There were the popular girls dressed up as scantily clad rock stars. They always looked as if they’d been born beautiful, with perfect hair and perfect smiles from the day they’d come screaming into this world. Wandering nearby was a boy dressed as Hugh Heffner. The football guys sported black spandex shorts, complete with a pair of socks shoved down their pants in just the right spot. Annie also spotted pirates, cowgirls, and farmers. Six girls were dressed like pumpkins and strawberries. They weren’t sexy like the popular girls, but goofy with fake white leather boots, pink or orange wigs, and matching A-line velvet dresses straight off the rack at iParty. Annie wasn’t impressed by the idea of a store-bought costume, but she would have worn one if it meant she could have been a strawberry, a pumpkin, or anything else, just to be in their group.

A senior in Pryce cruised past Annie on a skateboard — or, more realistically, was tugged by another senior girl. These two were part of the Pryce Girls, a popular clique of seniors in the boarding community. They both had bumblebee headbands, though their matching head-to-toe tie-dyed outfits were far more noticeable, especially to Annie, who couldn’t believe they tried to upstage their dorm’s chosen costume theme. But the Pryce Girls were confident and daring.  From time to time they ran around topless on campus at night, and once attended chapel services wearing nothing but their winter coats. Annie thought they always looked like they were having the time of their lives.

Annie regarded the two girls thoughtfully, somewhat resentfully, knowing there was once a time when she was set to become one of them. She and the Pryce Girls were now pretend friends, but Annie had been part of the clique when she first started at Milton. Most of the girls were just like her: white, upper-middle class, and obsessed with boys, magazines, appearances, and kissing. The similarities were comforting, but Annie had watched the gulf grow larger between the Pryce Girls and her after freshman year.

When I was drunk I did this, the girls would say.

            Oh, I love doing this sort of alcohol.

            Oh, I love tequila shots!

            What’s tequila? was all Annie could think to add.

She realized that there were social milestones and she’d already missed a big one. By junior year, most of these girls had been to parties, smoked weed, had boyfriends, and lost their virginity. Over time, Annie wanted more than a group of friends who looked and spoke and sounded just like she did. The friends she had senior year were quieter and interesting. They were white, black, and Asian, some from countries she’d never been to, and had life perspectives and experiences that were completely different from her own. Her best friend, Ida, held a prestigious leadership role at school. She was better than a Pryce Girl — a unifying force in the senior class and friendly with everyone, or at least that’s how Annie saw it. Annie genuinely loved Ida, but she never quite got over the loss of a well-defined friendship circle.  Even at a school where students were raised to believe in their unique talents, there was always the desire to be associated with a particular clique — to be tagged as a jock, a popular girl, or an artsy boy, even if it wasn’t the identity you preferred. Having a group was better than having no group at all.

The ultimate achievement, of course, was being singled out from that group — the popular one, the pretty one, the most kissable one. Despite her efforts, Annie had spent all of high school perfecting the art of contentment. To her classmates, she was nice and sweet, and she could accept that fact — to a certain extent. Now, on the eve of her senior year, she couldn’t face another year without a Milton boyfriend, or at least a boy in her life. Annie knew how reputations worked. They can be based on friends, sports, and accomplishments, but they’re intrinsically tied to who you date, who you hook up with, and how far you go.

While growing up in Lenox, Massachusetts, Annie got attention from boys for all the wrong reasons. They pinched her butt and liked her body, but they also made fun of her for being ambitious and hard-working. Annie grew up taking honors classes and studying flute. Lenox is a creative environment, the year-round home to Tanglewood and the summer home to the Boston Symphony Orchestra; it was here, under the steady guidance of her stay-at-home mom and her doctor dad, that Annie excelled wildly. She couldn’t wait to go to Milton. From what she understood, it was a place where it was cool to be smart and an individual; where she wouldn’t have to balance her studious and ditzy sides depending on who she was with.

Sometimes Annie couldn’t believe that she had yet to have a single Milton boyfriend. Despite her accomplishments as a musician, leader, and dorm confidante, nothing distracted from this personal social failure. More than anything — more than standout SAT scores, a top-tier college, or straight As — Annie wanted to be pursued, adored, and desired. It didn’t make sense. She was pretty, wasn’t she? Maybe not drop-dead gorgeous, and certainly not as thin as the more popular Milton girls, but she was definitely pretty. A talented flutist. A devoted friend. Everything about her screamed  I’m a nice girl, I have a cheery personality, and I work hard.

Annie wasn’t completely inexperienced, either. She’d had boyfriends before, so she’d been validated as a girl who could have a boyfriend, and understood what it meant to kiss a boy, hold his hand, and do a little more. For two long years, she’d been hooking up with Scott, a public school guy from her hometown. She first noticed him when they were in middle school; he was a year older, had great hair, and played on two middle school boys’ varsity teams. He was also dating the prettiest girl in Annie’s class. She didn’t think she had a chance. But rumors circulated that he actually liked her back, and during her years at Milton — over summer breaks and school vacations — Scott and Annie hooked-up. For kids at Milton, a hookup meant many things; a kiss, groping, no shirt, no pants, underwear on or off, everything but sex. For Scott and Annie, hooking up usually involved oral sex (on him, not her).

Even though Scott didn’t call enough, like her enough, or treat her well enough, his limited affections made Annie feel wanted. But what she longed for most was attention from a desirable boy at Milton. As a senior, she realized she had one final chance to find social success. On this morning, behind the curtain, she twirled the starfish necklace her mother gave her when she graduated from middle school and waited for something to happen to her. She felt at once empowered and invisible. She loved the girl she was — honest, moral, hardworking — but guys weren’t attracted to these qualities. Nothing seemed to be changing.

Excerpted from "Restless Virgins" by Abigail Jones and Marissa Miley. Copyright 2007. Reprinted by permission of Harper Collins. All rights reserved.

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