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A friendly insurance actuary who likes living life by the book (Stiller) makes a living analyzing risk for insurance purposes, but finds his wife (Messing) cheating on him on their honeymoon with a French scuba instructor (Azaria). Distraught, the estranged actuary gets involved in a risky romance with Polly Prince, an extroverted former classmate (Aniston), only to later find his wife..
...desperate to rekindle their marriage. Reuben doesn't want to get back together with his wife and wishes to stay with Polly. He then enters her and his wife into an insurance program which decides if a person is risky to be insured. In the meantime, Reuben is trying to insure Lew (Brown), a businessman who takes high-risks.
Along came Polly
