Kelley Morse (CHRIS KLEIN) is an arrogant and impudent student at an upscale private academy who's set to graduate as the valedictorian, attend an Ivy league college and follow in the footsteps of his successful father, John Morse (STUART WILSON), who's just given his son a new Mercedes as his graduation gift.
Kelley's future seems bright until he and his buddies take the car out for a spin and end up in the nearby small town's local diner. There, while flirting with Samantha Cavanaugh (LEELEE SOBIESKI), the owner's daughter, Kelley evokes the wrath of her longtime, hometown boyfriend, Jasper Arnold (JOSH HARTNETT). After a brief altercation, Kelley and his friends leave, but not before insulting Jasper and his small town ways.
Not one to let things slide, Jasper sets out after Kelley in a car chase that ends up with them crashing into the diner's gas station, inadvertently burning down the diner, and getting into hot water with the law. Instead of having them serve time, however, the local judge sentences the two to help in rebuilding the diner. While that's no problem for Jasper, Kelley has no place to stay and even less desire to spend his summer in what he considers a backwoods community.
He does eventually agree to the sentence and an offer by Jasper's mother, Betsy Arnold (ANNIE CORLEY) for him to stay in their guest bedroom, but neither he nor Jasper or his dad, Malcolm Arnold (MICHAEL ROOKER), the construction foreman, are happy about the arrangement. As such, Kelley does his work, but refuses to have anything to do with the Arnolds.
His attitude about the small town begins to change, however, when he encounters Samantha once again, and the sparks immediately fly between them, much to the dismay of her parents, Jo (ANNETTE O'TOOLE) and Earl (BRUCE GREENWOOD), the town's sheriff. As the budding romance also understandably sparks anger and jealousy in Jasper, he, Kelley and Samantha enter into a romantic triangle that will soon change their lives forever.