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Prep

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August 28, 2018 at 12:00 PM EDT

Nora Ephron says it best: The end of summer evokes a pang for back-to-school, and all that it entails, like nothing else. Even if you’re not school-supply-shopping in New York or sending your crush a bouquet of freshly-sharpened pencils, the crisp fall air just does something to a person. For the book lovers among us, we feel drawn to campus novels to get lost in the world of textbooks, messenger bags, and fictional boarding school romances. Almost no tome evokes this seasonal spirit better than Curtis Sittenfeld’s Prep.

Sittenfeld’s coming-of-age novel about the intrepid Lee Fiora, who is thrust into the blazer-filled world of the prestigious Ault School, is a cult classic like no other. For the last 13 years readers have been drawn to its pointedly honest (and often times biting) commentary on the world of elite New England private schools. That, year after year, it is equally passed around real-life boarding schools as a self-indulgent celebration of their own lives (remember when the cast of Laguna Beach used to watch The O.C.?) and passed among young women who found the moneyed world of trust fund babies fascinating and horrifying, is a prime example of the book’s broad appeal.

Perhaps the most impressive piece of trivia about Prep is that it was Sittenfeld’s debut novel. She spoke with EW to share the story about her still-famous novel from over a decade ago, and it all began at the Iowa Writer’s Workshop, where the author was working on her degree. As part of an assignment, she wrote what would later become the last chapter of Prep — but had no intention of turning it into a full-length book at the time.

“I graduated from Iowa in May 2001, and I felt like I had this sort of moment of truth with myself,” explained Sittenfeld. “Where I’d thought, you know if I really want to be a writer I have to finish a book. And I asked myself what do I have, and how do I get to the end of it?”

Sittenfeld was 24 years old when she got to work on the book — and 29 when it published. She took the finished product to her agent, Shana Kelly, who submitted the manuscript to 15 different editors. In a scenario that has come to be all-too-familiar to aspiring authors, several publishing companies expressed interest but then ultimately backed out — some of then even did so several times in a row, until Random House decided to bite.

“People always say to me, how did you decide which publisher to go to,” laughed Sittenfeld. “And I would say it really wasn’t that difficult.”

In spite of the difficult road to publication, Prep took off as soon as it hit shelves. It became a near-instant bestseller and immediately begat not only fervent gushing among teens and adults alike, but a debate about the real-life inspiration for the fictional (or was it?) school and students featured in the novel. Sittenfeld herself not only attended the prestigious Groton School but was serving as a writer-in-residence at the all-boys St. Albans School at the time she finished the book, which provided plenty of inspiration.

“The setting [of Prep] is essentially Groton,” she said. “The layout of the campus, the schedule of the day, the ritual of the school, those are things I liberally borrowed from Groton.”

The author is quick to point out that almost none of the characters are based on real people from her time at boarding school, including the protagonist Lee. (She did let slip that many of the students’ absurdist names are borrowed from or inspired by WASP-y naming practices). But a few moments from her time at St. Albans made their way onto the page.

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“There is a reference to an editorial in the student newspaper that I think literally ripped off a St. Albans editorial about how students should be allowed to wear plaid shorts to class or something like that,” said Sittenfeld. “It was just so irresistibly preposterous that I couldn’t help myself.”

The novelist also borrowed from real life for the book’s central plot device: The infamous game “Assassin,” which pits Lee against her fellow Ault co-eds to see who can tag more people with the foreboding orange stickers, was played during Sittenfeld’s time at Groton. She believes it’s still played there to this day, and yes, that Gossip Girl episode was indeed inspired by the game from Prep.

Some of the book’s other iconic moments almost didn’t come to be — like the title, for starters, which was initially meant to be Cipher but was changed by Sittenfeld’s editor out of concern readers wouldn’t know what the word meant. And the instantly-recognizable cover began as an image of an ivy-covered fence, intended to evoke academic exclusivity. Sittenfeld was reading O Magazine and found a blurb about green ribbon belts making a fashionable comeback; the headline declared “Get Prepped,” so she sent it over to her editor to share the word-play sighting.

“Her assistant emailed me and said, we really like the idea you sent, and we’re working on it, and we’ll have something to show you soon,” the author explained. “It was literally based on a misunderstanding, but then immediately when I saw the new cover, I thought, ‘Oh my God, that’s great.’”

Now, 13 years after that green-ribbon-cover first hit shelves, Sittenfeld is a prominent author. She published her sixth book this spring, a short story collection that has since been optioned by Reese Witherspoon’s Hello Sunshine, a position which gives her a wholly different perspective when it comes to reminiscing on her fairytale debut.

“When I look back, I feel as if my experience with Prep was sort of every first novelist’s delusional idea of how their book will be received,” she laughed. “I also didn’t understand that it’s very unusual for a debut novel that received a $40,000 advance to become a bestseller. It’s shockingly unusual — this was never supposed to be a bestseller.”

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