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For Tom (Patrick Dempsey), life is good: he’s sexy, successful, has great luck with the ladies... and knows he can always rely on Hannah (Michelle Monaghan), his down-to-earth, charming best friend and the one constant in his life.  It’s the perfect setup until Hannah goes overseas to Scotland on a six-week business trip... and Tom is stunned to realize how empty his life is without her.  He resolves that when she gets back, he’ll ask Hannah to marry him - but is floored when he finds that she has become engaged to a handsome and wealthy Scotsman and plans to move overseas.  When Hannah asks Tom - the one person she feels closest to - to be her “maid” of honor, he reluctantly agrees to fill the role... but only so he can attempt to woo Hannah and stop the wedding before it’s too late.