By Curtis Sittenfeld. Published in 2005.

Am I ever going to get to the point where I can read about the torments of adolescence without suffering flashbacks? I couldn’t ever make it through more than 10 pages of Curtis Sittenfeld’s story of a hyper-self-conscious teenage girl without having to set the book aside for a while, to remind myself that I’m 26 now and should be past this stuff.

Prep, Sittenfeld’s debut novel, has its faults. The plot meanders lazily, and Sittenfeld sometimes relies too heavily on stereotypes when sketching minor characters. That said, her portrait of the neurotic loner as a young woman is so spot-on, so well-observed, so fully realized, that it makes the book’s flaws look utterly inconsequential.

Lee Fiora, the protagonist, grows up in a solidly middle-class home in the Midwest and wins a scholarship to attend an elite boarding school, starting in ninth grade. Her reasons for wanting to attend boarding school are somewhat murky, and once enrolled, she never truly enjoys the experience. Relentlessly self-critical, convinced of her own lack of comparative worth, Lee is the kind of girl who looks with suspicion upon a guy who shows interest in her because she believes he has no legitimate reason to show interest in her.

In a lesser book, Lee’s failure to fit in would reflect her superiority to her lesser classmates, but Sittenfeld refuses to indulge in such easy answers. Lee isn’t an artsy type unable to thrive in a conventional setting. She’s not a brilliant student who intimidates her classmates. She’s not even the Holden Caulfield–wannabe, refusing to play games with the “phonies.” She is merely a perceptive but faint-hearted girl who is agonizingly conscious of social mores and rules but unable to summon the courage and creativity to play the game well, however much she might wish to. And she does wish to. Her insight extends only far enough for her to understand the tangled webs of teenage relationships, not far enough for her to understand that ultimately those webs won’t matter much.

In other words, Lee is an all-too-typical teenager. She’s not an adult woman’s romanticized vision of her former self. She’s snobby, craven and myopic. Her obsession with social status affects every decision she makes, including how she treats her friends and her family. She’s not particularly admirable and, sometimes, not even likeable. And yet Lee is so recognizably human — and so vulnerable — that Sittenfeld draws our sympathies to her, despite her myriad faults.

Besides being a remarkable character study, Prep also is a fascinating exploration of the unspoken, unacknowledged effects of class differences in American society. Being relatively poor in comparison to most of her classmates is central to (though not solely responsible for) Lee’s inferiority complex, particularly toward the end of the novel, when a major indiscretion destroys her carefully crafted persona. Here, too, Sittenfeld excels at showing how people craft identities and how fragile that work can be.

Prep is compassionate in its tone but merciless in its unflinching depiction of how petty and cruel and shortsighted teenagers can be. No romantic nostalgia clouds the sharp clarity of Sittenfeld’s storytelling, and that, of course, is why it’s so painful to read. Of course, I — having been a hyper-self-conscious teenage girl myself — am particularly vulnerable to that sort of thing, but Sittenfeld deserves credit, too. Prep strips away the distance maturity brings and forces us to relive emotions we might prefer to forget. That’s a mark of great writing, not just my great neuroses.

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