Jane learns that her grandmother has died and goes to her home town in Chicago for the funeral to receive $100,000 in inheritance to start her own clothing business. But when Michael finds out about the money, he and Sydney go after it. Jo meets a model named Gregory, but he leaves her when he finds out that she's pregnant. Meanwhile, Alison and Billy travel to her home town in Wisconsin to visit her parents and to plan her father's surprise 50th birthday party, where Billy discovers that she has not told her parents about their engagement.