Leon Harris isn't exceptional and he isn't popular. He's the kind of guy that peaked in middle school, when once upon a time he was in the "gifted" program and on the fast track to Ivy League glory.

Now, a high school senior, he's a complete slacker who spends his time hanging out in a third-rate ice cream parlor with his best friend, Stan, a guy who (jokingly, Leon thinks) claims to be Satan. Committed to his sloth, Leon panics when he finds out that Anna, the love of his life aka middle school girlfriend, might be moving back to town.

Determined to get his act together, Leon asks Stan for help. Stan gives him a few seemingly random and mysterious assignments. Date a popular girl. Listen to Moby-Dick, the audiobook. Find the elusive white grape slushee. Join the yearbook committee.

As each task brings Leon one step away from slacker city and one step closer to Anna, he starts to wonder if maybe he shouldn't have promised Stan his soul after all...