The New Rules of High School by Blake Nelson

Max is the consummate high school overachiever. Straight-A student, debate team captain, future editor of the school paper, dutiful Max does what's expected, until the day he inexplicably breaks up with Cindy, his perfect girlfriend. Is their relationship too much to handle on top of everything else? Or is Max just tired of doing everything he's supposed to? As Max begins to question his life, all of the old rules dissolve-and he searches in some very unlikely places for new ones. "Nelson, it seems, possesses that peculiar and particular ability, granted to only a few-the Judy Blumes and J. D. Salingers of this world-to accurately portray the mysterious inner life of the American teenager."
-Time Out New York
"Fiercely real and really fierce."
-Daniel Handler (aka "Lemony Snicket")