In New York City, Ashley Albright, Lindsay Lohan, a public relations executive at Braden & Co., has enjoyed extraordinary good fortune since childhood, while Jake Hardin, Chris Pine, an aspiring music producer who works as a janitor, endures a string of daily misfortunes. Jake manages the British band McFly and has been struggling to get their demo into the hands of Damon Phillips, a sharp record executive who could change the band’s fate.
At a glamorous masquerade ball hosted by Ashley’s firm, Jake sneaks in hoping to meet Phillips. A mysterious fortune teller at the event prophesies that Ashley’s luck will soon shift. During the ball, the two share a dance and a kiss, and unknowingly swap their fortunes—their lives begin to tilt in opposite directions.
After the kiss, Jake saves Phillips from a dangerous collision, and Phillips takes the McFly demo seriously, deciding to work with the band. Meanwhile, Ashley’s world falls apart: she’s arrested with her boss, Peggy, when an invited guest is revealed to be a prostitute; she loses her job, and her apartment is condemned due to flooding and mold. With nowhere else to go, she moves in with friends Maggie and Dana.
Desperate to reverse the reversal of fortune, Ashley contacts the fortune teller, who explains that someone else’s luck is needed to restore balance. She concludes that the masked stranger she kissed must hold that luck. Jake’s life begins to improve, while Ashley desperately tries to reclaim her luck by kissing every male dancer from the ball—without success. A breakdown at a diner leaves her drained, and Jake—unaware of who she truly is—offers her a job at the bowling alley he just left.
The two become friends, and Ashley introduces Jake to Maggie, a singer-songwriter. He decides to feature Maggie’s song in an upcoming McFly concert at the Hard Rock Cafe. Ashley overhears Jake telling someone that his luck changed after the masquerade; realizing he was the masked dancer, she kisses him again and regains her own luck.
Peggy offers to rehire Ashley if she helps with a crucial client meeting. Ashley discovers Maggie’s song has been pulled from the concert lineup, and Jake and McFly begin to suffer more misfortune. Ashley skips the meeting and goes straight to the concert venue, where she kisses Jake and transfers the luck back to him. The concert goes on, and Maggie’s song is performed to cheers.
With departure looming, Ashley prepares to leave New York. Jake finds her at Grand Central Terminal and admits that he was the lucky masked dancer; he says he’s willing to give up his luck to be with her. They kiss again, and their fortunes continue to shift in tandem. When their friend Katy arrives, they all kiss her on the cheeks, transferring some of the luck to her. Katy ends up winning a $25 lottery ticket. As Jake and Ashley walk outside together, a burst water pipe erupts, bursting around them as they step into the next chapter of their intertwined lives.
