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.

Director: Donald Petrie

Cast: Kate Hudson, Matthew McConaughey, Kathryn Hahn, Annie Parisse, Adam Goldberg, Thomas Lennon, Michael Michele, Shalom Harlow, Robert Klein, Bebe Neuwirth, Samantha Quan, Justin Peroff, Celia Weston, James Murtaugh, Archie MacGregor