Ben Holmes (Affleck) is a New York writer on his way to Savannah, Georgia for his wedding to Bridget (Maura Tierney), however, when his plane is about to take off, a bird flies into one of the engines, causing a flameout, so he reluctantly agrees to travel with Sarah (Bullock), a free-spirited drifter who was also on the plane and who also needs to get to Savannah within a few days. During the course of their trip, luck seems to want to prevent them from getting to their destinations. However, Ben is impressed by Sarah's fun-loving personality, and starts to form a close bond with her. As they get nearer to their destination, Ben starts reconsider his engagement.
This film features examples of:
- Bittersweet Ending: Ben and Sarah do not end up together, but Ben and Bridget still agree to get married since they realize they still love each other, and Ben's experiences with Sarah are still shown as having helped him become a better person.
- Uptight Loves Wild: Ben is a straight-laced writer who is impressed by the fun-loving personality of free-spirited drifter Sarah, forming a close bond with her and starting to wonder if he's making the right choice in getting married.