Ashley Albright (Lindsay Lohan) is one lucky girl. Living in Manhattan, she just can’t seem to take a wrong turn. Jake (Chris Pine), however, is just the opposite, every step he takes landing him in trouble. When the rest of her team is caught in a broken elevator, and thus become late for a meeting with high profile music mogul and client Damon Phillips (Faizon Love), Ashley finds herself with the task of having to persuade him back to stick with her boss' company. She does so with remarkable ease, leading to a her landing a promotion. Jake, meanwhile, is attempting to score a meeting with Phillips, hoping to bring his attention to a band he is managing, McFly (themselves). But he is finding the task not easily achieved. Ashley is appointed to organize a charity masquerade ball for Phillips to help enhance his profile, and Jake has decided it's the perfect place to nab the music mogul’s time. There, both Ashley and Jake unexpectedly cross paths, and a mysterious kiss between the two leads to one getting the others luck. Ashley is in for an unpleasant surprise, while Jake's wildest dreams begin to turn to reality.