Tom (Dempsey) and Hannah (Michelle Monaghan) have been best friends since college and it was the perfect set up for Tom: He had the smart, funny Hannah for companionship and got to sleep with as many hotties as he can get his hands on. Ten years later, they're still best friends with a side of sexual tension. It's not until Hannah leaves on a six-week business trip to Scotland that Tom realizes how much he depends on his weekly outings with Hannah and that he might actually have feelings for her. When she returns with hot Scottish fiance Colin (Kevin McKidd) in tow and asks Tom to be her "MOH" (Maid of Honor), Tom realizes he can't let the one person he truly loves get away. He accepts the assignment and sets out to become an "insider" in all things wedding in order to show Hannah she's marrying the wrong guy. Once in Scotland for the wedding, Tom does his best to derail the impending nuptials, failing dismally until the bachelorette party. Hannah has to smooch strangers in a pub, and Tom takes advantage of the opportunity. But when Hannah tries to talk to Tom about the kiss, she finds him in a compromising position with a randy bridesmaid (Busy Philipps). When he tries to explain, she sadly tells him that he waited too long -- she needs someone who will be there for her 100 percent.
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