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How to Lose a Guy in 10 Days: Directed by Donald Petrie. With Kate Hudson, Matthew McConaughey, Kathryn Hahn, Annie Parisse. 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.. True rom-com stans always have 2003's How to Lose a Guy in 10 Days on the movie rotation.. The latest fashion news, beauty coverage, celebrity style, fashion week updates, culture reviews.