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Ashley (Lindsay Lohan)
has always been the sort of girl fortune smiles upon, she's pretty, she has a
great job, she has good friends, guys fall over themselves to ask her out, and
she never has trouble getting a cab. Jake (Chris Pine), on the other hand, is
not nearly so lucky, he's clumsy and accident prone, things never seem to go his
way, and he's just lost his job. However, these two opposites meet one night at
a ritzy masquerade ball, and Ashley and Jake exchange an impulsive kiss as two
shooting stars cross in the sky. Suddenly, they both find their luck taking a
one hundred and eighty degree turn; Jake is befriended by a wealthy musician and
suddenly finds himself successful and flush with cash, while Ashley loses her
job and her apartment after a major misunderstanding with the police. While
Jake's luck with women has also taken a turn for the better, he's become deeply
infatuated with Ashley, and tries to help her turn her life back around as he
struggles to win her heart.
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