Benjamin Barry (McConaughey) 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 (Hudson) 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.
Kathryn Hahn....Michelle Rubin
Annie Parisse....Jeannie Ashcroft
Thomas Lennon (III)....Thayer
Robert Klein (I)....Phillip Warren
Bebe Neuwirth....Lana Jong
Archie MacGregor....Uncle Arnold
Filmography links and data courtesy of The Internet Movie Database.