Amanda and Peter continue to fight constantly. Peter decides to stay with Michael and Kimberly for a while. He spends one night on the McBrides' couch after drinking heavily. While he is sleeping, Taylor stares at him and talks about how much she missed him. Amanda rents the restaurant for the night and reconciles with Peter. When Jake refuses to respond, Alison confronts Jane about her loony behavior. Megan insists that Michael doesn't need to know anything about her. Kimberly undergoes an MRI to determine the cause of her headaches. Kyle comforts Sydney after she has a disastrous blind date with an acquaintance of Samantha's. Matt expresses a romantic interest in Dan.

Taylor reveals that she is the younger sister of Peter's late wife Beth. She hangs out with Peter while Amanda is away on a business trip, and helps him pick out a ring for her. Samantha gives Billy the brush-off after he laughs about Jake and Alison's problems. She begins dating Craig. Michael learns that Megan is a prostitute. Kimberly is diagnosed with an inoperable brain tumor. Michael vows that he will take care of Megan. After Michael leaves Megan's house, Kimberly arrives to discuss their ""arrangement."" Jake confronts Jane and emphasizes that their relationship is over. She realizes that she was taking her anger toward Richard out on him. Matt gives Dan the credit for his improvement at school.

Michael signs the divorce papers, and marries Megan during their trip to Las Vegas. Peter learns that Kimberly has a brain tumor, and breaks the news to Michael. Jane is robbed at gunpoint at the boutique. Sydney calls her parents, who come to Los Angeles to comfort Jane. Jane decides to go home to Chicago for a while, and agrees to stay in touch with Sherry. Sherry and Ed get engaged. Jane turns the boutique over to Syd, and says goodbye to her sister and friends at the airport. Alison learns that she is pregnant. Amanda gets Craig drunk during an evening out. He reveals that Arthur murdered Craig's grandfather when Craig was twelve. Matt agrees to move in with Dan. When Jake and Billy become suspicious of Matt's black eye, Dan accuses Matt of betraying him. He assaults him again. Sydney pushes Carter away when he still cannot find time for her. His assistant, Walter, tries to pay Syd to stay with Carter.

Michael insists on spending time with Kimberly after learning of her terminal illness. She reveals to Megan that she will crash her car during the next rainstorm. After it begins to rain, Megan forces Michael to drive her to Mulholland. She tells him the entire story of her relationship with Kimberly. Their car crashes into Kimberly's and flips into the air. Walter secretly pays a bill for Sydney after Taylor refuses to let Kyle bail her out. Sydney tries to tell Carter about Walter's behavior, but he interrupts to reveal that he wants a relationship. Amanda uses Craig's revelation to blackmail him. When Arthur learns that the secret is out, he confronts Craig and Amanda. He agrees to pay them five million dollars, but Craig tries to strangle his father. Arthur suffers a fatal attack. Jake and Alison get engaged. Peter threatens to ruin Dan's career unless he seeks counseling. Dan confronts Matt, who stops him from driving drunk. Dan apologizes and agrees to seek treatment.

Megan is furious to learn that Michael has slept with Kimberly. She forgives Michael, but then stakes out the beach house and nearly runs over Kimberly. Kimberly is astonished to learn that her tumor is in remission. Kyle gives Carter a job at the restaurant. Craig pays Nick to produce evidence of Taylor's affair with Peter. Taylor's liaison with Peter at the restaurant is interrupted when Kyle returns early from an out-of-town trip. Alison returns to work at D&D. A drunken Jake trashes the office. He leaves town, and decides to visit the home of his ex-girlfriend Colleen and their son, David. Colleen gives him advice about Alison, and he helps David deal with his anger over his adoptive father's frequent absences. Samantha is unnerved by a tender moment between Billy and Alison.

Amanda invita Craig a passare insieme un weekend, durante il quale chiarisce le proprie scelte di vita indipendente. Matt è ancora alle prese con la ribelle Chelsea, mentre Kimberly rientra in ospedale. Sydney rischia di perdere tutto per far fronte a una richiesta di risarcimento.