The film opens in 1987 with Nicolas Cage and Tea Leone at an airport. Cage is leaving on a one-year internship at a prestigious British bank in London to further his career. She tells Cage she has a bad feeling about it and does not want him to go. She is worried about how it will affect their relationship. He says that they have discussed it before and shouldn't change their plans with a quick decision.

The movie then jumps to the present and Cage is in bed with a beautiful woman. (Not Tea Leoni) He is now working for a large wall street firm and is a man of high ranking. He is a master wheeler dealer. He is wealthy….. and single.

On Christmas Eve he gets a telephone message from Tea Leone to call, but decides against it. One of the men he works with says, old romances are like old IRS files…. You file them away for 3 years then throw them out.

Cage decides to walk home that night and stops at a small store to buy egg nog. While in the store, Don Cheadle enters and tries to claim a winning lotto ticket for $238. The clerk refuses saying the ticket has been fixed. The man pulls a gun. Cage walks over to the man and using his great negotiating skills, he offers to buy the ticket for $200. Cheadle and Cage walk out of the store talking. Cage actually offers to help the guy get his life back in order and asks the man what he wants, after all, "Everybody wants something…" Cheadle asks Cage what he would want and Cage answers… "I have everything I want and need" At that, the Cheadle kind of laughs and says, just remember, you brought this on yourself. With that, he walks away.

The next morning when Cage wakes up, he discovers he is in some sort of parallel universe and he is in bed with Tea Leoni. It's Christmas morning.

A child runs into their bed and is begging to open Christmas presents. Cage is completely confused. He discovers that he has been married to Tea for 13 years and has two kids. Turns out that 13 years ago when he got to London, he came back the next day. His career never took off because Tea's father had a heart attack and although he lived, Cage took over his tire business.

Through a series of difficulties and experiences, he grows to love Tea and his children and by the time he discovers how much they truly mean to him, Don Cheadle reappears. Cage knows that he is going back to his original life.

The last scene of his "dream life" is he just watching Tea sleeping.

The next time we see him, he is waking up in his old apartment. He is once again a wealthy business entrepreneur. It is Christmas day and he goes to the office to talk with his people trying to calm their worries about an impending merger. He is going to fly to Denver to seal the deal.

On the way to the airport, he can't stop thinking about Tea. He goes to her apartment and finds her and several men busy packing all her belongings. She is leaving for Paris. Her law firm is opening an office in France. Instead of being the poor, nonprofit lawyer that he saw in his dream, she is a very wealthy, definitely for-profit lawyer. It seems that the reason she called him was to give him a box of his belongings from 13 years ago.

He takes the box back to his apartment and while looking through it, decides he has to stop her from going to Paris. He rushes to the airport, finds her in the concourse where she is in line, about to get onboard. He begs her not to go and to stay and have coffee with him. She says she's sorry that he has not gotten over their relationship but she has.

Cage starts explaining to her all about his dream and the two wonderful children and how he loves her and their magnificent life together.

She listens to his whole story and accepts his offer of coffee. The final scene is the two of them sitting at the airport coffee shop, talking.