Henry's girlfriend breaks up with him right after she convinces him to move to Chicago. With nowhere to turn, he responds to an ad placed in the paper by Larry Cone for a roommate, and he helps Henry begin his life anew.
Henry finds an old Mix CD stuffed in the back of Larry's closet. The questions he rises about the CD unravels an old relationship Larry had years ago. Amanda dates a gynecologist, who, after an appointment with her, suspiciously cancels their date that night.
Henry puts his engagement ring for sale on eBay. Then Amanda wants to borrow it to hurt an ex by pretending to be in a relationship. Heather returns, wanting to give Henry another try. Tina kicks Brad out because he hasn't given her a ring.
Amanda meets her college friend Lucy, who points out that Amanda's the only one in their former clique still single. So Lucy pushes Amanda into online dating. Henry asks a coffee shop girl out despite the others' claim that she's a lunatic.