Book? Pfeh. The entire Hope series by David Feintuch. Short version: Guy is raised by a crappy, abusive single dad to be a jerkass and think of himself as an absolute shit. He saves the day several times, persists in thinking the worst of himself and is never, ever happy or ever feels better about himself. The End. Wash, rinse and repeat 8 times.
As an example, at one point in one of the books, he kisses a girl he likes. It's okay, but he thinks of himself having "molested" her because he didn't ask her permission first. And it's just a closed-lips peck! I was like Huhwha?