 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.