Benjamin Barry (Matthew 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 (Kate 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.