Brandon is given the request of escorting Lily, Joan's wild and crazy teenage daughter, prior to hers and Nat's wedding, which has a sudden change of venue when a very pregnant Joan goes into labor. Meanwhile, Kelly volunteers to do community service work at an AIDS hospice and befriends Jimmy Gold, a gay AIDS patient whom she is assigned to work with. David moves in with Mark at his house in the Hollywood Hills and later becomes discouraged when he learns of MZA's decision to dismiss him. Also, Valerie is frustrated when Kenny's wife suddenly shows up, disrupting their romantic plans.

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.

Kelly delights in telling Brandon about Valerie's pregnancy and abortion, and also shares her doubts about Val's story. Brandon goes to see Kenny, who portrays himself as the innocent victim caught in the web of an evil vixen. He tells Brandon that he paid Valerie $100,000 to stay away. Brandon threatens to throw Val out of the house unless she returns the money. Valerie plans to move out, but instead returns the money following a talk with Tracy. She confesses to Brandon that she was never pregnant, and insists that she cannot live up to his moral expectations. Mel, worried by David's newfound wealth, asks Donna to keep an eye on him. David goes on a wild spending spree, and later shows up at Donna's apartment in the middle of the night after swimming in the ocean. David offers to help out the financially strapped Valerie by purchasing half of the club. Steve impresses Clare with his dedication as he trains for the crew race. His team barely loses, but Clare decides that she wants him back. Kelly comes clean with Mark about her past drug problem.