Along Came Polly (HBO)
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Risk management goes out the window for an insurance analyst who starts dating a bohemian girl after his marriage goes south. Ben Stiller stars as Reuben Feffer, a risk-assessor who comes to the realization that he needs to take some chances on love. Enter Polly (Jennifer Aniston), an indecisive waitress whose spicy style is just the tonic to break Reuben out of his shell.
Starring: Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman, Debra Messing, Hank Azaria, Bryan Brown, Alec Baldwin