Restless Virgins: Love, Sex, and Survival in Prep School

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Chapter One

Everyone's Watchin'
Everyone's watchin', to see what you will do
Everyone's lookin' at you, oh

—Lyrics from "Working for the Weekend," by Loverboy,
the song chosen by the class of 2005 for Senior Walk In

Eighties music blasted from a dorm room down the hall. Annie could hear it from her own room, where she sat up in bed and forced her eyes open, her wavy blond hair everywhere. It was early morning on orientation day at Milton, and she could already hear the other girls in Pryce House clogging the dorm's narrow hallways. They ran between bathrooms and bedrooms, screaming about summer romances and hugging as though it had been forever. I love your haircut! How was your trip? Did you go back to camp? Who do you wanna hook up with this year? Annie stared at the bare walls of her tiny single room, wondering how much she'd changed that summer and what would become of her that year.

Her first few days as a senior had been packed with the usual excitements and stresses: younger Pryce girls bombarded her with questions, orchestra and dorm commitments beckoned, and so did senior tasks, like checking in with the college office to continue calculating the ever-looming future. But Annie couldn't even begin to grasp the enormity of what she had to do that year: get good grades; perform with the full orchestra and chamber orchestra; take the SATs; pick a college; apply early to that college, which meant writing essays, filling out forms, and having an interview; wait to find out if she got into that college; prepareadditional applications in case she was rejected or deferred; pass exams; love senior year; find a way to drink and party over spring break; perfect her senior solo for the spring concert, which would take up at least three hours of practice a day; relish senior spring; make new friends; change her image; not obsess over boys; find a steady hookup, make him a boyfriend, lose her virginity, fall in love, or at least in like; and generally live up to the standards set by her civic-minded parents. Over the first few weeks of school, there were times when Annie came back to her dorm room at night, closed her door, and cried.

But everything always looked better in the morning, so Annie bounced out of bed, stumbling over piles of black-and-white posters of the 1920s and glossy Absolut vodka ads that she hadn't had a chance to hang on the walls. She put on vintage Madonna and riffled through her clothes. In about an hour, Senior Walk In would begin, a coveted rite of passage at Milton that took place at the first morning assembly of the school year, which was held on the basketball courts in the Athletic and Convocation Center (ACC). Seniors charged onto the makeshift stage from behind a curtain, wearing outrageous costumes, pumping their fists, proclaiming the start of the school year in front of the upper school. Annie remembered the first Senior Walk In she saw. She was a freshman and sat on the bleachers with the rest of the underclassmen, watching the seniors in Pryce prance out like confident leaders who knew exactly what they were doing. Now, after three years at Milton, Annie knew that appearances mattered. She wanted to assemble an outfit with the right blend of appropriateness (for the teachers), hotness (for the guys), and individuality (for herself). She was fleshy, a Rubens girl with a curvaceous body, breasts the size of baby melons since they'd first cropped up in fifth grade. She accepted her full figure. She had even come to terms with her acne, applying foundation over the pimples that marked puberty on her face. She'd always been reticent about her breasts, and still didn't understand how even they never garnered her attention from the guys at school.

She inherently accepted her social status: the aspiring socialite who had yet to expand her celebrity since middle school. Senior Walk In was her last chance to make another first impression at Milton. This was a moment of possibility. Some seniors' reputations already had been made, but change was not impossible. This was also a moment of vanity. Seniors considered who they had become (the jock, the academic, the prude) and what lasting impressions they wanted to leave with their friends and teachers. Because Senior Walk In was, after all, the genesis of their final teenage fate—the last year of high school.

Annie squeezed her thighs into a short black skirt and pulled a simple black shirt over her chest. She shuffled up to the mirror. The dimple in her chin was adorable and her cheeks were, as usual, a shade redder than she wanted. Annie liked her outfit. While some Walk In costumes materialized out of closets that very morning, Annie and the other senior girls in Pryce had started planning their outfits that summer, communicating over e-mail (Get your bumblebee headbands! Get something crazy!), and agreeing to be bumblebees because they'd each been willed a perky antennae headpiece with glittery yellow-and-black-striped balls from the girls who'd graduated the year before. Wills were a serious business among boarders. The night before graduation, seniors in each of Milton's eight single-sex dormitories passed down personal tokens to favorite underclassmen. Many boarders waited their entire Milton careers for this ritual, while underclassmen loved receiving coveted bequests that they then carried with them until it was their turn to pass them on.

Annie went to the closet to find the finishing touch to her costume, the bumblebee antennae she'd received the previous spring. They rested on a shelf above her hanging clothes, and were important because they were a status symbol that tied her to a specific dorm and a specific group of girls. On the morning of Senior Walk In, they quivered delicately each time she took a step, bobbing like a marionette, just enough to remind Annie that she, too, belonged.