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Choosing the Right (Fictional) Prep School

July 16, 2009 by Reader's Connection

When I told Tom Short at Central Library that I was doing a blog posting about prep school novels, he said I should throw in some classics–including A Portrait of the Artist as a Young Man by James Joyce. My wife asked if I was going to include the Harry Potter books. I’ve decided to limit the posting to fiction about prep schools in the United States.

Old School by Tobias Wolff

Old SchoolWolff’s 2003 novel inspired this list. The author attended a prep school, himself, and like the unnamed narrator of his tale, he had to leave without completing his studies–though his reasons for departure weren’t as weird as the narrator’s.

“There was a tradition at my school,” the narrator tells us, “by which one boy was granted a private audience with each visiting writer.” The boys compete for this privilege by writing poems or stories of their own, and the competition is ferocious. The visiting writers–Robert Frost, Ayn Rand and Ernest Hemingway–make the final selections, and each of these celebrated authors makes a questionable choice.

There’s a great deal of humor in this story of young men fumbling toward their identities. Ayn Rand’s visit is funnier than any movie you’ll see this summer; and after paying serious homage to Hemingway, Old School slyly turns around and kicks him in the butt.


Here are two novels by Louis Auchincloss, a master chronicler of East Coast wealth. If you want the full experience of prep school fiction, you can’t skip The Rector of Justin (1964).
The Rector of Justin

World War II is erupting overseas. Dr. Francis Prescott is the founder and headmaster of Justin Martyr, an Episcopal boys’ school west of Boston; and Brian Aspinwall, a student at Justin, finds himself unofficially assigned to write Prescott’s biography. Brian receives fragments of narrative from various characters, and the portrait that emerges is compelling. You really haven’t been to prep school (novelistically speaking) until you learn how the building of the chapel was funded.

When I first read the book, thirty-some years ago, Brian drove me crazy, as did Horace Havistock, who contributes the first piece of “Prescottiana.” But I didn’t have to struggle with these narrators while rereading the novel. Brian fully engaged me. Either my range of sympathies has grown, or I’ve become a fusspot, myself, and don’t object to the company of others.


The Headmaster´s Dilemma

The Headmaster´s Dilemma (2007) is a shorter, sleeker novel. Auchincloss looks into the past, again–the past in this case being 1975.

Michael Sayre is the headmaster of Averhill, another New England boarding school. When one boy accuses another of rape, Michael’s enemies do their best to play politics with the incident. The story moves among different points of view, and I should mention in passing that the wives of headmasters–in both Auchincloss books and some of the others, here–weave surprising threads into their sagas.







The Finishing School by Michele Martinez (no longer in our collection as of 3/2015)

The Finishing School

Does  this qualify as a prep school novel when the main character, federal prosecutor Melanie Vargas, only visits the school on a need-to basis while investigating the deaths of a couple of students?

Sure it does. I wanted to include at least one novel featuring a preparatory school for girls rather than boys; and of all the novels on this list, The Finishing School is the one with the least complicated message: DO NOT enroll your daughters at Miss Holbrooke’s School in Manhattan .

Ms. Vargas’s love life bores me, but her visit with her estranged father in Puerto Rico  is well done, the deaths are chilling, and the crime plots wrap around each other nicely. Good suspense.






A Separate Peace by John Knowles

A Separate Peace

Talk about a prep school classic. I somehow made it through adolescence without reading this one–teenagers didn’t know about it, yet, at least not in Merrillville–and waiting until I was senile may have been a mistake. These characters don’t come alive for me.

I’m all for downbeat fiction that explores our human darkness (“some ignorance inside me, some crazy thing inside me, something blind,” as the narrator Gene describes it), but Gene’s roommate Phineas is a big stuffed animal with athletic abilities, and Gene is a bore who writes shapely sentences.

The fact that the novel may have “a gay subtext” is no help. I’m borrowing that phrase from Wikipedia, and there are disagreements at that site. (“Would the person who keeps deleting my references to homosexuality please justify said deletions? My inclusions are factual and relevant.”) Maybe some of our books of criticism about John Knowles clear all this up. I don’t care. The book is inert.

Remember, though, it’s a classic. I’m probably wrong.

The Headmaster’s Wife by Jane Haddam (no longer in our collection as of 3/2015)

The Headmaster's Wife

The Windsor Academy is just outside Boston–as is Auchincloss’s Justin Martyr. The administration likes to talk about the school’s “diversity,” but in the end everything is decided by money. Yes, this is another school to avoid–people are getting bumped off–but don’t avoid the book. The coming of the Bouchercon World Mystery Convention to Indianapolis has me cranked up about mysteries, again, and I want to read more about Haddam’s Gregor Demarkian.

The musings of some detectives are a drag. Travis McGee’s pontifications from his houseboat always annoyed me. But I could read Demarkian’s musings all afternoon.

If there was some explanation for why people did what they did, some reason that fit the greater purposes of the cosmos, why some men could only reach orgasm if the woman they were with was soon to be a corpse, Gregor didn’t know what it was. He’d never understood murder on any level. Even the obvious murders–the woman . . . who was killing her husbands for their insurance, racking up the cash, playing at killing the way high-stakes gamblers played at casinos–seemed to him overdone, overfelt, overemoted. Maybe the truth of it was that murders were committed by people who took themselves too seriously, by people who could not see into the future and understand that life would end for everybody, even for them, and that the things in it were not as important as that fact.



Haddam and Martinez set their crime stories in the present day. Wolff and Auchincloss and Knowles all look into the past. Dave Kalstein’s Prodigy transpires in the future. I find this innovation upsetting, and haven’t been able to read the book. Prodigy

This genre-blending mix of science fiction, thriller, and bildungsroman begins in 2036 with the murder of one of Stansbury School’s very few ne’er-do-well alumni. Stansbury doesn’t have a lot of failures because it churns out prodigies: the school’s “med cycle” makes kids big, strong, brilliant, and hard-working learning machines. (It also makes the girls big breasted, as is mentioned several dozen times.) Stansbury’s grads have already cured AIDS and cancer, invented flying machines (natch), and been elected to the U.S. Senate. In fact, the Senate is considering a $1 trillion grant to Stansbury. But then the school’s valedictorian starts asking questions about alumni murders. He joins up with a drugged-out, bottom-of-the-class kid named Cooney, and together they race to unravel the plot. Engrossing despite its well-trod utopia-gone-bad plot, the book is so well imagined that one cares about the school’s fate from the start. And the characters are vivid as well, befitting what is, beneath its fast-paced surface, a thoughtful novel about boarding-school life. — Booklist


Things to remember:

1) Aside from The Finishing School, all these novels describe life at boarding schools. Most prep schools in the real world aren’t boarding schools–the students go home at night–but boarding schools make for interesting fiction.

2) It may be true that well-educated Easterners don’t all talk the way characters talk in Louis Auchincloss novels. Don’t worry about it. “I am sure that not even the most civilized of these Wall Street types is given to quoting King Lear and Saint-Simon quite as often as their author has them do.” Gore Vidal wrote that, in a wonderful essay about Auchincloss in The New York Review of Books. But that complaint is a minor touch in what is really a pro-Auchincloss rave, available in a bound volume at Central Library (July 18, 1974 –Vol. 21, Number 12) or on the NYRB website, if you want to spend the three dollars. (And maybe it’s gone from there – 3/2015)

3) Do not enroll your daughters at Miss Holbrooke’s School in Manhattan.


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