Life is great for Tom (Patrick Dempsey). He's good-looking, rich, and has a best friend in Hannah (Michelle Monaghan) who helps round his life. Life is going great until Hannah gets an assignment to visit a museum in Scotland. From the moment she's gone, Tom notices a gap in his life. His bevy of beauties are shallow and uninteresting and hesuddenly feels lost. He tries several times to call Hannah while she is overseas, but the time difference and a series of events prevent it. Tom is quickly convinced that his life will only have meaning if Hannah is a part of it. He vows to tell her how he feels when she comes back to New York. When she does return, she brings back a bit of Scotland, in the form of a fiancee - Colin; a wealthy, handsome duke who rescued her in a thunderstorm in Scotland.
She asks him to be her maid of honor, as she had always assumed she would be his best man if he had gotten married. He is reluctant to take the job, but is convinced to do so by his buddies so that he can undermine the wedding. Along the way, he has to deal with a jealous bridemaid, Colin, and a host of other obstacles.
Basically, this movie is very close to My Best Friend's Wedding (starring Cameron Diaz and Julia Roberts) with a simple gender reversal. The biggest difference is where Julia Roberts comes across as a bitch and totally unsympathetic, Tom comes across as genuine and earnest in his efforts to woo his one true love. This movie also gets the romantic comedy formula correct and adds just the right touches of humour and romance to the mix to make it work. Little touches like how Tom got rich and Colin's unassuming character add real charm to the movie.
I have to admit I wasn't really expecting to enjoy this film, but it was a pleasant surprise.