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Reuben Feffer (Ben Stiller) believes that if you plan ahead and play it safe, you can have a pretty good life. When his wife of a few days (Debra Messing) dumps him on his honeymoon for their scuba-diving instructor (Hank Azaria), Reuben vows to keep things under an even tighter lid. But along comes Polly (Jennifer Aniston), a bright, buoyant and breathtakingly irreverent childhood friend who teaches him to live life on the edge.