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Movies like Kingston High (2002)

Regretting his lack of high school "extracurricular" activity and skipping out on his senior prom, Sketch (Jeramie Gladman), a textbook misfit, tries to make up for lost time via one night of unadulterated partying. Stifling his insecurities, he makes a bet with his pals that he'll win the love of a girl who's been the object of his affection for the past four years.