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Ben Stiller plays Reuben Feffer, a professional risk assessor who never takes chances in any aspect of his life. When his new bride Lisa (Debra Messing) leaves him for a European scuba instructor named Claude (Hank Azaria), he finally decides to a risk of his own. At a party, he meets free-spirited Polly Prince (Jennifer Aniston), whom he remembers from his seventh-grade Model U.N. Unlike the control-freak Reuben, she's spent her life living on the edge and they reluctantly begin a romance.