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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.
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.