Dylan considers buying a gun after his new car is stolen from him at gunpoint. Meanwhile, Brandon's sociology professor Corey Randall asks him to tutor the university's basketball star, D'Shawn Hardell; Andrea and Dan mull over going public with their affair; Brenda and her parents are invited to lunch at Stuart's parents' house in Bel Air as Brenda and Stuart's romance really takes off.

Cindy and Jim throw a party for their 20th wedding anniversary. As Stuart and Brenda's affair grows, he proposes marriage and she willingly accepts. Meanwhile, Brandon falls for an anthropologist grad student named Lucinda Nicholson. A paranoid Dylan buys a gun from a street dealer and almost shoots Brandon. Andrea tells Kelly that she has doubts about her affair with Dan after he tells her about his non-belief in marriage; then Andrea meets Jesse Vasquez, a charming Latino barman, at the party. Mel asks David to look after baby Erin while he heads off to Mexico with his girlfriend.

Brenda is bothered when Stuart tells her that his parents want her to sign a prenuptial agreement; Jim also finds out about Stuart's prenuptial papers and asks Dylan to look into Stuart's background. Meanwhile, David and Kelly grow more hostile to each other when they are caught in the middle of Mel and Jackie's custody battle for Erin. On his first dinner date with Lucinda, Brandon discovers that she is married... to his sociology professor. Guilt plagues Steve he does a favor for Sears and his frat buddies to bed blind date Laura Kingman, a professional college dancer.

After Steve breaks up with Laura, she tells Kelly and others that he date-raped her the night they were together to get back at him. Meanwhile, Kelly learns Sears true sexist colors and rejects him, but he too doesn't take it so kindly. Dylan tutors Brenda in poetry which brings them to a disagreement. Also, Brandon's relationship (or lack of it) with Lucinda takes a dangerous turn when D'Shawn finds out and threatens Brandon to take his history mid-term for him or he will tell Professor Randall of his suspicions. When Lucinda insists to Brandon that he should take D'Shawn's tests, Brandon reacts stressed and hits the road.

Strange dreams contemplate Donna to fulfill David's dream to sleep with her on their second anniversary together, until her parents show up for a surprise visit. Meanwhile, Brandon returns from San Francisco where he learns about the Steve's botch break-in, who finds himself left in cold after Mike Ryan and the rest of the frat members reject him. Only John Sears remains sympathetic to Steve and tries to help. But when Brandon learns and relays to Steve that the campus police were anonymously tipped off to Steve's break-in, Steve realizes that Sears had set him up. In the meantime, Brandon plays hardball with the corrupt Professor Randall to drop the break-in charges against Steve by threatening to go public about him rigging test scores for D'Shawn and other basketball stars to they can play basketball for the university. Elsewhere, Andrea falls deeply in love with Jesse. Also, John Sears continued wooing of Kelly only pushes her back to Dylan.

David's work and study schedule begins to take a toll on him when mid terms come around, leading him to start using crystal meth. His erratic behaviour worries Donna and Kelly. Dylan wants to help Suzanne with her financial troubles by giving her $10 000 but Jim urges Dylan to let him do a background check on her first. Steve decides to take his suspicions about John Sears to their fraternity chapter president. Brandon continues to tutor D'Shawn in sociology but still feels that Professor Randall is giving him preferential treatment. During a basketball game, D'Shawn sustains an injury that he fears will impact his future career prospects. Andrea learns from her new RA that Dan Rubin has transferred to another dormitory.

Brandon uses Kelly as his date at a university social event to shield his affair with Lucinda from Josh Richland, a snooping student reporter from the Condor determined to dig up any dirt on Brandon. Meanwhile, Brenda and Stewart travel to Palm Springs where they find big complications from a small mistake Brenda makes which leaves them stranded in the desert, where Stuart fumes over and it resulting in her finally breaking off their engagement for good. David rents a piano as a new hobby while Kelly moves back in with him and Donna. Also, Andrea lets Steve use her dorm room after he can't stand living at the KEG house.

When the rest of the gang takes off on a ski weekend, Brenda stays behind and discovers an old diary that belonged to a young woman who once lived in the Walsh house with her parents and brother in the late 1960s, in which Brenda imagines herself and the gang as the girl Wendy and the gang as her hippie friends.

While working with Kelly to recruit guys for the "Men of CU" beefcake calendar that they're working on, Donna goes on a spontaneous date with D'Shawn just to make David jealous when she finds him flirting with his blind piano teacher Holly. Meanwhile, Steve sees no reason to keep the secret that their frat president, Mike Ryan, is gay despite being sworn to secrecy.

In the two-part season finale, Brandon goes to Washington D.C. as a part of the college task force to meet the president. Kelly follows Brandon to Washington to get him out of a jam when Clare and Lucinda arrive at the hotel to pursue him. At the CU Mardi Gras, David impresses pop star Kenneth "Babyface" Edmunds, and his recording manager Ariel with his keyboard music and Donna catches David in a very compromising position with Ariel. Steve runs into Celeste who's now with John Sears. Kevin and Suzanne get married in a semi-formal ceremony where he persuades Dylan to cut out any outside investment in their business offer. Jim becomes angry at Dylan for making such a rash move and Dylan fires Jim as his financial holder. Dylan then goes to a bank and gives Kevin full power-of-attorney control over his money, unaware that Kevin and Suzanne have had a hidden agenda for Dylan's inheritance all this time. After her major success in the CU play, Brenda gets a scholarship offer to study acting in London and she pays a visit to Dylan's place before leaving. Also, Andrea and Jesse experience the joys and fears of parenthood after their daughter is born.

Donna announces to the gang that she has decided to move to Houston to be a débutante. But Kelly eventually learns that Donna still emotionally fragile since her breakup with David and she's hiding behind her mother just to avoid running into him. Dylan also finds out that his entire bank account is cleaned out by Kevin and Suzanne's scam, but alienated with life and embarrassed and ashamed at himself for what happened, Dylan keeps his financial problem to himself. Meanwhile, Brandon decides to tell Dylan about him and Kelly, but chickens out after seeing him drinking again. Later, at a banquet for Donna's, Dylan crashes the party and creates an ugly scene after being inadvertently tipped off by Nat about Brandon and Kelly. Dylan then goes to a nightclub where Jesse is bar-tending and tries to get a drink, but Jesse turns him away, and Dylan also picks up a prostitute at the bar. When Kelly comes over to Dylan's out to talk to him, she finds him with the scantly clad prostitute. When Donna's mother criticizes her behavior by accepting a dance with D'Shawn, she decides to face up to Felice and stay in Beverly Hills. The university's day-care program leaves Andrea wanting to spend more time with her baby. Also, Brandon is reunited with Josh Richland who offers him a chance to run with him for campus office.

Brandon runs for vice president alongside Josh and does great when he steps in and gives a speech in Josh's place. Their campaign is threatened, however, when Alex Diaz - their opponent's campaign manager - uncovers the unpublished article that Josh wrote about Brandon the previous year, detailing Brandon's tutoring of D'Shawn and alleging that Brandon took tests for D'Shawn. Donna asks Clare (now attending C.U. as a sophomore) to move into the beach apartment in David's place, but Clare brings a bad snoring habit with her. Meanwhile, Valerie secretly decides to pursue Dylan after finding Brenda's mementos of him in the Walsh's garage, and hides her connection to the Walshes from him.

Brandon and Dean Trimble are caught in the middle of a conflict when several Jewish students, including Andrea, protest the scheduled campus appearance of a controversial, anti-Semitist, African-American orator, in which the demonstrations and near-riots disrupt Kelly's photo shoot for the magazine. Meanwhile, Donna plans a party for Ray's 25th birthday. In the hospital, Dylan spends the time talking with his mother Iris, while his drug dealer pays an unexpected visit and threatens him not to tell the police about their business.