When D-Roc sees a pair of expensive sneakers called Air Jareds, he wants his mother to buy them to wear at school in order to look cool. His mother purchases a cheaper priced pair of Air Johnsons instead. Afraid of looking bad to his crew, D-Roc asks Soo-Young to make Air Jareds out of Air Johnsons and when they work out well, they realize they can make money by converting the shoes. Their plan to make money eventually goes wary and D-Roc is taught a lesson about being himself.

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.