Sydney resents Jane's new relationship with her mother. Sherry lies about the identity of Jane's biological father, but later reveals that he was a producer with whom she had slept to win a part. Amanda and Craig take a business trip to Palm Springs. When Peter arrives to surprise Amanda, he finds her having dinner with Craig and wearing a pearl necklace. Peter refuses to listen to her explanation, and trashes the restaurant. Amanda throws him out of the apartment. Taylor decides to donate one of Samantha's paintings to a charity auction. Sam (who hasn't received any money from the sales) tries to buy it back, but Sydney bids on the painting to drive up the price and make Kyle look generous. Sydney is in a bind when she accidentally buys the painting, and hopes that the man who bid against her will take it off her hands. He is actually an employee of computer genius Carter Gallavan, who buys the painting and takes a liking to Syd. Billy retrieves the painting that Sam gave to Craig. Bi

Michael tries to reunite Peter and Amanda in the hopes that Peter will again make a contribution at the office. Kyle tries to play matchmaker at his birthday party, but Amanda isn't ready to talk to Peter. Peter regains his confidence when he witnesses an accident and saves the driver with an emergency tracheotomy. Carter gives Sydney a beautiful sports car, but is too busy to spend time with her. Samantha sleeps with Billy after he secretly buys a bunch of her paintings to try to help her make it to a family reunion. Michael is reluctant to sign the divorce papers. Kimberly convinces Megan to take Michael to Las Vegas in the hopes that he will marry her. Sydney confronts Jane when her sister rejects the Andrews family to spend all her time with Sherry. Sherry's boyfriend Ed tells Jane that her mother is an alcoholic, and has begun drinking again because of her guilt about giving up Jane. Dan becomes physically abusive toward Matt.

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.