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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/97045/">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/81026/">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/81026/">Jasper during the "sentence", his attraction to Samantha is immediate and strong, which angers Jasper/81026/">Jasper, who's known Samantha for years.