It's his senior year, and Will Shea has conned his way into one of the country's most elite prep schools. But he soon runs into Andrea, a fellow con artist. With the school not big enough for the both of them, they make a bet that whoever can con Brandt Rush, the richest, most privileged student in the school, out of $50,000 gets to stay at the school. Will starts setting up his con with his uncle, who's one of the best grifters in the business, and with the unwanted help of his father. The plot thickens as Will starts falling for fellow student Gatsby, and some of Will's lies start to catch up with him.