Actuary Reuben Feffer (Ben Stiller) is so aware of the risks inherent in all situations that he is unable to risk anything. His bride, Lisa Kramer (Debra Messing), seems perfect but cheats on him during their honeymoon. Back home in New York City, his best friend, former child star Sandy (Philip Seymour Hoffman), urges him to attend a party. There he meets an ex-classmate, Polly Prince (Jennifer Aniston), whose spirited ways spark his adoration but confound his neuroses.