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When three popular girls from different cliques discover they've all been dating the school stud, they band together to seek revenge. Despite the jerk's charm and ever-growing popularity, the girls cleverly scheme with the help of the inconspicuous new girl in town, to soil his reputation and break his heart.
In this comedy, Lindsay Lohan plays Ashley, a young professional just out of college. She also happens to be the luckiest woman in the world, who has lived a super-charmed life and has always taken her good luck for granted. When she kisses a handsome stranger (played by Chris Pine) at a costume party, Ashley accidentally swaps her good fortune for his horribly bad luck, and her charmed life turns into a living hell.