Down on his luck, Denton Baker (Alex Klein) gets into a high stakes bet where he has one summer to find, and hook up with, every girl he had a crush on from 1st to 12th grade. If he succeeds, he wins back the company that was stolen from his father (“Diamond” Dallas Page) by a former friend (Jake “The Snake” Roberts). But when Denton falls in love with his 2nd grade crush, he and his father risk losing the company forever.