Brandon and Kelly continue to hide their relationship from Dylan, but the truth is always bound to come out somehow. Brandon decides to tell Dylan about him and Kelly, but Brandon chickens out when he sees Dylan drinking again and in a bad mood. At the same time, Dylan confirms that his entire financial base has been cleaned out by Kevin and Suzanne's scam, but he naturally keeps his crisis to himself. Meanwhile, Donna plans to take the semester off to participate in a debutante ball. Kelly however rightfully suspects that Donna is hiding behind Felice, in order to move away from David. Dylan begins giving everyone a hard time: he crashes Felice's charity event and makes a scene after being tipped off by Nat about Kelly and Brandon. He then goes to the night club where Jesse is working nights and asks for a drink, but Jesse turns him away. Dylan then meets a prostitute at the club and takes her home with him where Kelly, wanting to talk with Dylan, later walks in on them. Both Brandon and Donna confront Dylan about his actions and he seems to be listening to them, but ultimately decides to not return to college and pursues more self-destructive behavior. With Jesse working nights and studying in law classes during the day, Andrea tries to arrange more time to look after baby Hannah.

Brandon wins the election for student body president, but Josh's death hangs heavy on him. Alex tells Brandon he's contesting the election, using Josh's death as leverage to unseat Brandon in order to take the title of president for himself, while Brandon is surprised and touched to learn Josh deeply admired him and resolves to fight for his office in Josh's memory. Meanwhile, Donna finally meets a man, a KEG frat member named Griffin Stone that her mother sets her up with, that makes her forget David, who meets Clare and begins dating her. Also, Valerie continues dating Steve while seeing Dylan behind everyone's back.