Buddy Amaral (Ben Affleck), a cocky, self-absorbed ad executive who--in desiring a tryst with the gorgeous Mimi (Natasha Henstridge), a woman he meets at the airport--gives up his plane ticket back to Los Angeles to writer Greg Janello (Tony Goldwyn). The plane crashes, and Buddy begins a downward spiral of alcoholism and self-loathing until he undergoes rehab. Once out, he decides to pay a visit to the dead man's widow. Abby Janello (Gwyneth Paltrow) is a struggling real estate agent with two young sons. She slowly befriends Buddy and falls in love with him while Buddy struggles with the guilty secret of his connection to her husband's untimely death which could destroy their relationship.