Prep, by Curtis Sittenfeld
I just finished Prep, all about a girl's experience at Ault School (largely based on the author's alma mater, Groton). I often found it heartwrenching to follow Lee through her self-conscious high school years. It's told by her about 10 years after she finishes high school, which allows for some self-reflection. But her wishing she had been different in high school is almost worse than simply letting her high school self stand on her own. Most of the book was reminiscent of my own prep school experience at Milton, and even some of Lee's painful social moments were familiar, but the book represented an extreme example of teenage angst.