An obsessively cautious man, whose wife left him on their honeymoon, crosses paths with a wildly spontaneous former classmate who throws his well-oiled routine into disarray. Yet in spite of their different outlooks on life, he starts to fall for her. Romantic comedy, starring Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman, Debra Messing, Hank Azaria and Alec Baldwin.

Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.