Romantic comedy starring Patrick Dempsey. When serial womaniser Tom's (Dempsey) long-time best friend, Hannah (Michelle Monaghan), becomes engaged to Colin (Kevin McKidd), Tom comes to the realisation that Hannah is in fact the woman he wants to be with. Tom agrees to become Hannah's maid of honour, seeing it as an opportunity to get closer to the bride-to-be and woo her before it's too late. As Hannah begins to realise that Tom may be marriage material after all, she will have to decide between marrying her best friend or the man who asked her first.