Gimlet-Eyed Girl Grows Up; Preppies Poked and Prodded

Prep , by Curtis Sittenfeld. Random House, 406 pages, $21.95.

Yo, prep-school papa! You with the gray hair and rueful smile, dropping your little bundle of neuroses off at her boarding school after the long Christmas break. You think no one was watching? You think no one saw how you jumped on the cell to your mistress before you were even down the cobblestone drive? Think again. Could be that a gimlet-eyed novelist posing as a 14-year-old student was checking out your every move.

Not that parents are the only ones who land under the feverishly microscopic lens of Curtis Sittenfeld, now all grown up, a graduate of the Iowa Writers’ Workshop and the author of a big-buzz debut novel, Prep. Also in her sights is a newbie teacher who comes in for a compassionate drubbing because she has the misfortune to sport a frumpy accessory. An overweight classmate falls into empathetic disfavor not because of the extra poundage, but because she feels more secure than she has a right to. The smirkiness of another classmate is kindly judged to be only skin-deep: Her smugness was “like the earth’s crust; once you got below it, she was strangely innocent.”

Clearly, the narrator of Prep is incapable of missing a trick. Fresh from Nowhere Indiana, trying desperately to blend into the woodwork of her exclusive Massachusetts boarding school, Lee Fiora is the last person you’d expect to be able to see through appearances. (In real life, the author hails from Cincinnati-which makes sense. Ever notice how Ohio girls are the ones most enamored of the East Coast? Victims of the so-near-yet-so-far syndrome.) Unwealthy, awkward, obsessively attuned, Lee is inexperienced with taxis, can’t pronounce “Greenwich,” doesn’t know Bob Dylan from Bob Marley; she’s a Hoosier hick whose dad wears mismatched khakis (and is the more pitifully lovable for it). But it’s precisely because she’s a fish out of water that she’s so keenly perceptive. As another writer from the provinces, John Updike, once said of his early stint writing “Talk of the Town” pieces for The New Yorker, who else but someone from the sticks would come up with the freshest, most urbane vignettes?

So it’s a coming-of-age story as we watch Lee come to terms-or, more accurately, as she watches herself, with at least as much of the unsparing honesty she trains on her peers. At first we’re impatient with how young it all is-must we be subjected to the unchallenging observations of a freshman who believes boys have an easier time being happy than girls?-but soon enough we’re charmed by her trials. Intimidated by people with august middle names, lacking the “animal intuition” of her mates to play Madonna with the speakers facing out toward the courtyard-to be, in a word, cool-she suffers a loneliness that’s almost magical: She believes that if her woe is intense enough, it will “magnetically draw a handsome boy to her room to comfort [her].” Of course, what comforts us is our understanding that her sense of inadequacy bodes well for her future-that it’s a gift which will someday lead her to write the hard-won book we hold in our hands.

But not yet. First Lee has to work her way through that peculiar mix of distrust and disorientation that is the teenage outcast’s lot. Rarely has the purgatory of prep-school privilege been spelled out in such excruciating, subtle detail. Because she lacks the most cherished of high-school attributes-the instinct to be breezy-Lee constantly questions her place in the world. She learns that fitting in is a more complicated matter than merely laughing at jokes she doesn’t find funny (“it was an act of aggression not to”). Like an iceberg, 90 percent of her thought process is not visible to outsiders; unlike an iceberg, she’s surprisingly warm to the touch.

Which brings us to boys. Ah, boys. It goes without saying that Lee is so clueless about the opposition-teenage boys who seem predatory one minute and tender the next-that she longs for the humblest sign of acceptance, even if it’s only the “almost compliment” of having a guy call her by her last name. By her lights, she excels only at falling short, in algebra as in her love life, so that the very idea of sex leaves her “almost terrified, with hope.”

All the better, then, when sex of a sort arrives and is subjected to the same rigorous examination as everything else. Her first kiss “was harder work than I had imagined, and less immediately pleasing. In fact, it felt intriguing more than enjoyable-the shifting, overlapping wet and dry parts of our mouths and faces, the mild sourness of his mouth … and also the way it was hard not to be conscious of the moment as it happened, not to want to pause and acknowledge it, even if only by laughing. I didn’t find kissing funny, but it didn’t seem that serious, either, not as serious as we were acting like it was.”

Fast-forward to a blowjob. (Well, she does.) Surely Lee isn’t the first preppie to suggest that the discomfort of giving one confers “a sort of nobility-a kinship with all the girls who’d done this before.” But she may be the first to admit to “an affection for myself for being willing to do it.” It’s one of the reasons we come to be so fond of Lee and, by extension, Ms. Sittenfeld.

(Have I been getting the two mixed up? Blame the publisher, who made the questionable decision to send out press materials that feature photos of Ms. Sittenfeld’s real-life Groton School junior class, and even of her heartthrob-presumably the recipient of her oral largesse.)

Throughout Prep, everyday schoolgirl angst gets a makeover from the setting: The stained-glass windows of chapel lend a “tinge of nobility and glamour to even the most pedestrian kind of homesickness.” And compassion works its soft-touch magic: To win favor, Lee rather pathetically gives her classmates complimentary haircuts and finds herself acutely conscious of how “warm and vulnerable” their oblivious heads feel; she struggles all through the novel to feel for them a “true and continuous sympathy instead of mere intermittent pangs.” So it’s with regret that we wonder why Ms. Sittenfeld ultimately allows her narrator to buy into the snobbery that torments her, first by cruelly giving a potential suitor the back of her hand simply because he is “LMC” (lower middle class-part of the kitchen staff), and finally by learning to regard everyone back in South Bend with disdain (they “were fat, or wore brown ties, or seemed to be in bad moods).” Are we supposed to cheer when she’s at last achieved this level of priggishness?

In the end, Lee is liberated by graduation and the realization that the pond is a lot bigger than it’s been for the past four years. But she’s sad, too-and so are we. Perhaps it’s the knowledge that the pond is not all that much bigger, that life in the wide world is in many ways prep school writ large, and that she’ll need every one of the protective talents she’s honed-not just for the near future, but for the rest of her life, as well. In which case, may I be permitted an upperclassmen’s well-meaning word of advice? Keep the gimlet eye, kiddo, but lose the snobbery. With heart and talent like yours, it’s beneath you.

Daniel Asa Rose reviews books regularly for The Observer.