Two Cool Guys follows the off-beat coming of age story of Allen Parker and John Sharp, two guys who really aren't that cool. While Allen tries fruitlessly to become socially cool, John puts on a calm exterior while feeling internal strife at the problems of a two year relationship with his girlfriend Rachel. Allen is surprised to find that long-time classmate Ellen is not only amused by him, but possibly taken by his strange personality. As Allen hopes to finally be accepted for his quirky self, John seeks emotional freedom from his restrictive relationship; both desiring the 'coolness' they seek.