I have seen this movie a hundred times, and I still cry my eyes out when she's at his funeral..."where are his glasses? get his glasses, he can't see without his glasses!!!" Rips my heart apart every time.
"How to Lose A Guy in 10 days?" (2003) -- Kate Hudson, Matthew Mcconaughey -- 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.