Romantic comedy starring Jennifer Aniston and Ben Stiller. Reuben (Stiller) is a risk assessor for an insurance company, and hates taking risks of any kind. But when his new bride runs off with the diving instructor on their honeymoon, he begins to wonder if his risk assessment is so accurate after all. On his return from his disastrous honeymoon, he runs into the beautiful, free-spirited Polly (Aniston), an old acquaintance from junior high, at a party. But is he ready to put his feelings on the line, let himself go and have some fun with her?
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