Ashley Albright (Lindsay Lohan) is the luckiest woman in the world, a person to whom all the good things in life have come far too easily. She can pick a lottery ticket at random and hit the jackpot. In New York, the world's busiest city, Ashley never has to wait for a cab. And she has a terrific job as an account exec at a prestigious public relations firm. Everything goes Ashley's way. And now, she's been given a great opportunity to advance her career: she is to plan a masquerade ball in downtown Manhattan for record mogul Damon Phillips (Faizon Love) and his company.
Jake (Chris Pine), on the other hand, is a bad luck magnet. His skies are always raining; his pants are always on the verge of splitting at the seams. His job is cleaning toilets at a bowling alley. But even a steady bombardment of catastrophes doesn't dim Jake's dreams. He thinks he may have his chance at the brass ring with his discovery of a rock band McFly. If Jake can keep his bad luck at bay for just one night, he'll sneak into a masquerade ball and get McFly's CD into the hands of music titan Damon Phillips.
On this night when dreams can be made or broken, fate brings Ashley and Jake together on the dance floor. Instantly taken with one another, they share an electrifyingly kiss -- and with that one kiss, their luck switches places.
Suddenly, Ashley's dress rips. Her heel breaks. Her good luck seems to have finally run out. Jake, in his rush to catch Phillips before he leaves, ends up saving the record mogul's life and earning with that one simple twist of fate, the chance to make all his dreams come true.
As Ashley desperately races to regain the luck she blithely took for granted, she begins to see that it's not so much having good luck but what you do with it that counts, and that her greatest chance of redemption lies with the guy who holds the key to her sudden change of fate.