David (Jerry O'Connell) and his girlfriend, Sarah (Bridgette Wilson), have been together for five years, and now she's forcing him to make a decision--while she's away for two months, he has to either decide to marry her or face losing her. To help him make his decision, David calls on his lady killing best pals (Ryan Reynolds and Bill Bellamy) to hit the town with him and check out the L.A. singles scene to see if he can find a better alternative to what he's already got! While out on the town, David meets a seductive mystery woman--at the same time that Sarah's dashing boss puts the moves on her in New York. Will these two stick together or head for greener pastures