with investments in South Africa. Julian proposes a boycott; he angers Whitley by recommending that Hillman cut all financial ties with the corporation, as this would cost Kim her scholarship. Due to her father's health problems, Kim would have to work two jobs to stay in school. A young man from South Africa argues against the termination of scholarships, because he feels that the success of African American students serves as a beacon of hope to black South Africans mired in poverty and oppression. Kim decides to turn down the scholarship anyway. Whitley accepts a date with Julian.

Whitley plays matchmaker for Dwayne and a beautiful coed in the hopes of convincing him to move on. However, she becomes extremely jealous and tries to sabotage the couple's date. Dwayne and Whitley try to establish some ground rules in an attempt to save their friendship. Walter angers Jaleesa by claiming that women cannot play poker. He bets that she cannot teach Freddie how to play, while Jaleesa challenges him to turn novice Kobie into an accomplished player. Neither apprentice picks up the game, but Jaleesa literally beats the pants off of Walter.

A lovesick Dwayne convinces Walter to let him tag along on a recruiting trip to North Carolina, where he is trying to sign a high school basketball prospect. Walter gets pulled over for speeding and is arrested because of his unpaid jaywalking tickets. Alvin Dix, the young man Walter is recruiting, has to bail him out of jail. Alvin shows little interest in Hillman because he wants to play for legendary coach Cap Connors. Walter, who played for Connors, tells Dwayne that the coach cares only about basketball and discourages players from getting a good education. Walter and Dwayne cause a melee at a restaurant when they mistake Connors' wife for a groupie, as the coach had used attractive women to recruit players in the past. Alvin eventually realizes that he and Connors have philosophical differences, so he decides to consider Hillman. Dwayne causes problems throughout the trip because he keeps seeing Whitley's face on every woman and deer. Jaleesa engages in another battle of the sexe

Whitley has trouble finding a job for after graduation, while Jaleesa mulls several offers. Ron's sister Rachel, who is staying with Whitley and Kim during a campus visit, suggests the career of art buyer. Whitley becomes very excited about this idea and uses her mother's connections to set up an interview. She fails to get the job because she lacks financial experience. Whitley decides to stay at Hillman another year and take some business courses. Rachel grows tired of Ron's overprotective behavior. Dwayne hosts an incoming freshman, a lecherous math enthusiast who reminds everyone of a younger Dwayne.

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.

Walter learns that Kim is working all night at a funeral parlor to cover her expenses. He enlists the help of Whitley and Freddie to come up with a plan to help her out. Whitley and Freddie buy gifts for Kim and get everyone to stuff the tip jar at the Pit. Kim realizes what they are doing and becomes very angry, as she doesn't want to be a charity case. Mr. Gaines finally convinces her to overcome her pride and accept a loan from his wife and him, which she can pay off after becoming a doctor. A director approaches Ron and Dwayne at the basketball courts and asks them to appear in a vitamin commercial. They agree because they are having trouble paying the bills. The guys believe that they will receive fame and adulation, until they discover that they must play two-on-two against a pair of retired NBA all-stars.

Col. Taylor is the guest of honor at a campus roast. Frank Benning, a man from his first platoon in Vietnam, comes in to serve as the surprise guest speaker. Col. Taylor feels very uncomfortable; he believes that he committed an error on the battlefield that cost Frank his leg. Frank tells a different version of events in his speech. He insists that Col. Taylor is a great leader whose bravery saved everyone's lives. Ron tries to organize the dinner while fretting about the impending selection of the ROTC's Cadet of the Year award. Dwayne bets Whitley that she cannot go a full day without flirting.

Dwayne, Ron, Kim, Freddie and Ernest head to Devil's Island, South Carolina for spring break. Whitley joins them at the last minute after Julian has to cancel their vacation due to a job interview. Ernest has big plans for Freddie, but passes out drunk. Ron tries to put the moves on Kim. A pair of murderous drug dealers searches the gang's van for a missing duffel bag. Dwayne and Ron discover money and drugs in the bag and try to go the police. Freddie and Kim meet the drug dealers on the beach and flirt with them, unaware that they are criminals. Dwayne and Ron return to the house after missing the ferry. Dwayne overhears the men threatening to kill him and tries to make a break for it.

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

Dwayne is selected for Phi Beta Kappa, and his mother comes to town to watch his induction ceremony. Julian tells Whitley that he wants to ask her something important during their next lunch date, leading her to believe that he plans to propose. He instead asks her to spend the summer with him in Washington, D.C.; he will get her a secretarial job with his company. When Whitley insists on attending summer school and taking an internship, Julian accuses her of being sheltered. Whitley goes to Dwayne's apartment in search of advice, and mistakes Mrs. Wayne for a maid. Dwayne tries to cheer Whitley during a dinner party organized by his mother; he admits that Whitley is spoiled, but believes that Julian should give her some credit for setting her sights on a career. Mrs. Wayne warns her son that Whitley is trouble. Whitley gives Dwayne a gift and thanks him for always being so supportive. Mrs. Wayne asks her to join them at Dwayne's induction ceremony.