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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Adam Goldberg , Al Bernstein , Andrew Moodie , Annie Parisse , Bebe Neuwirth , Bob Reeves , Celia Weston , Craig Castaldo , David C Roehm Sr , David Macniven , Diego Fuentes , Doug Murray , Frank Penny , Georgia Craig , Gina Sorell , Ingrid Hart , James Mainprize , James Murtaugh , John DiResta , Kate Hudson , Kathryn Hahn , Liliane Montevecchi , Marv Albert , Marvin Hamlisch