Patrick Dempsey (Grey's Anatomy) leads this big-budget romantic comedy, making optimal use of his many swoon-inducing charms.
Dempsey is Tom, a wealthy womaniser 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 a job assignment, Tom misses her terribly, and has a dramatic realisation about their relationship. He makes a plan to tell her about it as soon as she gets back but of course she returns with a handsome Scottish fiance (Kevin McKidd) in tow. To make matters worse, she informs Tom that she must make wedding plans rather quickly and would he please, please, please be her Maid of Honour?
In typical rom-com fashion, the tale quickly escalates into over the top, barely believable plot twists, forcing the viewer to turn a blind eye to any holes in the story and instead focus on the pretty clothes and Dempsey's dimples. It shifts into full-on fantasy mode, with rugged lads on horseback, Scottish castles and gargantuan New York apartments that only Bill Gates himself could afford.