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.
When her brother decides to ditch for a couple weeks, Viola heads over to his elite boarding school, disguised as him, and proceeds to fall for one of his soccer teammates, and soon learns she's not the only one with romantic troubles.
Because of the notoriety she gained from the Miss United States pageant, Gracie Hart's life as an undercover F.B.I. Agent is over. In addition, Agent Eric Matthews broke off their relationship which she did not take well. Begrudgingly on the advice her boss, Director Harry McDonald, Gracie decides to become the F.B.I.'s media relations officer. Ten months later with the assistance of style coach Joel Meyers and a best selling book behind her about her experience, Gracie becomes a designer-clad media darling and the made-up face of the F.B.I. The new Gracie is the exact opposite of Agent Sam Fuller, a woman who, like Gracie before her pageant experience, has deep seated anger issues. The two do not get along, but that doesn't stop McDonald from assigning Sam to be Gracie's bodyguard. The two are sent to Las Vegas when Gracie's friend, reigning Miss United States Cheryl Frasier, and the long time Miss United States pageant host Stan Fields are kidnapped there. At the F.B.I.'s Las Vegas ...Written by
A Miss Congeniality (2000) poster can be seen in the background, at Las Vegas McCarran airport, during the scene where Gracie is supposed to be flying back to New York City. See more »
When Gracie is chasing Dolly Parton through the hotel (before going outside) her shirt rises and bit and you can see her microphone box. See more »
[FBI agents in a Jim & Dan's Fine Foods van on their way to the bank for a sting operation]
Hey Hart, can you give me Miss Arizona's number?
Why would I do that Clonsky?
Cause she needs a man in her life.
Yeah, where do you fit in?
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Outtakes are shown during the first part of the end credits. See more »