Benjamin Barry is an advertising executive competing with two female co-workers for a major campaign for a diamond merchant. He cuts a deal with his competitors that the account is his if he can make a woman of their choice fall in love with him in 10 days. In comes Andie Anderson who, in turn, is writing a story on how to lose a guy in 10 days as a bet with her boss to be allowed to write more substantial stories. With a hidden agenda in each camp, will either party be able to complete their mission?