On a dare, a rich college student named Kelley Morse (played by Chris Klein) and his friends stop at a country restaurant called The Wagon Wheel during a road trip. While there, Kelley meets Samantha (played by Leelee Sobieski), the daughter of the restaurant's owner. Despite her initial reluctance, the two quickly begin a relationship.
One night, Kelley takes Samantha's father's antique Porsche for a joyride, which ends in a crash that destroys the restaurant. In an attempt to make amends, Kelley and his friends decide to rebuild the restaurant themselves, using the incident as a lesson in responsibility and caring for others.
As they work together, Kelley begins to realize the value of hard work and the impact his actions have on people's lives. Meanwhile, Samantha is torn between her loyalty to her family and her growing feelings for Kelley.
The film explores themes of socioeconomic differences, responsibility, and the power of love to transform people's lives. It ultimately ends with Kelley and Samantha's relationship being tested and a decision that will determine their future together.