Sari Botton | Longreads | March 2015

It’s hard to believe it’s been ten years since Prep, Curtis Sittenfeld’s debut novel, was first published. And not just because the passage of time, in hindsight, is always kind of baffling, but because I have thought about that book so regularly it seems my brain only just first absorbed it.

I’d almost skipped it because I thought it was YA—which it turns out I’m more interested in at nearly fifty than I was at nearly forty, but that’s another matter. I was thrown off by the white cover illustrated with a pink and green grosgrain ribbon belt straight out of the Preppy Handbook, as well as the first lines of most reviews describing it as a “coming of age novel.”

But then it was the monthly selection for a highbrow book club I’d been somehow invited to join, a mostly Ivy-educated group with more than a few lit majors—like the woman who defended her universally rejected suggestion of choosing Dante and Milton over Zadie Smith by insisting, “We’re talking about art here, and art has its demands.” Well.

Did Prep make the cut because it takes place within a rarified ring of hell familiar to some of the book club’s members—specifically at “Ault,” the sort of elite boarding school they’d attended, and which their kids now did? Did it resonate with me to the degree it did because in a way, in that book group, I—a state school-educated underachiever from a blue collar town—was similar to Lee Fiora, Sittenfeld’s insecure teen social climber, attending Ault on scholarship as a way to escape the averageness imposed on her by growing up in a family of modest means in a Midwestern town? I’ve played that role a few other times in life, too, in exclusive spaces where I gained entrée (at least peripherally) despite a lack of a certain pedigree.

With great humor, Sittenfeld perfectly illustrates the power dynamics that play out between those with status—whether owing to race, class, gender or other factors bestowing privilege—and those seeking it, hoping to have it rub off on them. She’s most incisive about wealthy white male privilege and the confidence that comes with it. It sparks in Lee a kind of envy that she at first confuses for a crush. “The interest I felt in certain guys then confused me, because it wasn’t romantic,” she says in the narration, “but I wasn’t sure what else it might be. But now I know: I wanted to take up people’s time making jokes, to tease the dean in front of the entire school, to call him by nickname. What I wanted was to be a cocky high-school boy, so fucking sure of my place in the world.”

Lee, an awkward freshman, becomes fascinated not only with the boys at the top of the Ault Pecking order, but the girls, too. She studies all their profiles in the school catalog (at a time before Facebook), and essentially stalks them—which makes her a natural for the game of Assasin, a campus-wide contest to see who can “kill” the greatest number of fellow students by tagging them with orange stickers when they least expect it. “Undeniably,” she says, “the qualities that I usually lamented in myself—my invisibility, my watchfulness of others—now served me well.” Her studies fall to the wayside and her grades plummet as she uses her time pursuing social currency, at one point sitting under a table in the dining room for a while, waiting for her Assassin target, a popular boy from a wealthy family.

Here’s an excerpt from Prep (which totally holds up a decade after its initial release) from the chapter called “Assassin.”

* * *


Curtis Sittenfeld | Prep | 2005 | 17 minutes (4,440 words)

Gates was running roll call alone the next morning, but near the end, Henry Thorpe came and stood on the platform. Gates moved aside, and Henry stepped in front of the desk, and even though he hadn’t said a thing, people started laughing—he seemed to be imitating himself running roll call on another day. A lot of times students performed skits as announcements, and occasionally, if the senior class had a big test, they’d filibuster by performing lots and lots of skits, or making joke announcements; once, nearly twenty members of the senior class came up, one by one, to wish Dean Fletcher a happy birthday.

“So I guess that’s it for today,” Henry said. “I’ll just ring the bell now.” With exaggerated gestures, practically in slow motion, he reached to the left side of the desk where the button for the schoolwide bell was, but before he pressed it, a figure stepped forward from the fireplace near the front of the hall. The person was wearing a black robe with a black hood and carrying an oversized water gun, and when he aimed the gun at Henry, an arc of water shot over the heads of all the students sitting at the desks between the fireplace and the platform. The water hit Henry near the heart, soaking his shirt.

“Ach!” he cried. “I’m down! I’m down! They got me.” He grabbed his chest and staggered around the platform—I looked at Gates, who was standing behind Henry smiling at him like an indulgent older sister—and then Henry stepped forward and fell face-first onto the desk, his arms hanging limply in front of him.

Students cheered wildly. Not so much around me, because I sat in front with the other freshmen, and most of my classmates didn’t seem to know any better than I did what was going on. But the farther back you got in the room, the more loudly people were yelling and clapping. The person in the cloak pulled back his hood—it was Adam Rabinovitz, a senior—then threw his fists in the air. He said, or this was what I thought he said, though it was hard to hear, “Victory is mine.”

I knew three things about Adam Rabinovitz, all of which intrigued me without inspiring any desire ever to speak to him. The first was a bit of lore from two years before I’d gotten to Ault. Often at roll call people made announcements about missing notebooks or lost articles of clothing—I left a green fleece jacket in the library on Monday afternoon—and as a sophomore Adam had come up to the platform one morning, said in a completely normal voice, “Last night, Jimmy Galloway lost his virginity in the music wing, so if you find it, please return it to him,” and then stepped off the platform, while Mr. Byden glowered and students turned to each other in shock and delight. Jimmy was Adam’s roommate, a good-looking blond guy, and I wondered, though this bit of information never got included when the story was told, who the girl had been.

The second thing I knew about Adam also had, in a way, to do with sex. In the fall, a plaster-of-paris display had gone up in the art wing, a joint project by two senior girls who both wore sheer scarves around their necks and silver hoop earrings and lots of black and who probably smoked, or would start when they got to college. They were serious about their art, and that must have been why they were allowed to include in the display a variety of plaster body parts, including a breast and a penis; the breast was never identified, but after great speculation, the dominant theory on campus was that the penis belonged to Adam Rabinovitz. The third thing I knew about him, and this made the other two all the more interesting, was that supposedly he had the highest GPA in his class; at any rate, he was headed to Yale.

On the platform, Henry came back to life, and Adam joined him. “Okay, here’s the deal,” Adam said. “Assassin is starting again, and this is how we’re doing it this year. If you’re a student, we’re assuming you want to play, so if you don’t, cross your name off the class lists in the mail room by noon today. If you’re faculty, we’re assuming you don’t want to play”— here, Dean Fletcher made his own whooping cheer, eliciting laughter— “That means you do want to play, right, Fletchy?” Adam said. “Whoever gets Fletchy, remember: He’s really psyched for the game.”

People laughed more, and Adam continued. “So for you freshmen and freshwomen, I’ll give a rundown. The object of the game is, you kill all your classmates.” Again, there was laughter, laughter that makes this day and this game seem longer ago than it was; at the time, certain teachers and students expressed disapproval of Assassin, but they were viewed as the humorless minority.

“How you kill them is pretty simple,” Adam said. “The game starts at one p.m. tomorrow. Check your mailbox by twelve o’clock, and you’ll find a piece of paper with a name on it and a bunch of orange stickers. The name you get is your target, and that person won’t know that you have them. You have to kill them by putting a sticker on them without anyone seeing. If there’s a witness, you have to wait twenty-four hours before making another attempt. Once your target is dead, you take over their target, and you need to get their stickers. And don’t forget that someone else is targeting you. Any questions?”

“How many licks does it take to get to the center of a Tootsie Pop?” a girl yelled.

“It depends on your tongue,” Adam said. “Is that the best you can do?” “What’s the meaning of life?” someone else shouted.
Mr. Byden, who was standing next to Gates, tapped Henry on the shoulder, and Henry leaned in and whispered something to Adam. Adam nodded. “I’m receiving word from on high that we need to wrap up. So, basically, watch your back and trust no one. And if you have any questions, find me, Galloway, or Thorpe.” He stepped off the platform, and Henry followed him.
“You should have told them whoever wins gets the title grand master assassin,” I heard Henry say as they passed my desk. The next announcement had begun, but I was still watching the two of them.

“Or they get to blow you,” Adam said. “Whichever they choose.” They both snickered, and I smiled, as if the joke had been meant for me, too.

At that point, listening to them, I wasn’t thinking much about Assassin. What the announcement left me with mostly—I couldn’t have articulated it then, and I might not have believed it if someone else had suggested it— was the sense that I wanted to be Adam Rabinovitz. The interest I felt in certain guys then confused me, because it wasn’t romantic, but I wasn’t sure what else it might be. But now I know: I wanted to take up people’s time making jokes, to tease the dean in front of the entire school, to call him by a nickname. What I wanted was to be a cocky high-school boy, so fucking sure of my place in the world.

My first target in Assassin was Devin Billinger, a boy in my class who had, at that time, no particular significance to me. In my mailbox, I found the slip of paper with my name and his name typed on it and, attached by a paper clip, the sheet of round orange stickers. All around me, other students were finding their assignments, talking noisily. It was the beginning of sixth period, and I left the mail room to walk to the dining hall for lunch. I was just outside the stairwell leading from the basement to the first floor when, amazingly, I came face-to-face with Devin himself. Like me, he was alone. We made eye contact and did not say hi, and he turned in to the stairwell.

I was still holding the assignment sheet and the stickers. I peeled off a sticker with my index finger and thumb, keeping it affixed to my fingertip. Immediately, both my hands began to shake. I entered the stairwell. “Devin,” I said.

He stopped a few steps up and looked back. “Huh?”

Without saying anything, I closed the space between us. When we were standing on the same step, I reached out and placed the sticker on the upper part of his left arm. “You’re dead,” I said, and I bit my lip, trying not to smile.

He looked at his arm as if I’d spit on it. “What the fuck is that?”
“It’s for Assassin,” I said. “You’re my target.”
“It hasn’t started yet.”
“Yes, it has.” I held out my wrist to him, so he could read my watch: It was ten after one.
“This is bullshit.” His voice was more than irritated; possibly, though I didn’t know him well enough to be certain, he was furious. He glared at me and turned, as if to continue up the steps.

“Wait,” I said. “You have to give me your target.”
“I don’t have to do anything.”
We looked at each other, and I actually laughed. In theory, pissing off Devin Billinger should have unnerved me. He was one of a group of six or seven guys in our class known as bank boys—most of them were from New York and most of their dads had jobs having to do with investments and brokerage and other money-related matters I had no grasp of. (Technically, a bank boy didn’t have to be from New York or have a banking father—he just had to seem as if he could.) But the reality of Devin’s anger was more ridiculous than scary; he reminded me of a pouting six-year-old. “Are you planning to cheat?” I asked.

“Why are you so righteous? It’s a game.”
“And I’m just playing by the rules.”
Devin glared at me, then shook his head. He reached into his pocket, withdrew some small crumpled bits of paper, and thrust them toward me. “Here. Are you happy?”

“Yeah, I am,” I said. “Thank you.”

On Wednesday, after killing Devin, I’d killed Sage Christensen (she was a sophomore on the lacrosse team), and at dinner I’d killed Allie Wray, a senior. Both exclaimed in surprise when I tagged them, but neither seemed to care particularly. “I’m so bad at these games,” Allie said agreeably as she passed over her stickers and her target.

Yet I, apparently, had an aptitude for Assassin, and I found myself wondering—it was impossible not to wonder—if I had any shot at winning the whole game. What if I surprised everyone? What if all the boys (boys, definitely, were more into it) got so preoccupied killing each other that they forgot about me and I just stuck around, beneath the radar? Because, undeniably, the qualities that I usually lamented in myself—my invisibility, my watchfulness of others—now served me well. Maybe at the end there would come the unlikely inevitability of victory, like when I played hearts with my family and, every so often, shot the moon.

And even if I didn’t win Assassin, I still liked the extra pulse it created in the dining hall and the schoolhouse. Some people would tell you who they had, and some people were secretive—it was like grades—and supposedly a bunch of sophomores had drawn up an enormous chart, like a family tree that circled in on itself, connecting all the players. But of course, such a chart wouldn’t remain current for long, because people’s status changed hourly. I also heard that Mrs. Velle, the registrar, had given out other students’ class schedules to Mundy Keffler and Albert Shuman, who were seniors, but that after more people came by her office asking for schedules, she refused. Waiting in line for breakfast, I was told by Richie Secrest, another freshman, that at least half the student body had been killed in the first twenty-four hours. I wasn’t surprised—both Dede and Sin-Jun had been dead by the previous evening. I was toasting my bagel when I heard Aspeth say to Cross Sugarman, “If I hear another word about that goddamn game, I’ll scream.”

“Yeah, because you’re out already,” Cross said. “Don’t be a bad sport.” (In such proximity to Cross, I stared at the floor, feeling clammy and unattractive from having been outside with Conchita.)

“No,” Aspeth said. “Try because it’s lame. And because there are enough basket cases at this school as it is.”

“Sure,” Cross said. “I completely believe you.”

They were standing about three feet from me, and then their bagels fell down the slide to the front of the toaster, and they were gone. So Cross was still in, I thought, and that was when I had the idea: If I stayed alive, eventually the game would lead me to him. Or it would lead him to me, which would be even better. For Cross to be in possession of a piece of paper with my name on it, for him to travel around campus in search of me, to reach out and place a sticker on my body—the possibility made me almost sad, almost terrified, with hope. For the first time since we’d ridden in the taxi together more than a month before, we’d be forced to talk; he’d have to acknowledge me.

Life is clearest when guided by ulterior motives; walking to chapel, I felt a sense of true purpose. I was on my way to kill McGrath Mills, a junior from Dallas whom I’d inherited from Allie Wray. I’d heard McGrath was good at lacrosse, and I thought that an athlete would probably be harder to kill—there was more of a chance he’d be into the game.

I’d decided the night before that my best bet was in the rush after morning chapel. Therefore, I’d left breakfast early, without Conchita, and I found a seat in chapel near the back. Usually I sat near the front, but I knew the back was the province of drowsy junior and senior boys and of students using chapel time to finish their homework. As the seats around me filled, I kept an eye out for McGrath. At seven fifty-eight, he took a seat two rows in front of me. While Mr. Coker, a chemistry teacher, gave a talk about how he’d developed patience by observing his grandfather during boyhood fishing trips to Wisconsin, I intently watched the back of McGrath’s head.

Though you were free to leave chapel after the hymn, I usually waited until the recessional was over. On this morning, however, before the last notes of “Jerusalem” rang out, I followed McGrath toward the exit. A bottleneck had formed at the doors—this was why normally I waited—and people were pushing each other and joking around. Parker Farrell, a senior, said, “Hey, Dooley, watch your back!” and then another guy shouted, “Quit grabbing my assassin!”

Two people stood between McGrath and me, and I wormed past one, then the other. With my right hand in my pocket, I’d transferred an orange sticker from the sheet to my finger. On the threshold of the chapel, McGrath was only a few inches from me; seeing the weave of his red polo shirt up close was like seeing the pores on another person’s face.

I withdrew my hand from my pocket and placed the sticker on his lower back, and I had not taken my hand away when Max Cobey, a junior standing to my left, said, “I saw that, whatever-your-name-is freshman girl, and you’re so busted. Hey, Mills, look at your back.”

McGrath turned toward Max, and Max pointed at me.
“She just tried to kill you,” Max said.
McGrath turned around. I was looking down, blushing furiously; without raising my chin, I glanced up, and I saw that McGrath was grinning. “You?” he said.

The swarm was moving forward, and the three of us found ourselves outside, in front of the chapel.

“You’re totally busted,” Max said again, quite loudly, and he pointed down at me; he was several inches taller than I was. But he didn’t seem hostile, as Devin had; rather, he was simply enthusiastic. A few other junior guys, friends of either Max’s or McGrath’s, gathered around us.

“What’s your name?” McGrath said. He had a Southern accent, a slight twang, and he’d stuck the orange sticker from his shirt onto the pad of his middle finger.

“My name’s Lee.” 
“Did you try to kill me back there, Lee?”
 I darted glances at the faces of the other boys, then looked back at McGrath. “Kind of,” I said, and they laughed.
 “Here’s what I’m gonna tell you,” McGrath said. “It’s okay to try. But it would be wrong to succeed. You got that?”
 “Tell her,” one of the other guys said.
 “Let’s recap.” McGrath held up his right hand, the hand with the sticker. “Try, all right,” he said. He held up his left hand. “Succeed, wrong.” He shook his head. “Very, very wrong.”

“I’ll see if I can remember.”
 “Ooh,” Max said. “She’s feisty.”
 Already, I felt like I had crushes on both him and McGrath. 
“All right now, Lee,” McGrath said as he turned away. “I’ll be watchin’ you.”
“Me, too,” one of the other boys said, and he mimed like he was holding binoculars in front of his eyes. Then he smiled at me, before catching up with his friends. (Simon Thomworth Allard, Hanover, New Hampshire—that afternoon in the dorm, I studied the school catalog until I’d figured out his identity.)

I knew from the list posted outside Dean Fletcher’s office that McGrath was a server at Ms. Prosek’s table this week, and it was this knowledge that had helped me, as I’d lain awake around four o’clock in the morning, formulate a plan to kill him. Like all servers, McGrath would arrive to set the table twenty minutes before formal dinner started. When he did, I decided (and it was a decision so thrilling, an idea so perfect, that after it came to me, I did not fall asleep again before my alarm clock beeped at six-thirty), I’d be waiting beneath that table to place the sticker on his leg.

After lacrosse practice, I rushed to the dining hall and arrived by five-thirty, ten minutes before McGrath was due. Only five or six students were in the dining hall, including that night’s dining hall prefect, a senior named Oli Kehlmeier. (Being one of the three dining hall prefects was actually desirable—they oversaw the waiters at formal dinner, which meant they could boss around the younger boys and flirt with the girls.) Oli was busy spreading white cloths on the tables—it surprised me to see a dining hall prefect in fact working—and I decided to take a cloth myself from the stack near the doors to the kitchen.

I smoothed the cloth over Ms. Prosek’s table, then scanned the dining hall. No one was paying attention to me. I moved a chair out of the way, crouched, crawled under the table, and pulled the chair in. I was sitting with my heels pressed to my rear end, my knees forward, but that quickly became uncomfortable, and I switched to sitting Indian-style. There wasn’t much room to maneuver. My elbow knocked a chair, and I froze, but I heard nothing from the outside—no proclamation of poltergeist, no face appearing at the level of my own to ask what the hell I was doing— and I relaxed again. A few old-looking globs of gum were stuck to the unfinished underside of the table, I noticed, and I could smell both the table and the floor, though neither of them smelled particularly like wood; they smelled more like shoes, like not-so-dirty running shoes, or a child’s flip-flops.

At twenty of six, I tensed, anticipating McGrath. As more and more servers arrived, I felt certain that every set of approaching footsteps was his. All the tables around Ms. Prosek’s appeared occupied, and surely, I thought, they would see me, surely they’d notice the pale blue fabric of my skirt (was it gross that I was sitting on the floor in my skirt?), or see my sandaled foot. But no one approached. At the table to the right of mine, the server, I could tell by her voice, was Clara O’Hallahan, and she was singing to herself; she was singing the Jim Croce song “I Got a Name.” A little later, I heard a boy say, “Reed was in a bad mood today, huh?” and a girl said, “No worse than usual.” I waited to hear someone mention Assassin, but no one did. Eventually, the voices all became a blended, increasingly noisy hum, punctuated by the clinking of silverware and glasses. It was ten of six. McGrath wouldn’t dare miss formal dinner when he was serving, I thought, or would he? Just for skipping, you got table wipes, but if you were the server, I was pretty sure you got detention.

He arrived at four of six; well before he’d gotten to the table, I heard his cheerful drawl. Someone must have remarked on his lateness because he was saying, as he came closer, “It’s the two-minute method. Watch and learn.” Above my head, he set down what sounded like plates, then silverware. Before I could stick him, he’d left again, and he returned with a tray of glasses. His calves were mere inches from me—he was wearing khaki shorts, his leg hair was blond and thick—and he was whistling.

There were two entirely discrete feelings I had at this moment. The first was a disbelieving glee that I was really about to kill McGrath Mills. When you are accustomed to denial and failure, as maybe I was or maybe I only believed myself to be, success can feel disorienting, it can give you pause. Sometimes I found myself narrating such success, at least in my own head, in order to convince myself of its reality. And not just with major triumphs (of course whether I’d ever experienced a major triumph, apart from getting into Ault in the first place, was debatable) but with tiny ones, with anything I’d been waiting for and anticipating: I am now eating pizza, I am now getting out of the car. (And later: I am kissing this boy, he is lying on top of me.) I did this because it struck me as so hard to believe I was really getting what I wanted; it was always easier to feel the lack of the thing than the thing itself.

The second feeling I had at this moment was a sad feeling, an abrupt slackness. I think it was McGrath’s leg hair. Also, his whistling. McGrath was a person. He didn’t want to be killed, he didn’t know I was waiting underneath the table. And it seemed so unfair to catch him by surprise. I didn’t want to win the whole game, I knew suddenly. I wanted admiration, of course, schoolwide recognition, but I couldn’t possibly get through all the little moments it would require, just me and the person I was supposed to kill. With Devin, it had been okay because he’d been such a jerk, and with Sage and Allie, because it hadn’t mattered to them if they remained in the game or not. But McGrath was nice, and he seemed to care at least a little about staying alive, and yet it would have been ridiculous for me not to take him out, with the opportunity quite literally in front of me. And it wasn’t even that I entirely didn’t want to. It was just that it seemed complicated. From now on, I thought, I’d do whatever was necessary to get to Cross. But I wouldn’t be zealous, I wouldn’t think the game itself actually mattered. This was the decision I was making as I extended my arm and placed the sticker on McGrath’s calf—I placed it just to the side of his tibia bone, almost exactly halfway between his ankle and knee. Then I pushed out the chair in front of me and emerged from beneath the table on my hands and knees. Looking up at McGrath from that position, I couldn’t help feeling a little like a dog.

His expression, as I’d feared, was one of naked surprise. I am not even sure he recognized me immediately. I stood, and said, uncertainly, “I just killed you,” and though McGrath broke out laughing, I think it was only because he was a good sport.

“Oh, boy,” he said in his Southern accent. “You nailed me. Man, did you get me good. How long were you under there?”

I shrugged.

“That’s a well-deserved win. Hey, Coles, look who was under my table. I know, she was stakin’ me out!” McGrath turned back to me.

“Sorry,” I said.

“Don’t be sorry. What are you sorry for? You got me fair and square. I gotta give you my stickers, right? But you know what?” He felt in the back pocket of his shorts, and in the pockets on both sides of his blazer. “I left ’em in my room,” he said. “Can I give ’em to you later? I’ll come up to your dorm and do a hand-delivery.”

“That’s fine,” I said. “Anything’s fine.” (Of course he didn’t have his stickers. The game didn’t really matter to him.)

I knew right away that I had ruined it. Whatever jokiness had existed between us—I had killed the substance of it. McGrath would be friendly to me from now on (and I was right in thinking that, he always was friendly, for the year-plus that remained before he graduated from Ault) but the friendliness would be hollow. In killing him, I had ended the only overlap between our lives. “Assassinate anyone lately?” he would ask, months later, when we passed each other, just the two of us in a corridor of the third floor between fifth and sixth periods. Or, “How are your pillowcases holdin’ up?” I might laugh, or say, “They’re okay”—something short. McGrath didn’t want to talk, of course, it wasn’t as if we had anything to say to each other. I knew all this, I understood the rules, but still, nothing broke my heart like the slow death of a shared joke that had once seemed genuinely funny.

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From the book PREP by Curtis Sittenfeld. Copyright © 2005 by Curtis Sittenfeld. Reprinted by arrangement with Random House, an imprint of Random House, a division of Penguin Random House LLC. All rights reserved.