The movie starts off promisingly enough. Successful businessman, Buddy Amaral, played by Ben Affleck, leads a shallow, sophomoric existence. Failed playwright, Greg Gennello, played by Tony Goldwyn, is happily married and has a rich family life. Their worlds collide when they meet in an airport and get to talking. Both headed to the same destination, Greg wants to get home to his family but is bumped from his flight, while Buddy wants to miss that very same flight so that he can have a one night stand with a beautiful fellow traveler.
In a moment of wild abandon, Buddy gives his ticket to Greg who then boards the plane in his stead. Unfortunately, this act of seeming generosity by Buddy has dire consequences, as the plane crashes and Greg is killed. When Buddy later discovers this turn of events, it is a moment of reckoning for him, and he goes into a personal downward spiral.
A year later, after a stint in rehab to get his drinking under control, he seeks out Greg's widow, Abby, played by Gwyneth Paltrow. Still feeling guilty over Greg's death, Buddy seeks redemption by doing something nice for Greg's widow, who, as the single parent of two young boys, is now trying to make ends meet as a real estate agent. He gives her a sizable real estate commission to handle, though she is unqualified, and soon they begin dating and fall in love. At this juncture, Buddy has still not told her that their meeting was not kismet.
To make a long story short, Abby discovers, in a rather unpleasant way, the part that Buddy played in Greg having been on that fatal flight. The movie then goes south. What had started out promisingly enough, takes a strange twist. While there is, undeniably, chemistry between the two stars, which explains their off screen romance, their sizzle is not enough to keep this movie on even keel, and the movie begins to flatline. Notwithstanding the eleventh hour fizzle, however, it is still a moderately enjoyable movie.