 A loser in life and love, Denton Baker 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 can win back the company that his father, Mr. Baker had stolen from him by a former friend, Mr. Lucas.With the help of his well meaning but overzealous best friends, Jackson Price, Ed McDoogle and Wiggins, Denton sets out to win the bet, which becomes even more difficult when he falls in love with his 2nd grade crush, Amanda Morrison.