When I arrived in Connecticut at the station nearest Hillander, I asked the ticket clerk for directions and I walked three miles to campus. Along the way, I admired the golds, oranges, and browns that stretched along the tree-lined sidewalks, and I liked the crispness of the autumn air and how the wind caused the leaves to swirl around my feet. I have no idea how long it took me to get to campus, but I do remember the awe I felt when I arrived.
The towering gray stone buildings with venerable ivy-covered walls were just like the academies I pictured from books like A Separate Peace and Catcher in the Rye. I noticed a group of clean-cut boys crossing the quad on a tour, and I wondered which one would become my Holden Caulfield.
Everything was so different from Georgia. It was colder, for starters. I noticed that the people moved in a quick, serious manner, not slow and ponderous, like at home. Though it was fall, there was still plenty of greenery on the grounds, but whereas Georgia was emerald, Connecticut was pine. The dissimilarities alone showed me that I certainly had a lot to learn. But that was okay, because I loved to learn. I was hungry to know the world beyond hippie communes.
My excitement quickly melted away, however, the minute I arrived at my dorm. I’ll never forget the looks on the faces of my roommate and her parents when I stepped in the door.
“Hi! I’m Jill!” I said excitedly, as I tossed my duffel on the floor.
Their expressions displayed a combination of fear, horror, and having eaten bad shellfish.
“You must be Alissa,” I went on, despite the awkward silence.
“Yeah,” the girl answered numbly, as she and her mother simultaneously looked me up and down. Alissa was all angles and edges: straight, blunt-cut blond bob, with each hair perfectly aligned; sharp but pretty features—pointed nose, prominent chin, triangular cheekbones, big square white teeth. She was topped off by confident, narrow shoulders helming a tall, thin frame, and if it weren’t for her giant, round boobs, we probably even would have worn the same size.
But I was flat as a board and much more reedy all around. Plus, it didn’t look like we shared the same taste in clothing. Alissa wore a perfectly pressed plaid skirt and a neat navy crew-neck sweater. That, combined with her mother’s Chanel suit, and her father’s sweater-vest and bow tie ensemble, made my Goodwill turtleneck and carpenter pants look even more ratty.
“We’re the Fords,” her father politely said, snapping out of his own fugue state. “Of Boston.”
“Oh,” I said. “My parents were in Boston last year. For a Dead show.”
I noticed Alissa stifle a giggle then, as her mom opened the door and peered into the hallway. Her expression was more perplexed than ever when she pulled her head back in. “And where are your parents, Jill?” she asked.
“Oh, they’re in D.C.,” I explained. “They dropped me off at the train station there.”
Mr. Ford blinked. Alissa looked at me like I was growing another head. And Mrs. Ford’s face again went the fear, horror, shellfish gamut.
“Alone?” Mr. Ford asked. “You came up here alone for your first day of prep school?”
I didn’t see the big deal. I was used to doing things on my own. “Sure,” I answered weakly. Then I turned my attention to unpacking, trying to focus on anything but their stares.
Alissa and her parents did the same, diving into six suitcases and several large boxes. There was a bag of hair products, accessories, and styling tools; another bag of nail polish, compacts, lipsticks, and creams. There was one big bag just full of shoes—clogs, boots, loafers, sandals, sneakers, flats, pumps, slippers, and even golf shoes.
And then there were the clothes. Dozens of sweaters in colors I never knew existed. Skirts—short, long, midi. A dozen firmly pressed khakis, all the same color. Hangers full of starched oxford blouses. Cowelnecks. Turtlenecks. V-necks. Izods. Tenniswear.
“I don’t know where we’re going to put all of this in this tiny room,” Mrs. Ford harrumphed at one point.
“You can put some in my closet,” I kindly offered, since I had taken up only five measly hangers.
By the end of the hour, all of the closets and drawers were filled, but discomfort still took up most of the space.
Alissa looked so spooked at the prospect of living with me that I thought she might repack right then and there and follow her parents out the door. Instead, she stepped outside to bid her parents a tearful farewell. As they closed the door behind them, I couldn’t help but tiptoe over to hear what they were saying.
I quickly wished I hadn’t.
“It’ll be fine, honey, I’m sure,” I heard Mr. Ford mumble.
“I’m just not sure how I feel about my daughter living with a charity case,” was Mrs. Ford’s haughty reply, before another horrified sob escaped from their daughter.
And so I was marked from day one. A “charity case.”
For the next four years, I searched the campus up and down for anyone, girl or guy, to befriend. The guys wouldn’t give me a second look. They were rich, cultured, clean-cut, athletic and wanted girlfriends who were more feminine versions of themselves. The girls were all Alissa Ford clones, many of them Hillander legacies with family lineages that rivaled the House of Windsor. They treated me like if they got too close they’d catch poverty or, worse, unpopularity. They were confident, preppy, catty, and intimidating. It was an entire school of Ellen Cutters and Liz Alexanders. Even the less thin, less rich, less popular girls wouldn’t associate with me for fear of becoming even more unpopular.
They had a million nicknames for me. “Blue light special” referred to my Kmart wardrobe; they called me “Daisy Mae,” because of my southern twang; and when I dumbly, naively shared details of my upbringing, they started to call me “that Amish girl.”
I tried my best to change and fit in. There wasn’t all that much I could do about my wardrobe, but my hair took up a good amount of time. I went into town one day and got a cheap cut from the local barber school. I wanted graceful “wings” like the other girls in school. “Layer it like this,” I told the student, insecure with her scissors, while showing her a picture of Jaclyn Smith. I ended up looking more like Patti Smith. Then a week later, I tried to fix it with a perm that could only look good on a poodle.
I bought cheap make-up at Woolworth’s: pale pink lipstick, shocking coral rouge, fire-engine-red nail polish, midnight black mascara, and eye shadow—robin’s-egg blue, of course. Somehow, it never looked right, either, as much as I tried to copy the Hillander style.
My other attempts at fitting in were just as disastrous. I tried out for the tennis team, but even a fuzzy yellow ball could humiliate me. The rest of the school, it seemed, had been playing since in utero. Instead, I got really into music. On my lonely jaunts into town, I’d pick up a few cool used or remaindered albums at a dingy old record shop where I liked to kill time with the old hippie who ran it.
And I had a job at the library, which not only was great for extra cash, but it was where I’d always run into my secret crush: Walter Pennington III, a tall, handsome, and extraordinarily down-to-earth member of a high-profile political family. Walt had thick brown hair; a square jaw; and hallow, thoughtful eyes. But I fell for him because he had a layer of depth that no one else at Hillander seemed to have.
Walt was constantly checking out books, but not the usual guy books like Lord of the Rings, or anything by Robert Heinlein or Ernest Hemingway. He preferred reading the modern dramas of Eugene O’Neill, Tennessee Williams, and Edward Albee. But his absolute hero was Sam Shepard.
“They say he’s going to win a Pulitzer this year,” I said shyly one day when he checked out a copy of Angel City and Other Plays. Suddenly, Walter Pennington III, who never before noticed my existence, was talking to me.
Nearly