"The Black Book (Diary of a Teenage Stud)" by...
This is book one is a series of books about Jonah, a high school junior. The books are his diary, stating in his words what his life is all about. Jonah is back in public school, a year behind all of his friends, after a disastrous end to his last year in private school. The specifics of the trouble at his private school are a secret Jonah won't reveal to his friends or to the reader. As if his situation weren't difficult enough, Jonah's mother is too busy with her new life as a sex expert for teens, with a book and a radio show, to worry about Jonah's problems.
Jonah is a pretty typical teenager, dealing with family, school, girls and a lack of self confidence. He lives largely in a fantasy world, but his style and thoughts are compelling and something teens will be able to relate to. Beware, though, that this book leads right into the next one in the series, which is sort of a dirty trick to hook a reader without resolving the plot points.