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.