Swinging single Tom (Dempsey) brags to his buddies that he lives a perfect life: he bags a new babe almost every night and still has the companionship of his lovely long-time best friend Hannah (Monaghan) for balance. But when Hannah returns from a Scotland vacation with the ultimate souvenir--a fiance--Tom quickly realizes he's missed his chance at true love. He accepts her offer to be the "maid" of honor (thus the ultra-clever title), hoping to sabotage the wedding from the inside. Little more than a bland gender-reversed version of "My Best Friend's Wedding" with paper-thin characters that bomb the chemistry test.