How to Lose a Guy in 10 Days - Andie Anderson (Kate Hudson) decides to spice up her How-To column in Composure Magazine by venturing out into the Manhattan singles market to see if she can make a guy fall for her, and then get him to dump her within 10 days. Simultaneously, advertising executive Benjamin Barry (Matthew McConaughey) makes a bet with his boss that he can meet a woman and have her fall in love with him within 10 days.