Steve's so-called "harmless prank" of streaking with his fraternity pledges for Spirit Week lands Brandon in trouble. He refuses to give a video tape of the event to Chancellor Arnold, knowing it will incriminate Steve, while Tracy decides on a crafty plan to get Brandon off the hook. Meanwhile, Donna becomes chairperson of the rush committee for ALPHA sorority and lobbies to get a female jock, named Dani, accepted. Kelly takes a sickly Jimmy on a religious journey to explore his Jewish roots before he dies. David returns to school at California University, but finds all the classes he wants full, and he even has a run-in with Olympic champion gymnast Kerri Strug. Also, Kenny shows Valerie his new apartment for her to live in, but Valerie becomes angry and upset when he breaks a dinner date with her in order to go out with his wife and young son whom he continues to hide his tryst from them.

On Valentine's Day, Donna's former beau, Cliff Yeager, shows up and causes concern for her and David. Meanwhile, Valerie's mother, Abby, whom she can't stand, arrives in town from Buffalo for a visit and asks Val for financial support. Steve commits yet another error with Clare when he decides to take up smoking pot with Dick Harrison. Chloe makes her singing debut and David get to be the MC for Luther Vandross at the Peach Pit After Dark's Valentine's Day party. Kelly continues dating Tom, and an unhappy Valerie tries to halt the union. Also, Tracy gets a big surprise from Brandon when she mistakenly thinks he bought her an engagement ring.

Brandon, Steve and Dick are partnered together for a three-man basketball team at CU. But that night, Steve and Dick's marijuana habit takes a turn for the worse when Dick suggests heroin and eventually dies from an OD at the After Dark. Meanwhile, Donna wavers between David and Cliff, who try to get on the good side of her parents. Gigi Crane, a magazine writer, starts hanging out with Valerie to get a story about L.A.'s cool people. Kelly and Clare pose as Russians to do some flirting with two other guys during a weekend trip to Palm Springs.

After Brandon breaks up with Tracy, Valerie's meddling jeopardizes his future with Kelly when Val sends Kelly a phony letter from the departed Dylan to test her true feelings for Brandon. Meanwhile, Donna persuades Felice to accompany her to the KEG/ALPHA spring campus talent show, where she gets increasingly worried when a former boyfriend of Felice's (from 'Things to Do on a Rainy Day') shows up to accompany her. Also, Clare takes the stage to sing her favorite song due to a suggestion from Steve, who thinks the idea's all wet when he hears her awful singing voice during rehearsals.

David takes Donna on a one-night trip to New Orleans in an attempt to sleep with her, which also delays Donna's presentation of her business project the very next day to her stern teacher, Professor Langley. In Beverly Hills, the relationship between Steve's mother and Clare's father becomes strained during a TV historical awards dinner, when Steve's self-obsessed mother once again lets success go to her head, which also strains the relationship between him and Clare. Meanwhile, Brandon attempts to nurse a flu-stricken Kelly and Valerie back to health, who re-live to each other how they became hard-core enemies two years ago which involved both of them pursuing Brandon. At the end, Valerie secretly meets with a certain Derrick Driscoll, who works for Kelly's father, to ask about a possible investment plan.