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.
Single-girl anxiety causes Kat Ellis (Messing) to hire a male escort (Mulroney) to pose as her boyfriend at her sister's wedding. Her plan, an attempt to dupe her ex-fiancé, who dumped her a couple years prior, proves to be her undoing.
Mary Fiore is San Francisco's most successful supplier of romance and glamor. She knows all the tricks. She knows all the rules. But then she breaks the most important rule of all: she falls in love with the groom.
Melanie Carmichael, an up and rising fashion designer in New York, has gotten almost everything she wished for since she was little. She has a great career and the JFK-like fiancée of New York City. But when he proposes to her, she doesn't forget about her family back down South. More importantly, her husband back there, who refuses to divorce her ever since she sent divorce papers seven years ago. To set matters straight, she decides to go to the south quick and make him sign the papers. When things don't turn out the way she planned them, she realizes that what she had before in the south was far more perfect than the life she had in New York City. Written by
An entire character (along with a subplot about her) was deleted from the film, when test audiences consistently misunderstood her relationship with Andrew. Erin Vanderbilt (played by Katharine Towne) survives in the finished movie only in a newspaper wedding announcement shown to Melanie during the closing credits. See more »
After Melanie visits the Carmichael estate, she is walking down the street in town with the sleeves of her dress pulled down past her shoulders, not up on her shoulders as they were in the previous shots. See more »
You know for someone whose been holding onto something for so long, you're pretty quick to let it go.
I can't control her, any more than I can control the weather.
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During the end credits some photos are shown with the cast. In a sequence of them Melanie's parents are "scared" by a punk with a pierced tongue, Mel's co-worker from the beginning of the movie, who comments on her accent when she dreams. See more »
Reese Witherspoon sweet performance makes this work
Reese Witherspoon terrific heartfelt performance makes this movie work. I originally had my doubts about seeing this one but I bought the DVD and I highly enjoyed the movie. Reese Witherspoon has good chemistry with both Patrick Dempsey and Josh Lucas. The film although predictable is full of funny moments and a lot of heart.
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