Michael must sell the beach house to pay off his debts. The voyeuristic real estate agent closes a deal within two days, then sleeps with Michael. Jane and Michael reminisce about their first date, but she tries to move on by going out with a dork from the office. Amanda plans to turn over day-to-day control of her agency to Ryan. A lazy lab technician's error convinces Kyle that he is sterile. Ryan and Megan's first date is a disaster, but they later admit their attraction and kiss. Lexi, Amanda and Eve organize a charity Christmas function. They visit a Christmas tree lot, where a former prison guard recognizes Eve. Lexi witnesses an argument between the two and suspects that Eve is hiding something about her past.

Kyle and Amanda are anxious to speed up the construction on their house, but learn that it will cost them. Amanda cannot afford to bring the apartment building up to code, so she decides to sell it. Kyle joins the construction crew for the house and offers to help Jane fix up the beach house. He helps her chase away a persistent but dorky neighbor. Dr. Shulman and the hospital's new corporate ownership try to stop Michael and Peter from treating uninsured patients. Jackie is assaulted by her boss. Dr. Shulman overhears Eve discussing her prison background with Jackie. She vows to use Eve's past to destroy Peter's reputation. Jackie holds Dr. Shulman at gunpoint, but Peter stops her from killing her. Jackie steals Dr. Shulman's car, then turns herself in, as she cannot handle life on the outside. Michael begins pursuing Megan. Lexi tries to goad Megan into popping the question to Ryan, but he beats her to the punch. He suddenly leaves town. Ryan goes to a boarding house in Poughkeepsie