Cast: Matthew McConaughey, Bebe Neuwirth, Adam Goldberg, Kate Hudson, Michael Michele, Marvin Hamlisch, Marv Albert, Craig Castaldo, John DiResta, William Duell and others
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. 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.
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