Dylan enters a rehab center after all of his friends conduct an intervention. Valerie and Clare, left out of the intervention, spend the day shopping and bonding with each other. But after one day, Dylan runs away from the clinic with a little of Valerie's help. Dylan then alienates Valerie more with his continuing drug use and attitude in which she walks out on him for good. Kelly gets a modeling offer from Seventeen magazine. Meanwhile, Ray has dinner with Donna's wary parents Felice and John. Also, David and Clare's homemade video of their lovemaking disappears and turns up in the home of Donna's parents.

Donna's snobbish mother, Felice, puts Ray's feelings for her daughter to a test by offering him money to stop seeing her, while Ray's alcoholic, chain-smoking, redneck mother, LuAnn, goes Christmas shopping with Donna. Differing family traditions cause tension between the Catholic Jesse and the Jewish Andrea. Clare introduces David to her father during a faculty Christmas party who finds common ground with him over their love of music. Meanwhile, Dylan goes to his old friend, Christine Pettit, from the FBI to help him find his stolen money. Unable to help Dylan, Christine then contacts an alcoholic, former FBI agent-turned-bounty hunter/private investigator, named Jay J. Jones (Jonesy), who contacts Dylan on Christmas Day and offers to track down his money in exchange for getting a full share of it. Brandon is left alone to care for the recovering Kelly when Jim and Cindy leave town to visit Brenda in England and Valerie leaves to visit her mother in Buffalo. Also, Nat hosts a special holiday feed-the-homeless dinner at the Peach Pit.

Steve tries to secure the R&B group "Jade" for a Valentines Day telethon at the Peach Pit After Dark. Meanwhile, Brandon coaxes Kelly away from Professor Finley and his work at his newly opened commune, but only for the moment. After moving out of the Walshes and into a hotel suite, using some of Dylan's money, Valerie comes onto Ray who's having problems with Donna and pressures him into an affair. Ray's mother, LuAnn, figures out that Ray cheated on Donna when he doesn't come home after that night, and covers for him when Donna comes calling asking of Ray's whereabouts. Also, Andrea with Jesse meets Peter and his wife, but that doesn't disrupt their feelings for each other.

When a rainstorm hits Beverly Hills for the week, Andrea gets a job at the hospital where Peter works just to be near him. Valerie refuses to accept a "no" from Ray in response to a relationship with him. Meanwhile, Dylan goes undercover as a new Finley follower at the commune to spy on him and Kelly, while Brandon questions Chancellor Arnold and then seeks out a former Finley follower to speak to Kelly about Professor Finley's true racial and unethical ways.

An unseen psycho, who may be the creepy grad student Lenny, creates a crime wave on the CU campus which includes the rape of a coed, worrying everyone. Meanwhile, Ray decides to leave town after Valerie buys the Peach Pit After Dark from Steve's father for her own use. Peter tempts Andrea to stay out late at the hospital with him, so she gives in to his requests to sleep with him. Also, Dylan is tempted by Valerie to fall off the wagon again. Seeking answers to his path in life, Dylan tracks down and finds his rehab friend Charlie Rollins, a motel owner, where Charlie tells him his idea of writing a movie screenplay to make money and asks Dylan for a little help.

Kelly finally becomes a cover girl on Seventeen magazine, but hesitates to continue modeling due to her fire burn scars. While coping with her newfound stardom, Kelly learns that she has a new admirer: the horribly scared Alison from the fire that night. Ray returns to Beverly Hills and to a bravo return appearance at the After Dark. But Ray's mother LuAnn, in an intoxicated state, ends up tipping off David and Clare about his unfaithfulness to Donna with Valerie. After David and Clare confront Ray, and then Valerie, they decide not to tell Donna to avoid hurting her feelings. Meanwhile, Andrea thinks about her future after Jesse is offered a law position in Idaho. Also, Dylan continues talking with Charlie about the correct script for themselves.

The gang goes to Palm Springs for the national KEG/ALPHA fraternity/sorority convention, where Steve tries to find the perfect woman for himself after he rejects the blind date his father sets him up with. But Steve gets more than he bargained for when he meets a shady women named Elle. Kelly spends a day shopping with Alison in which David and Clare misinterpret their relationship as something else. Jim and Cindy put their house up for sale before moving away to Hong Kong. Meanwhile, Donna brings Ray along to make up with him, but later regrets it when he injures her during a fight, while he manages to stay on the good side of her mother. In another part of town, Dylan and Charlie meet with Tom Rose, a mobster-type businessman as a potential backer for their film who agrees to finance their movie, but only if Tom's beautiful, but untalented mistress, gets the lead role.

Joe's assault and battery trial begins where Donna is caught in a lie on the witness stand, and Brandon gets a national byline for his coverage of the trial. Meanwhile, the sociopath Valerie once again puts her manipulative skills in action when she tells Colin and Susan about Brandon and Kelly's romantic liaison at Thanksgiving to break them up, while Kelly sees a different and kinder side to Colin when they spend time with her sister Erin.