Career-driven single woman Kate Mosley (Jennifer Aniston) is trying to get ahead in her advertising job and discovers that her boss is more inclined to promote married people. When her friend Darcy (Illeana Douglas) suggests that she use a photo of an acquaintance as proof of a fake fiancé, the deception seems to work, and Kate gets promoted. However, when her boss wants to meet Kate's husband-to-be, she has to track down the guy, Nick (Jay Mohr), and talk him into playing along with the ruse.