A high-stakes poker game pits Simon Elder against Tripp; if Nick convinces Tripp to bet his most prized property, Elder will give Nick dirt on his father's death; Karen must finalize her divorce from irresistible Sebastian Fleet (guest star Eddie Cibrian).
Charlie and Mac's old high school gym teacher is accused of molesting their former peers; Dee and Dennis suspect that Charlie is also a victim.
Matt asks someone to be his "plus one" at Wilhelmina's fundraiser; Daniel hires Natalie to be his assistant, making Betty feel obsolete; Amanda keeps a secret from Betty; Daniel discovers that his mother has a history with Cal Hartley.
Jess struggles to keep the loft’s Secret Santa gift exchange afloat. When Winston believes his online gift order for Cece won’t be delivered in time he and Schmidt must endure going to an actual store to find a replacement gift. Meanwhile Reagan surprises Nick who helps makes Jess’ Christmas one to remember.
Molly (guest star Heather Graham) announces to everyone that she's moving away for a new job opportunity, which stirs the waters of the triangle between herself, J.D. (Zach Braff) and Elliot (Sarah Chalke). When J.D. and Molly end up making-out at her going-away party, Elliot plays games with J.D. when he asks for her blessing for him to sleep with Molly before she leaves town. Meanwhile, Dr. Cox (John C. McGinley) has to fulfill community service hours and gets stuck riding around with a neurotic ambulance driver (guest star Molly Shannon) who drives him insane. Donald Faison, Judy Reyes and Ken Jenkins also star.
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