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How to Lose a Guy in 10 Days (2003) - Kate Hudson, Matthew McConoughey, Adam Goldberg, Kathryn Hahn & Bebe Neuwirth - Benjamin Barry 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 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.
Evelyn Couch: Hey! I was waiting for that spot! Girl #1: Face it, lady, we're younger and faster! [Evelyn rear-ends the other car six times] Girl #1: What are you *doing*? Girl #2: Are you *crazy*? Evelyn Couch: Face it, girls, I'm older and I have more insurance.
I watched this a thousand times when I was little!