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.
Anna Foster has never had an ordinary life. At eighteen years old, she is the most protected girl in America; she is the First Daughter. Frustrated with her overprotective father, the ... See full summary »
At a Wisconsin university, local farmer's daughter Paige Morgan is intrigued by odd Danish exchange student Edvard 'Eddie', who is ignorant of many aspects of daily life, such as all ... See full summary »
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
Keni Thomas, lead singer of the band Cornbread that plays in the fair scene is a real-life survivor of Task Force Ranger and is portrayed in the film Black Hawk Down (2001) (the trooper with the inhaler). See more »
Melanie jokingly asks if the Piggly Wiggly ran out of soap. There is no Piggly Wiggly within 100 miles of where the story is set. See more »
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 »