The It Girl


By Cecily von Ziegesar

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Popular Gossip Girl character Jenny Humphrey is leaving Constance Billard to attend Waverly Academy, an elite boarding school in New York horse country where glamorous rich kids don’t let the rules get in the way of an excellent time.

Determined to leave her Manhattan past behind her, Jenny sets off to Waverly with big plans of reinventing herself. She’ll be a goddess–she’s a sophisticated city girl, after all!–and will find a boy who can properly worship her. But that’s going to be a little tricky since her self-absorbed new roommates, Callie Vernon and Brett Messerschmidt, aren’t exactly there to help–unless there’s something in it for them.

Hot guys, new intrigue, and more delicious gossip all add up to more trouble than ever for Jenny. But if getting caught with boys and going up against the Disciplinary Committee is what it takes, Jenny’s ready. She’ll do all that and more to be The It Girl.


Copyright © 2005 by Alloy Entertainment

All rights reserved. Except as permitted under the U.S. Copyright Act of 1976, no part of this publication may be reproduced, distributed,or transmitted in any form or by any means, or stored in a database orretrieval system, without the prior written permission of the publisher.

Little, Brown and Company

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First eBook Edition: November 2005

ISBN: 978-0-316-04197-3

The characters and events portrayed in this book are fictitious. Any similarity to real persons, living or dead, is coincidental and not intended by the author.



Somebody's plaid Jack Spade duffel slammed into Jenny Humphrey's shin and jerked her out of a dream. The 10 A.M. Amtrak Empire Service to Rhinecliff, New York, had stopped in Poughkeepsie, and a tall, twentyish, stubbly chinned boy in dark brown square Paul Smith glasses and a Decemberists T-shirt was standing over her.

"Anybody sitting here?" he asked.

"Nope," she responded groggily, scooting over. He threw his bag under the seat and settled in next to Jenny.

The train groaned along at about a mile an hour. Jenny sniffed at the stale, slightly sweaty train car air and jiggled her foot, thinking about how she was going to be super-late for check-in at Waverly Academy. She would've been early if her dad, Rufus, had driven her up here in his blue beater Volvo wagon—he'd practically begged Jenny to let him—but Jenny hadn't wanted her unshaven, peacenik father to drop her off at her brand-new, haute boarding school. Knowing him, he'd have tried to start up an impromptu poetry slam with her new classmates and shown off old pictures of Jenny when she was a lame seventh grader and wore nothing but fluorescent green and orange Old Navy fleeces. Um, no thanks.

"Going to Waverly?" the boy asked. He raised his eyebrows at the Waverly Academy Guide to Ethics that sat unopened in Jenny's lap.

Jenny brushed a brown tendril out of her eyes. "Yeah," she answered. "I'm starting there this year." She couldn't hide the enthusiasm in her voice—she was so excited to start her brand-new boarding school that she felt all jiggly inside, like she had to pee.


"Nope. Sophomore. I used to go to Constance Billard. It's in the city." Jenny was a little pleased that she had a relatively chic past to refer to, or that it at least sounded that way.

"So you wanted a change of pace, or what?" He fiddled with the strap of his worn leather watchband.

Jenny shrugged. This boy looked like he was her brother Dan's age. Dan had just taken off for Evergreen College on the West Coast two days ago, taking nothing with him except for two duffel bags, his Mac G4 laptop, and two cartons of cigarettes. Jenny, on the other hand, had already shipped four over-size boxes and a couple of giant duffels to Waverly, and had lugged a giant suitcase and an overstuffed bag with her. In her hyperexcited preparation for boarding school, she had practically bought out the hair, cosmetics, and feminine products aisles at CVS—who knew what she'd need at boarding school! She'd also gone on a buying spree at Club Monaco, J.Crew, and Barneys with the credit card her dad had lent her for back-to-school shopping. "Kinda," she finally answered.

The truth was, she'd been asked to leave Constance—apparently because she was considered a "bad influence" on the other girls. Jenny hadn't thought she was being a bad influence at all—she was just trying to have fun, like every other girl at school. But somehow, all of her moments of extreme fun had also been highly publicized and embarrassing: a picture of her boobs in a sports bra had shown up in a magazine (she'd thought it was a sportswear model shoot), a Webcast of her practically naked butt had been spread around the school, and she'd made some bad decisions about which boys she should make out with at various parties—and of course everybody had found out.

The final straw had come after Jenny had spent a night at the Plaza Hotel with her brother's old band, the Raves. A photograph of her leaving the Plaza in nothing but a fluffy white bathrobe had appeared online on Page Six the next day. Rumors had flown that Jenny was sleeping with all the Raves, including her brother. Ew! Concerned parents quickly called up the Constance headmistress, aflutter about Jenny's promiscuity. After all, Constance had a reputation for excellence to uphold!

Although Jenny hadn't even been with one Rave, let alone all of them, she hadn't exactly wanted to deny the rumor—she kind of loved that everyone was talking about her. So as she'd sat with the Constance Billard headmistress, Ms. McLean, in her patriotic red, white, and blue office back in the city, Jenny had realized something huge: it wasn't the end of the world to get kicked out of Constance. This was her chance to start over, to reinvent herself as the blunder-free sophisticate she'd always wanted to be. And where was the classiest place to start over? Boarding school, of course.

Much to her dad's chagrin—she was pretty sure Rufus wanted her to live with him in their Upper West Side apartment forever—Jenny had rabidly researched a whole bunch of schools and toured a few. The first school had turned out to have a strict disciplinary code and had been too boring for words. Within minutes of getting to the second school, on the other hand, she'd been offered Ecstasy and had taken her top off. But just like the third bed for Goldilocks, the third school that Jenny had tested, Waverly, was just right.

Well, to tell the truth, she hadn't actually visited Waverly—she'd run out of time, applied way past the deadline, and taken some creative liberties with her application—but she'd looked at thousands of pictures online and memorized all the building names and campus maps. She was certain it would be perfect.

"I used to go to Waverly's rival," the boy said, pulling a book out of his bag. "St. Lucius. Our school hated your school."

"Oh," Jenny replied quietly, sinking into her seat.

"I'm kidding." He smiled and turned back to his book. Jenny noticed it was Henry Miller's Tropic of Cancer, one of her dad's favorites. According to Rufus, it had been banned because it was too right on in its vicious social commentary about love and sex in New York City. Hello, sex scenes. Jenny felt her cheeks growing pink.

Then she realized: she was acting like her old, unsophisticated self. And one thing was for sure: Old Jenny obviously wasn't working for her.

Jenny studied the boy carefully. She didn't know him and would probably never see him again, so why did she care what he thought of her? At Waverly, Jenny was going to be stunning, amazing New Jenny, the girl who belonged at the center of everything.

So why not become New Jenny starting right now?

Mustering up her courage, she uncrossed her arms to reveal her rather large double-D chest, which seemed even bigger, since she was barely five feet tall, and sat up straight. "So, um, any good parts in that book?"

The boy looked puzzled, his eyes darting back and forth from Jenny's innocent face to her chest to the worn paperback's cover. Finally, he wrinkled his nose and answered, "Maybe."

"Will you read some to me?"

The boy licked his lips. "Okay. But only if you read me a line from that book you've got there first." He tapped the maroon cover of her beloved Waverly Academy Guide to Ethics.

"Sure." Jenny opened the rule book. She'd received it a few weeks ago and had devoured it cover to cover. She loved its plush leather binding, its creamy paper stock, and the nursery-rhymey, slightly condescending, slightly British style in which it was written. It sounded so wonderfully proper and upscale, and Jenny was sure that by the time she'd even spent a few weeks at Waverly, she'd be as polished, graceful, and perfect as Amanda Hearst, the young socialite, or the late Carolyn Bessette Kennedy.

She cleared her throat. "Here's a good one. 'Waverly Owls may not dance in a sexually suggestive manner in public.'" She laughed. Did that mean they could dance in a sexually suggestive manner in private?

"Do they really refer to you as Waverly Owls?" The boy leaned over to look at the page. He smelled like Ivory soap.

"Yes!" As she said it, Jenny grinned. She, Jenny Humphrey, was going to be a Waverly Owl!

She turned the page. "'Waverly Owls are not permitted sexual intimacy. A Waverly Owl must not engage in activities that might be dangerous, such as jumping off the Richards Bridge. A Waverly Owl does not wear spaghetti straps or miniskirts above midthigh.'"

The boy snickered. "When they're talking about a girl, shouldn't it be an Owlette?"

Jenny slammed the book shut. "Okay. Now it's your turn."

"Well, I just started, so I'll read from the beginning." The boy smirked and opened to the first page. "'From the very beginning, I have trained myself not to want anything too badly.'"

Funny, Jenny thought. She had the opposite problem—she wanted everything way too badly.

"'I was corrupt,'" he continued. "'Corrupt from the start.'"

"I'm corrupt!" Jenny blurted out. "But not from the start." Old Jenny couldn't believe what New Jenny was saying.

"Yeah?" He closed the book. "I'm Sam, by the way."

"Jenny." She looked down to see if Sam wanted her to shake his hand, but it was still wedged under his leg. They both smiled awkwardly.

"So, does your corruptness have anything to do with why you're leaving New York for boarding school?" Sam asked.

"Maybe." Jenny shrugged, trying to be coy and mysterious at the same time.


She let out a sigh. She could admit the truth, but Everybody thought I was sleeping with all the guys in this band, and I didn't deny it sounded kind of slutty. Definitely not mysterious or chic. So instead she decided to take some creative liberties. "Well, I was in a sort of risqué fashion show."

Sam's eyes glittered with interest. "What do you mean?"

She thought for a moment. "Well, for one look, I just had this bra-and-underwear set on. And heels. I guess it was a little too much for some people."

This wasn't entirely a lie. Jenny had modeled last year—for a Les Best spread in W magazine. Clothed. But clothes didn't seem too interesting at the moment.

"Really?" Sam cleared his throat and readjusted his glasses. "Have you heard of Tinsley Carmichael? You should know her."


"Tinsley Carmichael. She goes to Waverly. I go to Bard now, but I met her a couple times at parties last year. . . . She came to school in her own seaplane. But someone told me she decided to leave Waverly because Wes Anderson offered her the lead in his next movie."

Jenny shrugged, feeling strangely competitive with—and a wee bit excited about—this Tinsley girl. She sounded like the ideal New Jenny.

The exhausted-looking train conductor stomped down the aisle and grabbed the ticket off the top of her seat. "Rhinecliff, next."

"Oh. This is me." Jenny took a deep breath. It was really happening! She looked out the window, expecting to see something truly magical, but saw only lush green trees, a wide field, and telephone poles. Still, trees! A field! The only field in Manhattan was Sheep Meadow in Central Park, and it was always filled with drug dealers and really skinny half-naked girls sunbathing.

She stood and reached for her red and white polka-dotted soft-shell LeSportsac bag and the old-school brown Samsonite suitcase she'd borrowed from her dad. It had a big HUGS NOT BOMBS sticker next to the handles. Not very New Jenny. As she struggled to bring the case to the ground, Sam stood to help her, pulling it effortlessly off the rack.

"Thanks," she said, blushing.

"No problem." He pushed the hair out of his eyes. "So, do I get to see pictures of you at . . . at the fashion show?"

"If you search online," Jenny lied. She stared out the window and saw, across a field, an old rooster weathervane on the top of a large, faded farmhouse. "The designer's name is, um, Rooster."

"Never heard of him."

"He's kind of obscure," Jenny answered quickly, noting that the polished, pink Polo wearing boy sitting behind them was definitely listening to their conversation. Jenny tried to see what he was typing on his BlackBerry, but he covered the screen when he noticed her watching him.

"You . . . you should come to Bard sometime," Sam continued. "We have some killer parties. Great DJs and stuff."

"Okay," Jenny replied over her shoulder, raising her eye-brows just a touch. "Although, you know, a Waverly Owl isn't allowed to dance in a sexually suggestive manner."

"I won't tell on you," he answered, not taking his eyes off her chest.

"'Bye, Sam," Jenny waved, using her most flirty, musical voice. She stepped off the train onto the platform and sucked in a deep breath of fresh country air. Whoa.

New Jenny would take a little getting used to!

RyanReynolds: Hey, Benster. Welcome back, girl!

BennyCunningham: Hey, sweetie! How's life?

RyanReynolds: I had the worst ride up here in our plane. My dad has this maniac pilot and they were yakking at each other the whole time and going faster and faster. . . .

BennyCunningham: Next time you should fly with me. I'll let you snuggle with me under my pashmina.

RyanReynolds: God, you're a tease. Hey, did u c Callie's pic in Atlanta Magazine?

BennyCunningham: No, but I heard it nearly ruined her mom. She had to do damage control on Good Morning Atlanta!

RyanReynolds: Yeah, C looks bombed in the pic.

BennyCunningham: Is she still with EZ? I'm going to jump him if she's not.

RyanReynolds: Dunno. Someone told me they saw him dancing with some gorgeous girl with really blue eyes and black dreads in Lexington.

BennyCunningham: Sorta sounds like Tinsley. Except for the dreads.

RyanReynolds: I know. Too bad she won't be at the party tonight.

BennyCunningham: Seriously.



Callie Vernon set her luggage down in the entranceway to Dumbarton dorm room 303 and looked around. The room was exactly as she, Brett, and Tinsley had left it—except for the lack of empty Diet Coke bottles, Parliament butt–filled ashtrays, and CD cases strewn all over the room. Last fall, because they'd only been sophomores, Callie and her two best friends, Brett Messerschmidt and Tinsley Carmichael, had been assigned a horrible, cramped room with only one window. But then Tinsley had bribed three dorky senior girls to switch with them the first week of school by promising them invites to the best secret parties. They'd wanted this room because it was bigger than most, with casement windows over-looking the Hudson River, and because it was close to the fire escape—ideal for sneaking out after curfew.

Brett hadn't arrived back at school yet, and Tinsley had been expelled at the end of school last year. They'd been caught on Ecstasy in the middle of the rugby fields at five in the morning by Mr. Purcell, the uptight physics teacher, who liked going running with his three impeccably groomed giant schnauzers before sunrise. It was the first time they'd ever tried E, and it had taken them a moment to stop laughing at the ridiculous-looking dogs before realizing what enormous trouble they were in. The girls had all been called into the head-master's office separately—first Tinsley, then Callie, then Brett—but the only one to get in any real trouble was Tinsley, who was promptly booted out of Waverly.

Callie caught a glimpse of herself in the just-Windexed mirror over the antique oak bureau and straightened her white Jill Stuart shell top and pleated lemon-yellow Tocca skirt. She'd lost a few pounds over the summer and the side zipper kept sliding around to her belly button. Callie was thin now, maybe a little too thin, and freckly from the summer. Her hair was long and shaggy, and her round, hazel eyes were fanned by thick, blond-tipped eyelashes. She puckered her lips, blew a kiss at the mirror, and felt an anxious flutter in her chest.

All this summer, Callie's mind had spun, thinking about why Tinsley had been expelled and she and Brett hadn't been. Had Brett set it up that way? Brett was supersecretive about her life at home—her mom and dad never came to Parents' Day, and Brett never invited anybody to her house in East Hampton for long weekends. Tinsley had once dropped a hint that Brett had some family issues she didn't want anybody to know about. Could Brett really have orchestrated Tinsley's expulsion so she wouldn't expose her secrets? It sounded totally soap-operaish, but Brett was so melodramatic sometimes that Callie wouldn't put it past her.

Callie nestled into her desk chair, actually glad to be back at school. Beyond not talking to her two best friends—she hadn't heard a peep from either of them—her summer had been a disaster. First, there'd been the Atlanta Magazine photo of Callie at Club Compound, dancing on a table with a vanilla martini in her hand. The caption read, Overserved and underage: Is this appropriate behavior for a governor's daughter? Needless to say, that hadn't gone over well with her mother's conservative Georgian voters. Oops.

After that nightmare, Callie had flown to her family's chalet in Barcelona—Mr. Vernon was part Spanish and spent his summers working on real estate deals in Europe. She had hoped that Barcelona would be the perfect backdrop for a romantic rendezvous with her boyfriend, Easy Walsh. But that visit had been anything but romantic. Try freaky.

"Hey," came a gravelly voice behind her.

Callie wheeled around. Easy. There he was, all rumpled, sexy six feet of him, standing in her doorway, looking more gorgeous than ever.

"Oh!" She felt her palms get slick with sweat.

"How are you?" he asked, pulling at the worn hem of his polo shirt. His glossy almost-black hair curled around his neck and ears.

"Confused" would have been a reasonable answer. The last time she'd seen Easy was when she'd dropped him off at the Barcelona airport. They hadn't kissed goodbye, and they'd barely even spoken the whole last day of his visit.

"Fine," she replied cautiously. "How did you get in here? Did Angelica see you?" Her dorm mistress, Angelica Pardee, was really strict about allowing boys in the all-girls' dorm except during "visitation," which was only for an hour between sports practice and dinner.

"You look too skinny," Easy said softly, ignoring Callie's questions.

Callie frowned. "Do you want to get in trouble on the first day of school?"

"Your boobs are going away," he continued.

"God," she muttered in annoyance. The truth was, she hadn't been hungry all summer—not even for Barcelona-style paella, her favorite. She was too nervous to eat, or to do much of anything, really. The last few weeks in Spain she'd spent on the couch, looking like an unstructured slob, wearing her slightly ragged, white Dior string bikini and some old ripped batik sarong she'd picked up for next to nothing in a Barcelona out-door market, watching hours and hours of The Surreal Life in Spanish. And she didn't even speak much Spanish. "What are you doing back so soon?"

Easy was usually fashionably late to Waverly check-in—another no-no—because he arrived in a tractor-trailer with his Thoroughbred, Credo, who he kept on campus.

"Credo's coming next week, so there was no reason for me to be late."

He looked at Callie. They'd been together since last fall, but he'd had a hard time getting psyched to see her back at school after his parents had received an angry note from Dean Marymount over the summer saying he'd be watching Easy carefully this year. Apparently there were rules to uphold, and just because Easy was a legacy—his grandfather, father, and three older brothers had all attended Waverly—didn't mean he could bend those rules. So instead of heading up to school a week late with Credo, Easy had flown alone on a chartered plane from Kentucky to New York with leather reclining seats and unlimited champagne. Sounds great, right? Except it wasn't exactly what Easy had had in mind.

Easy regularly fantasized about getting kicked out of Waverly Academy—until he remembered his father's bargain. If Easy graduated from Waverly, he could take a postgraduate year in Paris. His father even had a big apartment in the Latin Quarter all ready for Easy's year abroad. Paris—how cool would that be? He'd drink absinthe, paint street scenes from his bedroom window, and ride along the Seine on an ancient, rickety Peugeot bike, a Gauloise hanging from his mouth. He could smoke his brains out and nobody would give him shit for it!

"You going to the party at Richards' lounge tonight?" Callie asked.

Easy shrugged. "Not sure." He stood just inside the door frame.

Callie pulled a foot out of her pointy-toed Burberry loafer and rolled her ballerina-pink painted toes against the floor. A horrible feeling of dread washed over her. Why wouldn't Easy want to go to the first party of the year? Everybody went to the first party of the year. Was he seeing someone else? Someone he wanted to be alone with on the first night of school?

"Well, I'm going," she said quickly, crossing her arms.

Neither one had made a move toward the other. But with his mussed hair, broad shoulders, and golden-brown forearms, Easy looked so irresistible, Callie was dying to lick him from head to toe.

"Did you have a good summer after Spain?" she squeaked, trying to sound as indifferent as possible.

"I guess. Lexington was ass-boring as usual." He pulled a toothpick from behind his ear and placed it between his slightly chapped lips.

Callie leaned against her antique white-painted wood bed frame. His visit to Spain had been tainted from the start. Easy had had to fly coach class, and when he'd arrived, he'd been terse and gruff and had headed straight to the bar—not one of those cute little outdoor cafés straight out of The Sun Also Rises, but simply the closest bar possible, at the airport. Then he'd passed out on the Vernons' couch, which was a real problem since Callie's dad needed to sit on that couch to watch the international feed of CNN every single minute he wasn't working.

Callie tilted her hips forward and chewed on her freshly manicured thumbnail. "Well, that's nice," she responded finally. She wished she could just wrap her arms around him and kiss him everywhere, but she couldn't exactly do that when he hadn't even tried to hug her hello.

Then she spied a familiar figure behind Easy and her heart started racing.

"Mr. Walsh!" crowed Angelica Pardee, Dumbarton's dorm mistress. Angelica wasn't even thirty, but she seemed to be in a hurry to enter middle age. Today she was wearing a thin, shapeless tan cardigan, a straight, knee-length black skirt, and sensible black Easy Spirits. Her calves were a little veiny and way too bluish-white, and she wore no makeup. "Do I have to report you already?"

Easy jumped. "I'm sorry," he apologized, dazedly pressing his hand to his head, as if he had amnesia. "I haven't been here in so long, and, like, I forgot which dorm I was in." He looked across the room, directly into Callie's eyes, and she felt her arms goose-bump.

"See you later?" she finally mouthed.

He nodded ever so slightly.

"Stables?" she whispered.

"Tomorrow?" he mouthed back.

"Why not tonight?" Callie wanted to ask. But she didn't.

"Mr. Walsh!" Angelica practically spat, gripping the cuff of his shirt. Her face was an abnormal red.

"Okay!" Easy yelped. "I said I was leaving."

Angelica shook her head and ushered Easy down the hall.

Callie turned and stared out the window. The abandoned stables were where they used to go last year to fool around. Only a few students kept horses at school, so several of the stalls were always empty. She hated that she had had to suggest they meet there, and not the other way around.

Droves of freshmen lumbered up Dumbarton's steps, carrying way too much luggage. Callie noticed how overwhelmed the girls seemed. She could relate. There were so many things about boarding school that you couldn't plan for. They'd soon discover that they didn't need half their shit and that they had forgotten the really important stuff—like empty shampoo bottles to hide vodka in. She watched the throng of freshman girls part as Easy strolled down the Dumbarton steps, nodding to the new, innocent faces. God, it was hard dating such a flirt.

She put her head in her hands. It was so obvious what had gone wrong in Spain. The last night they'd spent together, she'd admitted something to Easy that was so big and so scary for her to say. And what had been his answer? Nothing. Silence.

Callie sighed. They'd have to talk about it tomorrow, although she hoped they'd be doing a lot more than just talking.

BennyCunningham: My brother's friend at Exeter told me there's a new girl at Waverly who's a stripper from NYC.

HeathFerro: ?!?

BennyCunningham: Yep. Some club named . . . Hen Party? Chicken Hut? Horse Stable? I think in Brooklyn? I had my cousin who lives in the Village look it up—it's the kind of place where u take it all off. Thong included.

HeathFerro: When can I meet her?

BennyCunningham: Heath, you're nasty.

HeathFerro: Don't you know it, baby!



"Right here is fine," Jenny told the cabdriver as soon as she spied the discreet maroon sign reading WAVERLY ACADEMY hanging from a tree next to a tiny, one-story brick building. Waverly wasn't far from the train station, but Jenny hadn't been able to get here fast enough.

"You sure?" The cabdriver turned around, revealing a thin beaky nose and a faded light blue Yankees cap. "Because the front office is—"

"I'm a student here," Jenny interrupted, feeling a thrill ripple through her chest as she spoke. "I know where the front office is."

The cabdriver threw up his hands in defeat. "You're the boss." Jenny handed him a twenty, stepped out of the cab, and looked around.

She was here. Waverly. The grass seemed greener, the trees taller, and the sky cleaner and bluer than anywhere she'd ever been before. There were lush evergreens on all sides, and on her right was a wide, cobblestone path snaking up a hill. A green field spread out to her left, and in the distance a few boys in Abercrombie fatigue shorts were kicking around a soccer ball. The whole place smelled


On Sale
Nov 2, 2005
Page Count
272 pages

Cecily von Ziegesar

About the Author

Cecily von Ziegesar is the creator of the #1 bestselling Gossip Girl and #1 bestselling It Girl novels. She has always lived in New York City.

Learn more about this author