Rueben Feffer (Ben Stiller) assesses insurance risks for a living. He leads a simple and controlled life with as little risks to his health and safety as possible. He thinks he has found the love of his life in Lisa (Debra Messing), but on their honeymoon Rueben finds Lisa in bed with their scuba diving instructor. Rueben is not the type to lash out, and he simply accepts the fact that his wife is cheating and leaves.

Soon he meets Polly Prince (Jennifer Aniston), a quirky, adventurous woman who is unafraid to live her life. She breaks rules, plays extreme sports and eats spicy foods; everything Rueben doesn’t. Rueben is instantly infatuated with Polly and is left with a dilemma; whether he should try his luck even though it means changing his boring, overanxious lifestyle.