Pizza: The Movie (2004)

Three years since graduating, Kevin Miller is still stuck on his high school crush. When she returns to town on break from college, he realizes this is his last chance to win her heart, only she doesn't even know he exists. With the help of his inept and sometimes annoying best friend Barry, he develops a plan to make it happen, only for it to work, he'll have to give up his comfortable boring life and step into the crazy world of pizza delivery.