Jack Campbell (Nicholas Cage) has it all. He is a successful workaholic stockbroker in New York City. He has a posh high-rise apartment, a nice car, tons of money, noncommittal relationships with beautiful women, and all the fine food and wine he could want. On Christmas Eve Jack is still working, and he gets a message from his secretary that his old college girlfriend Kate (Tea Leoni) called. Jack and Kate were engaged in college, but he chose his career over her. After throwing away her number thinking it's better to leave the past alone, Jack goes to sleep and wakes up living the life he would have had if he'd chosen Kate over his career. They are a working middle-class couple with two kids and a minivan: they don't enjoy the high life but they have an incredibly happy life. When he wakes up from this alternate life and finds himself back in his high-rise apartment, Jack is suddenly unsatisfied with his current life. He races to find Kate before it's too late to see if she will give him a second chance at the life they could have had together.