Reuben Feffer (BEN STILLER) has made a fine life—and a good career—out of playing it safe. The star risk assessor for a leading insurance firm, Reuben is an expert on minimizing danger—nothing ventured, nothing lost.
Polly Prince (JENNIFER ANISTON) plays her life like a game of chance, taking joy from the serendipity that a rolling stone existence brings her. There’s always another opportunity—a new job, yet another apartment in another city—should this one not work out. No biggie…next.
So when a chance meeting puts Reuben and Polly at the same party, the recently (and extremely) jilted Reuben decides that for once, chance may just be on his side. Dating Polly might be the answer to getting his life back on track—she’s attractive, fresh, funny—and after all, the two knew each other in seventh grade, when they were both delegates in the Model U.N. together. Just how much can a person change?