Stranded in Chicago's O'Hare Airport one snowy night, Buddy Amaral (Ben Affleck) shares a table in a crowded bar with Mimi (Natasha Henstridge), a Dallas-bound businesswoman and Greg Janello (Tony Goldwyn), a scriptwriter anxious to return to his family in LA. Believing the storm will prevent anyone from getting home that night; Greg accepts the airline's offer (sweetened with some free tickets) to exchange his seat for passage home later the next day. When the flight is called a short while later, Buddy who is also headed for LA, generously offers his ticket to Greg. The smooth-talking, womanizing Buddy can see some advantages to spending the night in Chicago, considering Mimi is stuck there too.
But what seemed to be a mutually beneficial opportunity turns into a tragedy after Greg's plane crashes, leaving no survivors. Because Greg was using Buddy's boarding pass, there is also some confusion about who was on the plane. Although realizing it was just lucky coincidence that he was not in the accident, Buddy tries to deny any responsibility for Greg's death. Turning to alcohol, he puts his career as an ad executive in jeopardy.
Even after rehabilitation, it takes pressure from his new assistant Seth (a homosexual and a recovering alcoholic) to get Buddy to live up to his A.A. promises, such as trying to correct any harm he has caused others. Recognizing he can only resolve his feelings of guilt by facing Greg's widow, Buddy meets Abby (Gwyneth Paltrow), but is unprepared for her simple charm. And when he finds his sympathy being replaced by true affection, he's even more reluctant to tell her the truth.
This quiet romance contains several characters with good intentions that often make bad decisions. Buddy's few moral convictions quickly entangle him in a net of lies, while Abby chooses to engage in a sexual encounter with Buddy before there's any intention of a serious relationship. Scattered throughout are terms of Deity and a sexual expletive. While positive growth and consequences are depicted, these negative elements take a lot of the bounce out of this film.