Project Weekling (2013)

Carlos is a socially-inept preteen who has a long-time obsessive crush for Cheryl, the quiet, achieving student suddenly turned campus sweetheart. One day, he writes in his diary that he has made an important decision: he is going to try to ask for Cheryl's hand in the course of one week, amidst the enormous odds against him presented by his timid calculating personality and by the gang of machismic school jocks, whose leader has his eye on Cheryl as well.