On a college campus, a group of four girlfriends called Paige Prescott (Denise Richards), Dorothy Wheeler (Jessica Capshaw), Lily Voight (Jessica Cauffiel) and Kate Davies (Marley Shelton) ruthlessly humilate a nerdy kid, Adam Carr (David Boreanaz).
Ten years later, Adam has been physically transformed, shrugging off his baby looks and puppy fat to turn from an ugly duckling into a handsome, happening man. Now he prepares to wreak his revenge on the evil girls.
Through seduction and unpleasantness, he kills each of the women on Valentine's Day one year, after sending each of them a morbid valentine card.