Tom Bailey (Patrick Dempsey) is in love with his best friend Claire (Michelle Monaghan). But Tom has a fear of commitment and refuses to admit the obvious – he should propose to Claire before she finds a less procrastinating suitor. When Colin, a rich Scotsman sweeps Claire off her feet and asks for her hand in marriage, Tom must witness her unquestioned happiness up close and personal – because she’s chosen him to be her “Maid Of Honor.”