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The Family Man
Jack and Kate, who have been together since college, are at JFK Airport, where he is about to leave to take up a twelve-month internship with Barclays in London. She fears the separation will be detrimental to their relationship and asks him not to go, but he reassures her that their love is strong enough to last and that the internship will be beneficial to their future together.
Thirteen years later, Jack is a wealthy bachelor and Wall Street executive in New York City, with millions at his disposal. At work, he is putting together a multi-billion dollar merger and has ordered an emergency meeting on Christmas Day, disregarding his employees' desires to spend time with their families. In his office, on Christmas Eve, he gets a message to contact Kate. Jack ponders whether Kate is attempting to reconnect, but chooses not to return her call.
On his way home, Jack is in a convenience store when a young man, Cash, enters claiming to have a winning lottery ticket worth $238, but the store clerk refuses him, saying the ticket is a forgery. Cash pulls out a gun, and Jack, trying to defuse the situation, offers to buy the ticket, calling it a “business deal." Cash eventually agrees.
Outside, Jack patronizingly tries to help Cash, who, feeling like he is being preached to, asks Jack if anything is missing from his own life. When Jack haplessly says he has everything he needs, Cash enigmatically remarks that Jack has "brought this upon himself" and walks away. A puzzled Jack returns to his penthouse to sleep.
Jack wakes up the next morning on Christmas Day in a suburban New Jersey bedroom with Kate and two children. Confused, he rushes out to his home in New York, but the doorman and his neighbor claim not to recognize him. He goes to his office, which is closed for the holiday, and is turned away by security. Outside, he encounters Cash, now smartly dressed and driving Jack's Ferrari. Although Cash offers to explain what is happening, all he does is make a vague reference to "the organization" and tell Jack that he is getting "a glimpse" of something that will help him to figure out for himself what is important in life.
Jack returns to the house and tries to tell Kate the truth, but she reacts angrily. He receives some help from his young daughter, Annie, who believes Jack is an alien and her real father will soon return. He struggles to adjust to fatherhood and his modest family life, finding that he is a tire salesman working for Kate's father and Kate is a non-profit lawyer. When he discovers this is the life he would have had if he had stayed in the U.S. as Kate had asked, he lashes out at Kate and expresses resentment for her holding him back.
Jack later apologizes and grows closer to Annie and her baby brother, Josh, and realizes he never fell out of love with Kate. He comes to enjoy his family life and begins succeeding at his sales job. One day his former boss, Peter Lassiter, comes in to have a tire blowout fixed. Taking advantage of the chance meeting, Jack uses his business savvy to impress Lassiter, who invites Jack to his office, where Jack worked in his 'other' life.
There, after a short interview, Lassiter offers him a position. While he is excited by the potential salary and other perks, including a lavish apartment in Manhattan, Kate is less certain. She expresses deep misgivings about raising their children in the city and leaving their old life behind, telling Jack that they should be thankful for the life they have.
Jack returns home only to discover his plane ticket to London. Upon closer examination, he realizes that he did in fact take the flight, but then came back the next day to be with Kate. Reminded of Jack's choice, she reciprocates his feelings by telling Jack that she is prepared to follow him and move the family to the city in order to do just as Jack did for her.
Jack encounters Cash at a grocery store and is frightened by the idea of leaving this life, which he now loves, behind. Cash reminds him that a glimpse, by definition, is an impermanent thing. Jack returns home again and watches over his children and then tries to stay awake while watching Kate sleep but eventually does fall asleep and wakes to find he has returned to his old life, on Christmas Day.
Jack returns to the office to close the big acquisition deal, making plans to fly to Aspen to prevent it from failing, but first visits Kate, now an unmarried corporate lawyer, preparing to move to Paris. She only called him to return a box of his old possessions, and when Jack asks her to meet for coffee, she suggests that he look her up if he's ever in Paris.
Jack chooses not to go to Aspen and instead chases after Kate to the airport and begs her to stay. She reacts with confusion, as their relationship has been over for more than a decade, and refuses. Jack then describes in detail their life together and their children, saying it was a dream that seemed real and admitting that he can no longer conceive of a life without her. Intrigued, she eventually agrees to go with him for a coffee. From a distance, they are seen talking inaudibly and laughing over their coffees and their possible future.