Reuben Feffer (Ben Stiller) makes a living as a risk assesor for an insurance company and hates taking risks in his own life. His excessive compulsiveness over germs, upsets his stomach and does not allow him time to relax.
Lisa (Debra Messing), is his new bride and on their honeymoon he catches her bedding down with the French speaking scuba instructor Claude (Hank Azaria). Returning home alone, his best friend Sandy Lyle (Philip Seymour Hoffman) and his obnoxious boss Stan Indursky (Alec Baldwin), try to console him. He knows he must get back into life but doesn't know how. And then along came Polly.
Polly Prince (Jennifer Aniston), is bartending a party that Ruben attends and she recognizes him from back in 7th grade. She's a free spirited fun risk taking girl, who owns ferets for pets. After their chance meet, Reuben takes his first major risk on inviting her out. One spicy meal later, Reuben finds himself trying to play it cool while his stomach erupts but he's determined to do what ever he needs to attrack Polly's affection. From salsa dancing to extreme sports, Reuben lets it all hang out and finds that living in the moment is the best risk he's ever taken.
Director: John Hamburg
Writer: John Hamburg
Producers: Danny DeVito, Stacey Sher, Michael Shamberg