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.
Director: John Hamburg
Producer: Danny DeVito, Michael Shamberg, Stacey Sher, Jane Bartelme and Dan Levine
Cast: Ben Stiller, Jennifer Aniston, Philip Hoffman, Debra Messing, Hank Azaria, Bryan Brown, Alec Baldwin, Jsu Garcia, Michele Lee and Bob Dishy