Trippin'(1999)

He's a legend. In his own mind.

Greg is near the end of his senior year in high school, wanting to go to the prom, eyeing Cinny (the school's beauty with brains) from afar, and regularly trippin', daydreaming about being a big success as a poet, a student, a lover. His mom wants him to apply to colleges, but Greg hasn't a clue. One of his teachers, Mr. Shapic, tries to inspire him, too. He finally figures out he can get close to Cinny if he asks her for help with college applications. But friendship isn't enough, he wants romance and a prom date. So, he tells a few lies and, for awhile, it seems to be working. Then, things fall apart and Greg has to figure out how to put the trippin aside and get real.