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The One-Line Summary: A guy who knows a thing or two about risk assessment, insurance expert and rigidly structured Reuben Feffer (Ben Stiller) catches his wife Lisa (Debra Messing) cheating on their honeymoon and heads home to gather his senses, not at all expecting to run into Polly Prince (Jennifer Aniston), a school classmate who lives for the moment and challenges Reuben to take a few more gambles in life.
The Two-Line Blurb: This innocuous rom-com is strictly by the numbers but is raised by some solid and often funny performances that get a few laughs, especially from Stiller who, at this stage in his carer, found a string of comedies that fit his manic, awkward-man style perfectly. But it is the late Philip Seymour Hoffman who hands down steal every scene he is in and displays a brilliant capacity for comedy that is so good one wonders if the film might have been better if it was about him instead.
The Three-Line Set-up: As Reuben grows closer to Polly, she constantly pushes him to try more and more adventurous things, which predictably ends in disaster, even if it is loosening him up a bit. From ethic restaurants to salsa dancing, Reuben is broadening his horizons but it’s taking its toll. When his cheating wife comes back looking for a second chance, he has to decide between the care-free Polly and the stable Lisa.
The Four-Line Moment: While assessing the risks of insuring Leland Van Lew (Bryan Brown), a potential client, Reuben invites Polly to join them on a sail boat, piloted by Van Lew. On the boat, she discovers the computer program that Reuben is using to weigh the ups and downs of the two women and it infuriates her, especially once he confesses that he wants Polly to move in with him. As they argue and Reuben tries to salvage their relationship, a storm rocks the boat, knocking the two characters about the cabin. The juxtaposition of the two lovers fighting and the metaphorical use of the ship in rocky waters is a wonderful little moment in a often bland but occasionally rewarding comedy.
The Five-Word Review: Watch this for Hoffman only.