Whitley accepts a date with the persistent Ron in the hopes of making Dwayne jealous. She leaves a series of answering machine messages in which she repeats the time and location of the date, believing that Dwayne will show up. Ron ignores Dwayne's warning and insists that Whitley really likes him. After they have a good time at a club, Whitley feels guilty and admits that she was trying to get to Dwayne. Ron accepts her apology and says that he is happy to help, as he cannot stand Kinu. Ron pleads for a kiss at the end of the evening, and Whitley pecks him on the cheek. When Dwayne comes out of his apartment, she pulls Ron into a long liplock. Freddie hopes to get into a class taught by Professor Randolph, a respected authority on African American history. Professor Randolph asks students to write an essay explaining why they would like to enroll, but Freddie impresses him with a performance art piece. Freddie's cousin Matthew, who is white, comes over from Avery College to take the c

Whitley's father comes to town and takes her to dinner. He announces that he is fed up with her exorbitant spending habits and takes away her credit cards. He will now only cover her tuition and basic living expenses. Whitley begs Jaleesa to let her continue living in her apartment, although she cannot quite cover her share of the rent and utilities. Whitley bemoans her plight and claims that everyone has abandoned her. Kinu catches Dwayne trying to console her. Freddie believes that Kim is studying too hard for the practice medical school boards. She tricks Kim into taking a break and coming to Ron's frat party. Kim plays a practical joke on Freddie; she pretends that she bombed the test because of exhaustion, then reveals that she actually scored 88 out of 90.

Whitley decides to try out for the academic decathlon, as the winning team will receive $1500. Although Dwayne and Ron make fun of her, Whitley proves to be quite knowledgable and makes the team. She and Dwayne are disgusted to learn that they must be partners. During a late-night practice, they start wrestling and fooling around and end up kissing passionately. Whitley overhears Dwayne assuring a jealous Kinu that he has no interest in Whitley. Whitley files her nails during the game, leaving Dwayne to carry the team singlehandedly. Dwayne apologizes and convinces her to play, but they barely lose to Kinu's team. After Dwayne and Kinu leave to celebrate, Whitley declares, ""You may have won the prize, but I will get the man."" Kim turns down a date from Matthew, telling Freddie that he is strange and she isn't strong enough to deal with an interracial relationship. Freddie argues that Kim doesn't want a social life because it might interfere with her routine. Kim asks Matthew out for co

Dwayne falls apart in the aftermath of his kiss with Whitley. He cannot sleep due to recurring nightmares, and lets the apartment turn into a pig pen. Kinu becomes extremely bossy and territorial; she argues with Ron (who is tired of her constant presence at the apartment), then tries to bar Whitley from a party honoring Dwayne's and her six-month anniversary. Ron, hoping to drive Kinu over the edge, hires cash-poor Whitley as a housekeeper. Dwayne's mother arrives in the midst of the women's sniping because she had sensed that something was wrong with her ""chipmunk."" Mrs. Wayne doesn't like Kinu any more than she does Whitley, so Whitley tries to take advantage of the situation by buttering her up. Kinu finally snaps and takes it upon herself to fire Whitley. Dwayne admits to Kinu that he cannot shake his feelings for Whitley. They decide to break up.

As her marketing project, Whitley organizes a ""Men of Hillman"" calendar. Dwayne is offended when she doesn't ask him to participate; she doesn't consider him brawny enough. She finally lets him pose for the calendar, but superimposes his face on someone else's body. Ron finds himself juggling three Valentine's dates, as one of his girlfriends gets the night off from work and another returns early from an out-of-town trip. When he comes clean with the girl he likes the most, she is not as understanding as he had hoped. Jaleesa and Col. Taylor spend Valentine's Day together, until his bad back cuts the evening short. Matthew hopes to ease Kim's discomfort about being seen with him in public. Mr. Gaines tries to placate his wife, who complains that he is not as amorous as he was at one time. Freddie raves about a secret admirer, and is disappointed to find that it is Terrence.

Matthew arranges for some friends from the National Theatre of the Deaf to perform for the children from the community center outreach program. Kim feels embarrassed by Matthew's free-spirited behavior, which she considers too silly. Matthew insists that his passion for acting is as great as Kim's devotion to medicine, and offers the opinion that art is just as important as science. Kim cares about Matthew, but is uncertain about their relationship. She observes Dwayne and Whitley's example and decides that they can learn to appreciate each other's differences. Everyone teases Whitley about her tendency to run off at the mouth. Dwayne bets that she cannot go a full day without speaking.

Shazza Zulu, a student in his sixth year of undergraduate work, publishes a book discussing the sexist behavior of men at Hillman. The women take his words to heart; they get really worked up and decide to boycott all men. The men respond with a boycott of their own. Everyone gets upset with Dwayne and Whitley for refusing to take part, and Whitley's friends try to convince her that Dwayne is fooling around with the female students he tutors. After a food fight breaks out at the campus movie theater, Dean Hughes calls a summit to get the two sides to work out their differences. The students turn against Shazza, who insists that he is trying to promote harmony. He singles out Kim as someone who has turned against her race by dating a white man. She tells him off and storms out. Ron, who had earlier expressed a similar sentiment, apologizes to Kim and admits that he was jealous.

Whitley gets a job as an assistant art buyer for E.H. Wright Industries. She attends an auction in Washington, D.C. as an observer. When her boss steps out to take a phone call, Whitley disobeys her wishes by bidding on a painting from a promising young artist. Whitley fears that she will lose her job, but the painting turns out to be a great investment. Although her boss disagrees with her tactics, she applauds Whitley's intuition and enthusiasm. Freddie's new philosophical radio call-in show fails to attract interest because no one has any idea what she is talking about. She becomes a big hit after she assumes the persona of Jamaican-born ""Mother Eartha"" and distributes advice to her listeners.

The community outreach program loses funding after a corporate buyout, so Walter organizes a three-hour telethon to raise the $15,000 it needs to remain in operation. Jaleesa, Kim and Kinu sing, and Mr. Gaines tap dances (with musical accompaniment from Col. Taylor). Whitley's tribute to Josephine Baker falls apart when her male dance partners begin fighting over her. Dwayne begs for a chance to perform stand-up comedy, but suffers from stage fright. Although the telethon enjoys some initial success, the phones stop ringing during the final hour. The program only raises about $7000. Walter assures the children that he will find a way to come up with the rest of the money.

Whitley plans to sleep with Dwayne for the first time on his birthday. The public speaking professor assigns the students to write their own eulogies. A young woman named Josie stuns everyone with her speech, in which she reveals that she contracted AIDS through unprotected sex in high school. Gina and Terrence display their ignorance about the disease and are afraid to be around Josie. Kim and Mr. Gaines defend her and advise the duo to become more informed. Ron worries that he could fall victim to AIDS because of his history of casual sex. He and Dwayne decide to undergo HIV testing. Whitley, still shaken by the news of Josie's illness, decides that she just isn't ready for sex.

Walter announces that he is leaving Hillman to take a job at a community center in Philadelphia. A roast is organized to give everyone a chance to say goodbye to him. Ron learns that he cannot graduate because he failed to take a European history course. Walter lobbies the dean on his behalf and convinces him to let Ron take the final. Although his friends help him cram for the test, Ron cannot learn enough in one night to pass the difficult exam. He wants to drop out of school, until Walter reminds him of his father's probable reaction. Kim receives a grant to study medicine in London over the summer. She and Matthew must head their separate ways, as he is going to spend the summer with an acting company in Seattle.