Michael attends a college reunion in Chicago, where he runs into Jane. They seem to instantly renew their connection, but Jane tells him that she is to marry in a few days. Michael later learns that this is not true, and the two reminisce about the good times in their relationship. After a night of passion, Jane follows Michael back to Los Angeles in the hopes of rekindling their romance. Megan and Brett struggle to find time together in the face of Lexi's interference. Peter turns to a shady former patient for assistance after his attempts to woo Amanda prove an unqualified failure. Billy and Samantha vie for an Italian client's in-house advertising position. Jennifer mistakenly believes that Billy plans to leave the country without her. Billy and Jen get engaged--in front of Sam. Samantha launches a plan after overhearing Billy and Amanda discuss Alison's renewed alcohol problem and failed professional life.

Michael has Taylor shipped away in an ambulance, but she and Jane later discover each other. Jane is furious to learn of the pregnancy, and rents an apartment at the complex. Amanda recruits her for a job at AWA. Jane reconciles with Michael, and agrees to help care for Taylor. Taylor decides that she isn't fit to be a mother and asks Jane and Michael to adopt her baby. Peter is uneasy about the plot he arranged with Mr. Beck. He is unable to call it off, and Amanda is kidnapped. Samantha convinces Jeff to send Billy a fax in which ""Alison"" expresses her love for him. Billy claims that he only wishes to help Alison, but Jennifer fears that he still holds feelings for her. Lexi continues to taunt Megan about her marriage, and goads Brett into sleeping with her.

Beck's men hold Amanda hostage in a desolate cabin. She escapes, but is quickly re-captured. Kyle is forced to turn to Peter for help when the kidnappers demand a million-dollar ransom. Peter volunteers to leave the money at the drop site after the kidnappers refuse to let Kyle do it himself. Peter arrives at the cabin to find that Amanda is gone. She has escaped again, with one of Beck's men in hot pursuit. Jen is distraught when Billy insists that he will visit Alison in Atlanta. A disgusted Jeff breaks up with Sam. He accepts a job as a sports radio talk show host in Tampa. Sam tells Jennifer that she sent the fax, but Jen keeps the news from Billy in order to test their relationship. Michael tells Billy the truth, and he breaks up with Jennifer. Lexi orders Brett to stop seeing Megan. She also angers him by purchasing an expensive sailboat. Brett begs Megan to leave the country with him, but she learns that he slept with Lexi. Brett suddenly pretends that he is in love with Lexi, t

Matt dies in a car accident while on his way to dinner at Kyle's club. His mother gives Amanda a diary in which he recorded secrets about his friends and neighbors. Jane is amused to learn that Michael worked as a stripper during college; but their new engagement is threatened after she reveals that she slept with an old friend, Alex Bastian, the night before their wedding. Amanda learns from the diary that Kyle has a brother named Ryan. They quarreled after Kyle accused Ryan of making a pass at Taylor. Amanda convinces Kyle to bury the hatchet. Amanda removes an incriminating page from the diary. Beck returns the ransom money to Peter. Amanda tells Peter that the diary revealed that he performed heart surgery on Beck while he was unlicensed. Peter believes that the missing page relates to Amanda's feelings for him, and snoops in her apartment. Amanda mistakes him for a burglar and shoots him. Lexi decides to branch out into advertising. A distraught Megan throws herself at Michael, th