Eric agrees to cease his takeover of the restaurant and jazz club if Amanda sleeps with him. Megan quits her job after learning of the offer. She shares the news with Taylor, who tries to blackmail Amanda into going through with it. Someone torments Michael by planting items that belonged to Kimberly around his home and office. Peter and Lexi tell him about Brett's relationship with Kimberly. Michael confronts Brett, who is arrested for punching him. Michael's stalker fires shots at him at the beach house. Craig gives Jennifer a car as a reward for her success in promoting the cauterizer at a medical supplies convention. Lexi hides a pill addiction from Peter. Sam demands an expensive wedding dress.

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.