Ashley Albright (LINDSAY LOHAN) has been lucky all of her life. Whether it's avoiding the rain, getting an elevator all to herself or meeting some handsome guy, things always seem to go her way, much to the amazement of her friends Maggie (SAMAIRE ARMSTRONG) and Dana (BREE TURNER). They all work for Peggy Braden (MISSI PYLE) at her PR firm, where lady luck visits Ashley once again.
Music mogul Damon Phillips (FAIZON LOVE) and his entourage have arrived for a meeting with Peggy, but when she and everyone else ends up stuck in the elevator, Ashley takes it upon herself to pitch an idea to him. He loves it, Peggy is impressed, and soon Ashley is planning a swanky party, and even asking her handsome neighbor Antonio (CARLOS PONCE) to be Peggy's blind date.
If only things went so smoothly for Jake Hardin (CHRIS PINE). A bowling alley employee who spends time with his fourth grader cousin Katy (MAKENZIE VEGA) when not serving as the audio mixer and manager for the British band McFly, he's been trying to get a demo into Damon's hands. But, being the unlucky sort, he doesn't have a chance.
That is, until he inadvertently crashes Ashley's masquerade party as one of the hired dancers and tries to meet Damon. That doesn't happen until he and Ashley end up kissing on the dance floor. Suddenly, all of her luck is transferred to him, he ends up saving the mogul's life, and Ashley loses her job when the party takes an unexpected turn for the worse.
Once Ashley realizes what happened, she tries to find the masked dancer who kissed her and stole all of her luck, unaware that Jake isn't one of them. From that point on, and as their paths cross once again, the two try to deal with their ever-changing luck.