Later that week, Mom came and picked me up early from Mt. St. Theresa’s, driving us forty-five minutes to The Bradley School, a coed, private, nondenominational institution located in the bowels of the lush, ivied Main Line. The admissions director made sure to mention, twice, that J. D. Salinger’s first wife had attended The Bradley School in the early 1900s, back when it was an all-girls boarding school. I stored that fun fact away, trotted it out for interviews with prospective employers and parents-in-law. “Oh yes, I attended The Bradley School—did you know J. D. Salinger’s first wife went there?” It’s okay to be insufferable as long as you’re aware that you’re being insufferable. At least that’s how I justified it to myself.

After the tour, I had to take the entrance exam. I was seated at the head of a regal table in a formal, cavernous dining room located in a wing off the cafeteria. The bronze plate above the doorframe declared it THE BRENNER BAULKIN ROOM. I couldn’t understand how anyone in the English-speaking world could be named Brenner.

I don’t remember much of the exam, except the part where I had to write a description of an object without ever explicitly identifying the object. I went with my cat, and ended the passage with her diving off our back porch to her bloodied, mangled death. Bradley’s boner for J. D. Salinger made me think they had a thing for tortured writers, and I was right. A few weeks later, we got word that my financial aid was approved and that I would be matriculating with The Bradley Class of 2005.

“Are you nervous, sweetheart?” Mom asked.

“No,” I lied out the window. I didn’t understand why she had made such a fuss about the Main Line. To my fourteen-year-old eyes, the houses didn’t look nearly as impressive as the pink stucco monstrosity Leah lived in. Taste, I had yet to learn, was the delicate balance between expensive and unassuming.

“You’re going to do great.” Mom squeezed my knee, the goop on her lips catching white sunlight when she smiled.

A row of girls, four deep, marched by our BMW, their backpacks firmly secured to their slight shoulders with both straps, thick ponytails bobbing like blond plumes on Spartan helmets.

“Mom, I know.” I rolled my eyes, more for myself than at her. I was dangerously close to crying, to curling up in her arms while she ran her long pointy nails up and down my forearm until I had goose bumps. “Tickle my arm!” I used to beg when I was little, snuggling up to her on the couch.

“You’re going to be late!” She planted a kiss on my cheek that left a sticky coating of lip gloss. In return, she got a sullen, new teenager “Good-bye.” That morning, thirty-five steps from the front door of school, I was still only in rehearsals for the role.

First period was homeroom, and like a huge dork I was excited by this. My middle school didn’t have bells or different teachers for different classes. There were forty girls per grade, divided into two classrooms, and in that classroom you were taught math, social studies, science, religion, and English by the same teacher all year long, and if you were lucky, you got the one who wasn’t the nun (I was never lucky). The idea of a school where a bell rang every forty-one minutes, prompting you on to the next classroom, with a new teacher, and a new concentration of students, made me feel like I was a guest star on Saved by the Bell or something.

But the most exciting part of that first morning was English. Honors English, another distinction my old school never made, in which I had secured a spot thanks to that brilliant 150-word description of my cat’s tragic demise. I couldn’t wait to take notes in the bright green pen I’d bought at the school store. Mt. St. Theresa’s made us write in pencil like babies, but Bradley didn’t care what you wrote in. Didn’t care if you took notes at all as long as you kept your grades up. Bradley’s school colors were green and white, and I bought a pen the same shade as the basketball jerseys to display my new allegiance.

Honors English was a small class, only twelve students, and instead of desks, we got to sit at three long tables, pushed together to form the shape of a bracket. The teacher, Mr. Larson, was someone Mom would dismiss as “hefty,” but those twenty extra pounds had resulted in a kind, full face: squinty eyes, a slight arch to his upper lip that made him look like he was remembering some hilarious crack one of his buddies had made to him the night before over lukewarm Bud Lights. He wore faded pastel button-downs and had the kind of floppy, light brown hair that assured us it wasn’t too long ago that he was a prep school kid just like us and he, like, totally got it. My fourteen-year-old loins approved. All the fourteen-year-old loins approved.

Mr. Larson sat a lot, usually with his legs stretched out in front of him, frequently reaching one hand behind his head and resting his skull against it, while asking, “And why do you think Holden identifies with the catcher in the rye?”

That first day Mr. Larson made us all go around the room and say one cool thing that we’d done that summer. I felt confident Mr. Larson had designed this exercise for my benefit—most of the other kids, “Lifers,” had been funneled from the Bradley middle school, and had probably spent the summer hanging out together. But no one knew what the new kid had been up to, and even though it just tanning on my back porch, watching soap operas through the window like a sweaty, friendless loser, they didn’t need to know that. When it was my turn, I told everyone I’d gone to the Pearl Jam concert on August 23, which hadn’t happened but also wasn’t a fabrication I’d created out of thin air. Leah’s mom had reserved tickets for us back before the whole pot fiasco, before she finally had definitive proof that I was the bad influence she’d long suspected I was. But there was an ocean between Leah and these new people, and I had some new friends to impress, so I lied and I’m glad I did. My one cool thing I did that summer invited several approving nods and even an actual “Cool” from some guy named Tanner, which I was surprised to learn was not just a goal I set for my skin that summer but also a name.

After that game was over, Mr. Larson wanted to talk about The Catcher in the Rye, which had been assigned summer reading. I sat up straighter in my seat. I’d torn through the book in two days on my back porch, my thumbs leaving humid half-moon imprints on every page. Mom asked me what I thought about it, and when I told her I thought it was hilarious, she cocked her head at me and said, “Tif, he has a serious mental breakdown.” This revelation shocked me so much that I reread the book, deeply concerned that this crucial element of the story had escaped me. For a moment I worried that I wasn’t the literary whiz I fancied myself, but then I reminded myself how Mt. St. Theresa’s eschewed literature in favor of grammar (less sex and sin in grammar), and so it wasn’t really my fault that my observations weren’t as sharp as they could be. I’d get there.

The boy closest to the marker board groaned. His name was Arthur, and that summer the coolest thing he did was take a tour of the New York Times office, which, based on the reactions of the classroom, wasn’t as cool as seeing Pearl Jam in concert but also not as bad as seeing The Phantom of the Opera at the Kimmel Center. Even I understood it’s not impressive unless it’s on Broadway.

“You enjoyed it that much, did you?” Mr. Larson quipped, and the classroom tittered.

Arthur was close to three hundred pounds, and acne framed his face like parentheses. His hair was so greasy that when he pushed his hands through it, it stayed, an oily arc from his hairline to the crown of his head. “Could Holden be any less self-aware? Here he is, calling everyone a phony, when he’s the biggest phony of them all.”