During Presidents' Weekend, the gang goes to Palm Springs, where Dylan and Brenda plan to meet at a hotel for some time alone. But Brenda forgets the name of the hotel where she's supposed to meet Dylan. Meanwhile, David, wanting to fit in with the gang, ditches Scott and their trip to Magic Mountain to take Steve, Kelly and Donna to his grandparents' house, which is supposed to be empty. And Brandon stays home to help Nat at the Peach Pit, and discovers a secret that an apparently sarcastic boy named Curtis has been hiding.

Jim sets a lonely Brenda up on a blind date with Stuart Carson, the son of his business associate and both he and Brenda hit it off. Dylan decides to buy a new car, regardless of the price. Due to his late night schedule, David causes problems with Kelly and Donna over his lack of housekeeping. Kelly tells Dylan that they should start seeing others as a result of her growing relationship with John Sears. Meanwhile, Andrea finally loses her virginity when she and Dan move beyond being "just friends."

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.

When their wedding plans become too much of a hassle, Stuart convinces Brenda that they should elope to Las Vegas. After Brandon finds out, he gets the rest of the gang to drop what they are doing and they all fly out to Vegas to try to discourage Brenda and Stuart from their marital plans. Meanwhile, Laura wants to see more of Steve, who tries to keep things between them under wraps. On other personal fronts, Brandon continues to try to keep Lucinda distant who continues to flirt with him every chance she gets. Donna continues to try to resolve the continuing feud between David and Kelly.

Donna tries to make up with David, whose increased drug use turns her away. David also steals $150 from his father to buy more amphetamines for himself. When his drug dealer is arrested later, he finds himself in possession of a huge stash of narcotics and calls on Dylan for help. Meanwhile, Jesse and Andrea meet with her grandmother to get her blessings before their wedding and reception at the Peach Pit. A dangerous affair begins between Brandon and Lucinda, who shows her true colors when she starts teaching her anthropology class of human sexuality and preaches the need for multiple partners, seeing sex as her personal weapon. Brenda gets a surprise visit from a long-absent Stuart on Valentine's Day.

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.