Oscar® nominee* Kate Hudson (Almost Famous) and Matthew McConaughey (A Time to Kill) give the battle of the sexes an outrageously unexpected twist in the runaway comedy hit the Daily News applauds as "Hilarious!" As the "How to..." columnist for trendy Composure Magazine, Andie Anderson (Hudson) agrees to write a first-hand account about what it takes to drive a man out of your life...in exactly 10 days. At the same time, eligible ad agency bachelor Benjamin Barry (McConaughey) accepts a high-stakes bet that he can lure any woman into falling head-over-heels in love with him...also in 10 days. The resulting romantic head-on collision ignites a series of deliriously comic deceptions that prove when it comes to true love...your heart cannot tell a lie.
*Academy Award® nomination, Best Supporting Actress, Almost Famous, 1999
| Kate Hudson | Andie |
| Matthew McConaughey | Ben |
| Kathryn Hahn | Michelle |
| Annie Parisse | Jeannie |
| Adam Goldberg | Tony |
| Thomas Lennon | Thayer |
| Michael Michele | Spears |
| Shalom Harlow | Green |
| Robert Klein | Phillip Warren |
| Bebe Neuwirth | Lana Jong |
| Samantha Quan | Lori |
| Justin Peroff | Mike |
| Celia Weston | Glenda |
| James Murtaugh | Jack |
| Archie MacGregor | Uncle Arnold |
| John DiResta | Joey Sr. |
| Scott Benes | |
| Zachary Benes | |
| Rebecca Harris | Dora |
| Liliane Montevecchi | Mrs. DeLauer |
| James Mainprize | Mr. DeLauer |
| William Hill | DeLauer Security |
| Georgia Craig | Receptionist Candi |
| Tony Longo | Sensitive Moviegoer |
| Warner Wolf | Himself |
| Doug Murray | Mark Sawyer |
| Natalie Brown | Mrs. Sawyer |
| Andrew Moodie | Poker Pal Ronald |
| David Macniven | Poker Pal Francis |
| Jeff Gruich | Poker Pal Joe |
| William Duell | Old Concession Worker |
| Ross Gallo | Young Concession Worker |
| Gina Sorell | Vegetarian Waitress |
| Diego Fuentes | Kitchen Worker |
| Ingrid Hart | Mullen's Hostess |
| Al Bernstein | Party Waiter |
| Marvin Hamlisch | Himself |
| Collin Barrett | |
| Bruce Farquhar | |
| Rod MacDonald | |
| Bob Reeves | |
| Gery Soles | |
| Jim Paris | |
| Frank Penny | |
| Marv Albert | The Voice of the NY Knicks |
| Randy Kerdoon | Court Announcer |
| Harry | |
| Izzy | |
| Richard Vane | Executive Producer |
| John Bailey | Director of Photography |
| Debra Neil-Fisher | Film Editor |
| David Newman | Composer |
| Tod A. Maitland | production sound mixer |
| Mark P. Stoeckinger | Supervising Sound Editor |
| Frank Smathers | Supervising Sound Editor |
| Andy Nelson | Sound Re-Recording Mixer |
| Anna Behlmer | Sound Re-Recording Mixer |
| Douglas Ganton | production sound mixer |
| Karen Patch | Costume Designer |
| Thérèse DePrez | Production Designer |
| James C. Feng | Art Director |
| J. C. Brotherhood | Visual Effects |
| Cheryl Kilbourne-Kimpton | Costume Designer |
| Amelia Andrews | Costume Designer |
| Bernadette Mazur | Make-Up Artist |
| Ronnie Specter | Make-Up Artist |
| John T. Van Vliet | Visual Effects |
| Raymond McIntyre, Jr. | Visual Effects |
| Brandt Gordon | Art Director |
| Mia Sturup | Costume Designer |
| Linda Dowds | Make-Up Artist |
