Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days. Kate Hudson twinkles as the heroine of How to Lose a Guy in 10 Days, a magazine writer assigned to date a guy, make all the mistakes girls make that drive guys away (being clingy, talking in baby-talk, etc.), and record the process like a sociological experiment.

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. However, the guy she picks--rangy Matthew McConaughey--is an advertising executive who's just bet that he can make a woman fall in love with him in ten days; if he succeeds, he'll win a huge account that will make his career.

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