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.

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.