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?

Well, Polly probably didn’t have tattoos in junior high. Or have a penchant for spicy food, steamy salsa dancing or collecting tokens from boyfriends past…like the near-blind ferret she picked up in Italy. And Reuben—his propensity to plan everything in his life may not have been as all-encompassing in middle school, nor his compulsion with living in the middle of the road as pronounced.

But even in the middle of the road, Reuben finds that there are bound to be bumps—like indigestible food, scary children’s stories, sight-impaired house pets. Life is risky, and so is love…and with Polly along for the ride, could one expect (or enjoy) anything less?