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Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made. She catches John Tucker (Jesse Metcalfe) dating three different girls at once: Carrie - the smart girl, Heather - the cheerleader, and Beth - the activist slut; none of them are aware that they are not the only girl in John's heart.