Ashley (Lohan) is the luckiest girl in New York City, where she has a promising career and a life full of glamour and romance. Jake (Pine) is the unluckiest guy in town, tormented by constant mishaps and missed opportunities. Everything changes for Ashley and Jake when they meet at a swank masquerade party, share a kiss, and a miraculously swap their luck. Now Ashley's ultra-fabulous life is going completely sour while Jake is finally living large. But Ashley is determined to track him down and steal her luck back.