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Patrick "McDreamy" Dempsey leads this big budget romantic comedy, making optimal use of his many swoon; inducing charms. Dempsey is Tom, a wealthy womanizer living the high life in New York City. He happily hops from bed to bed, living by a firm set of rules that keeps him from becoming romantically entangled with anyone. The only woman he makes time for is his dear college friend, Hannah (Michelle Monaghan), whom he sees weekly, and whom he adores. When Hannah suddenly takes off for Scotland on.