Kate Hudson and Matthew McConaughey star in this romantic comedy about two people determined to prove a point - opposing ones at that. Andie (Hudson) works on the advice column of a woman's magazine, but she yearns to be a serious journalist. When her friend, Michelle (Kathryn Hahn), complains of being dumped, and her editor (Bebe Neuwirth) is looking for someone to write an article on how to win and lose a man in ten days, Andie jumps at the chance; witnessed by two women from an advertising agency. Ben (McConaughey), meanwhile, works for the same advertising firm and is trying to win a place on a very big account with a diamond firm. Egged on by his two female colleagues, Ben tells his boss that he is the man for the job as he can make any woman fall for him within two weeks. The scene is set, Ben and Andie are set up to choose each other for their hidden agendas and the pair find that they have to work twice as hard to succeed...