Buddy (Affleck) has just signed an airline in Chicago as a big client, but is ironically delayed at the airport waiting for a flight to LA on that same airline. He meets fellow passenger Greg, who opts to be bumped, even though it means missing an activity with his older son. When the flight gets resumed, Buddy thinks he's doing a good deed by swapping tickets with Greg so he can get home to his son. Sadly, the flight crashes. Buddy conspires with his friend, the ticket agent that night, to take his name off the passenger list and put Greg's on. Once he's back in LA, his new client dictates that the company run a series of feel-good ads about the crash. Buddy feels very hypocritical, and completely loses it when the commercials win a Cleo. After going through re-hab, he decides he needs to check on Greg's widow. But he doesn't plan on falling in love with her.
Just prior to Christmas, O'Hare Airport in Chicago is snowed in, delaying flights in and out during which time many stranded passengers at the airport connect with each other, such as Los Angeles based ad man Buddy Amaral, Los Angeles based struggling writer Greg Janello, and Dallas based Mimi Prager. When Buddy's Los Angeles destined flight on Infinity Airlines is about to leave - the Chicago based airline which Buddy has just signed as a client - Buddy, in what he believes is a win-win situation, offers his ticket to Greg, who is trying to get home earlier to his family: wife Abby Janello and their young sons, Scott and Joey. However, early in the flight, it crashes, killing all on board. In the aftermath, Buddy's life quickly spirals downward out of control as he turns to the bottle, unable to deal with the guilt associated with how his innocent action saved his life but destroyed that of the Janellos. Going through therapy, Buddy feels the need to make amends by helping Abby without telling her about his connection to Greg. Buddy finds that Abby too is not coping well, telling white lies as a measure to deal with her grief, while not fairing well in her new job as a real estate broker. Following his good deed, Buddy tries to stay away from Abby knowing that nothing can come out of being with her because of his history with Greg, but with a little help from Buddy's new assistant Seth, Buddy and Abby fall for each other. The question becomes if there truly can be a future for the two of them either if Abby finds out the truth or if Buddy can deal with forever hiding the truth from her.
A man switches plane tickets with another man who dies in that plane in a crash. The man falls in love with the deceased one's wife.
- Buddy Amaral (Affleck) is an ad-man who, while waiting for his flight to meet with a client, meets a laid back family man, Greg (Goldwyn) awaiting another flight home to his family. When Buddy encounters a beautiful woman, Mimi Pager (Henstridge), and becomes enamored with her, he arranges to swap tickets and flights with Greg so that Greg gets home early and Buddy can have extra time with his new lady friend, figuring he's doing a good thing while serving his own needs. Buddy's "good deed" backfires horribly when the flight he bumped Greg to crashes, and Greg dies. Buddy is so guilt ridden over this that he eventually collapses into alcoholism. Sometime later Buddy re-emerges from rehab but guilt still haunts him, so in an attempt to redeem himself he tracks down Greg's widow, Abby, (Paltrow) and tries to help her and her children any way that he can, even though he does not tell her it was his fault her husband died. Things become complicated when the guilt-ridden ad-man and lonely widow fall in love.
Buddy keeps quiet about how he met Greg at the airport and how he gave him his own ticket. But one day Mimi Pager suddenly shows up at Abby's doorstep with a video tape of her, Buddy and Greg at the airport. When she realizes the role Buddy has played, she breaks up with him. The families of the passengers on the crashed jet have taken the airline to court and Buddy must appear as a witness. At the stand he takes the opportunity to explain about the guilt he has felt ever since the crash. Abby watches the court proceedings on TV and decides that she can forgive him.