For seventeen-year-old serial womanizer Fletch Colson, life is a game and if he plays by the rules, he'll win it all: his dream college, his parents' money, and a hot (if a little vapid) girl on his arm. Really, it couldn't be easier. All he has to do is get good grades, live a privileged boarding school life, and try not to mess up too much. However, when he accepts the seemingly impossible bet to change his ways and be "just friends" with smart, beautiful, tempting Ellie Jacobs - a girl who seems hell bent on confusing him - Fletch's whole world is turned upside down. Suddenly, what seemed simple and clear, no longer feels right and Fletch must decide if winning it all is worth losing a piece of himself.