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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, h