When Kelly's mother Jackie, divulges the secret that she's pregnant, misunderstandings and grapevine talk between Kelly, David and Donna threaten to end the relationship between her and David's father Mel. Meanwhile, Nat takes Brandon, Steve and Andrea to the racetrack to bet on some horses due to Andrea's "power" to see the winner, and Dylan plans a special Valentine's Day for Brenda, of donating blood.

Brenda, Kelly, and their mothers Cindy and Jackie, as well as Donna and Andrea enjoy a good life for the weekend at a posh health spa, until Brenda overhears a conversation about Kelly's stepdad's unfaithfulness to Jackie. Meanwhile, Jim questions his mid-life crisis with his secretary Dottie and a best-selling author on the subject. Dylan finds two separate fantasies about a future with Brenda and Kelly not fulfilling. Also, Brandon starts gambling on basketball games with Nat's bookmaker Duke.

After dissolving the trust fund, Dylan, Jack and Christine enjoy the good life together on a friend's yacht at Marina del Rey. But they are all under observation by unidentified men. Meanwhile, finances force Kelly's mother to put their house up for sale. Brenda, Donna and Cindy take a class in self-defense. Brandon continues gambling and starts losing money totaling $500 which makes Duke rather angry, but lets Brandon slide his losses. Andrea get invited on a date with Jordan. Also, David meets with Serge Menkin, his new recording manager, who insists that David record some different rhythm tracks.

Gambling addict Brandon multiplies his addition by hiring a school bookie, Jeff, in order to pay off $1,500 of losses to Duke who's now out to get Brandon. Meanwhile, David finally realizes the true nature of the music industry when Serge continues to ignore his hip-hop material and forces him to record a repetitive, syrupy ballad. David goes along with it, but Curtis Bray does not like the new tune and outright terminates David's recording contract. Finally seeing the egotistical, two-faced shark that Curtis Bray really is, and the self-serving hack Serge is, David leaves Icon Records and goes back to apologize to Steve for the way he treated him. Kelly's eating disorder worsens when she starts taking diet pills. Also, Andrea tries to ease Dylan's depression over his father's murder by asking him if she can do an editorial on him.

Steve begins an internship at a talent agency and later tries to comfort his discouraged supervisor, Tammy Kane, after she is dismissed from the agency. Donna covers for the new Rose Queen, Lisa, at her convenience-store job in South-Central L.A. and feels sympathy for a ghetto boy she catches shoplifting. Donna forces Joe to drive her over to the boy's house and learns that the boy, Isaiah, and his two siblings are not supervised at home. Meanwhile, Susan learns more about Brandon when his addiction to gambling resurfaces during a casino-night fund raiser at the After Dark. Also, Valerie and Kelly vie with each other to buy a portrait to pose for Colin.