In the summer between high school and college, a love triangle is created between a private school student, a girl from the 'wrong side of the tracks' and her boyfriend. While out for a cruise in his new Mercedes, Kelley Morse (Chris Klein) stops into a local diner, owned by Samantha's (Leelee Sobieski) mother. While there, he clashes with Samantha's boyfriend Jasper (Josh Hartnett). The two get into a race that ends with a car crashing into the diner.
Their punishment is to fix the diner. Although Kelley intends to have nothing to do with Jasper during the "sentence", his attraction to Samantha is immediate and strong, which angers Jasper, who's known Samantha for years.