Ashley (Lindsay Lohan) is the luckiest woman in New York City while Jake (Chris Pine) is one of the unluckiest men, with one bad event happening after another. After kissing Jake at a masquerade ball she organized for a client, Ashley realizes she's swapped her good fortune in turn for Jake's bad luck. Ashley breaks her shoe, rips her dress, loses her job and her apartment, while Jake receives a brand new apartment and a record deal for his band, McFly. Ashley tries to find Jake again to kiss him and therefore regain her luck. However, Jake was masked, so she does not know what he looks like so she kisses all men who could be him (including all the male dancers at the ball, whom Jake was pretending to be in order to get into the ball), and tests whether he is the right one by scratching a gambling scratchcard. After giving up, they meet in a cafe after Ashley is covered in mud and has no money for food. Jake feels sympathy for Ashley because he has been unlucky himself. After a while she realizes that it was Jake who was at the ball, and regains her luck by kissing him again. Later, at a concert managed by Jake, where things go wrong due to Jake's newly regained bad luck, she feels sorry for him and kisses him again to transfer the luck. Ashley has feelings for Jake, but thinks that a relationship would not work because they would have to kiss. She is about to leave New York to visit her parents for a while when Jake shows up at Grand Central Station after finding out about the kisses transferring luck. He convinces her to stay and says having her is worth more than being lucky all the time. Eventually they both kiss Jake's younger cousin on opposite cheeks at the same time, thus transferring the luck to her.
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