As a partner in LA’s hippest advertising agency, Buddy Amaral (BEN AFFLECK) makes things happen. Fearlessly confident and wildly charming, his clients love him, and thanks to his killer good looks, so does every woman he meets. Life smiles on Buddy… that is until the December night he’s stranded in a major snowstorm at Chicago’s O’Hare airport.

There, Buddy meets Greg Janello (TONY GOLDWYN), who is trying to make it home in time to celebrate Christmas with his family, and beautiful business woman Mimi Praeger (NATASHA HENSTRIDGE). When Buddy’s connections get him a seat on the only flight out that night, he’s faced with the choice of either getting on the plane or enjoying a one-night tryst in the windy city. Buddy picks the sexier option and generously offers Greg his seat.

But the next morning, Buddy learns that the plane he should have been on has crashed, and for the first time in his life the guy with all the answers is at a loss. Compelled to make things right, Buddy sets out to find the wife (GWYNETH PALTROW) of the man who took his seat. It’s a bold move that will change the lives of two people who never in a million years would have met, in very surprising, unpredictable and ultimately unforgettable ways.