Trippin' (1999)

Greg Reed believes he can get through high school by bedding the prom queen, committing two-bit thefts and working part-time at a rib joint. The only effort he exerts is when creating elaborate sexual fantasies about the object of his obsession -- the beautiful, and seemingly unattainable, Cinny Hawkins. However, when he realizes that that way to win Cinny's heart is through academics, Greg stops day dreaming and hits the books, upping his chances with his dream girl and gaining the confidence to pursue other important goals, namely attaining a higher education.