How to Lose a Guy in 10 Days is a 2003 romantic comedy film directed by Donald Petrie, starring Kate Hudson and Matthew McConaughey. When his boss questions Ben's knowledge about romance, Ben bets he could make any woman fall in love with him if he wanted to. His boss accepts the bet and confirms that if he can make any woman fall in love with him before the upcoming company ball, in just 10 days, he will allow Ben to head the advertising for the new diamond company.