She's All That (1999)

Zack is the reigning stud of Harrison High School, and everyone thinks his match with princess Taylor will last forever. When Taylor dumps him for an obnoxious star of "The Real World", Zack is devastated. But he rebounds, betting his friend Dean that he can turn any girl into a prom queen. Dean chooses Laney, a geeky outcast who worries about Bosnia and spends her days painting in her basement. Laney has no time for Zack, but he persists and as time goes by, the two find themselves friends. Rather than raising her to his social level, Zack finds himself falling hard for non-conformist Laney.