How to Lose a Guy in 10 Days

(2003)Directed by Donald Petrie116 min · PG-13Comedy, Romance
One of them is lying. So is the other.

Andie Anderson (Kate Hudson), a magazine writer, bets she can sabotage any relationship in ten days by being deliberately impossible. Benjamin Barry (Matthew McConaughey), an advertising executive, has just wagered that he can keep a woman devoted to him for that exact span of time. They meet by chance, and both see a chance to win, so they begin dating while secretly working to destroy what they have built.

Kate Hudsonas Andie Anderson
Matthew McConaugheyas Benjamin Barry
Kathryn Hahnas Michelle Rubin
Annie Parisseas Jeannie Ashcroft
Thomas Lennonas Thayer
Michael Micheleas Judy Spears
Shalom Harlowas Judy Green
Robert Kleinas Phillip Warren
Bebe Neuwirthas Lana Jong
Samantha Quanas Lori
Justin Peroffas Mike
Celia Westonas Glenda
Archie MacGregoras Uncle Arnold
John DiRestaas Joey Sr.
Scott Benesas Joey Jr.
Zachary Benesas Joey Jr.
William Hillas DeLauer Security
Georgia Craigas Receptionist Candi
Liliane Montevecchias Mrs. DeLauer
James Mainprizeas Mr. DeLauer
Tony Longoas Sensitive Moviegoer