On Valentine’s Day, unpopular middle-school student Jeremy Melton is ruthlessly humiliated by a group of five girlfriends (Richards, Capshaw, Heigl, Cauffiel, Shelton), playing a nasty practical joke. When the prank goes horribly wrong, Jeremy is expelled and spends ten years in juvenile hall and reform school. During that time, he remakes himself, but his hatred for his tormentors continues to burn. When he is released, Jeremy has transformed himself into a handsome, charismatic man bent on revenge.

Thirteen years after they ruined Jeremy's life, the five friends begin to receive morbid and threatening Valentine's cards. Could it be Jeremy? The girls soon realise that the middle school laughing stock has not forgotten what they did to him.

Katherine has a key cameo role as Shelley Fisher appearing for the first 15 minutes of the film.