Just My Luck (2006)

Synopsis
Two people discover just how true the old adage "lucky in life, unlucky in love" can be in this romantic comedy. Ashley (Lindsay Lohan) has always been the sort of girl fortune smiles upon -- she's pretty, she has a great job, she had 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 at a bowling alley. 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. Just My Luck also stars Samaire Armstrong, Faizon Love, and Tovah Feldshuh. ~ Mark Deming, All Movie Guide