A handsome and successful bachelor is taken aback when his dream girl asks him to be the "maid" of honor in her upcoming wedding in this romantic comedy starring Patrick Dempsey and Michelle Monaghan. Tom (Dempsey) and Hannah (Monaghan) have been best friends for years. Though all the hard times, Hannah has been the one constant in Tom's life, and the one person he knows he can always rely on. When Hannah leaves for a six-week business trip in Scotland, Tom is surprised to realize how truly lonely he is without her. Life just isn't the same without Hannah around, so the moment she returns, Tom resolves to ask for her hand in marriage. But apparently Hannah's trip wasn't all business, because upon returning home Hannah announces that she has gotten engaged to a dashing Scotsman and will soon be starting a new life overseas. She's convinced that Tom will be thrilled for her, and wants him to play a crucial role in the wedding. His spirits crushed but his love for Hannah stronger than ever before, Tom reluctantly agrees to be the "maid" of honor so that he can prove his love in no uncertain terms and convince her to call off the wedding before true happiness slips through his fingers.
~ Jason Buchanan, All Movie Guide