A man who's afraid of risk (Stiller), but makes a living analyzing risk ends up getting involved in a risky romance (Aniston), cheating on his new wife (Messing), which turns his stable life upside-down. Sense a theme? (Hoffman plays Stiller's best friend; Baldwin plays his boss; Brown plays a sky-diving, bungee-jumping "adrenaline junkie" seeking a life insurance policy; Silpa plays the director of a play who comes into conflict with Hoffman's character; Azaria plays a French scuba instructor who flirts with Messing's character while she and Stiller's character are on their honeymoon; Michele Lee plays Stiller's mother and Dishy plays her husband.)
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