A full third of the students in my freshman class at college were either from New York or from one its numerous surrounding regions (Long Island, Westchester, etc.). They constantly talked about “The City,” and how great it was, and how they could barely stand the fact that they weren’t there at this very moment. (For the record, the college was located on top of a verdant hill about four hours north of The City.) When I’d admit that I’d never been to New York, they’d narrow their eyes and cock their heads to the side, like dogs who’d heard a shrill noise. Then they’d say something like, “WHAT DO YOU MEAN YOU’VE NEVER BEEN TO THE CITY?” Before I’d have a chance to answer, they’d inevitably wave over a few of their friends so that more people could poke at me and have a look at The Guy Who Had Never Been To The City.

Most of these people had come directly from tony prep schools exactly like the one in Dead Poets Society. I was genuinely surprised to learn that such places didn’t exist exclusively in movies. While I’d been busy making an endless string of ashtrays in vocational shop class during my public high school years, these people had been wearing striped neckties to Latin class and swimming for the varsity squad. They’d arrived at college driving tiny sports cars that they owned. I’d arrived in my father’s boat-like van, the one with the single circular window in the back. They had huge bongs stashed in their antique steamer trunks. I had an afghan that my mom had crocheted for me. Clearly I had some catching up to do here.

While our mutual foreignness somewhat dissipated over time, it would still, on occasion, come roaring back during unexpected moments. One night, on my way to pick up a girl for a date on the far side of campus—the sole date I would have in my four years of college—I encountered a group of my classmates who immediately doubled over with laughter as soon as they spotted me. “What on earth are you wearing, Jones?” they asked. My outfit—a combination of blue jeans and a jean jacket, which I felt confident and comfortable in—was, in their vernacular, known as a “Mexican tuxedo.”

I told them to go screw and kept on walking. But my face was already hot with shame. I cursed myself out, wondering why I didn’t possess the savviness and the foresight not to cover myself in denim as I had. You goddamned fool, I thought. I looked at my watch. It was too late for me to return to my dorm to change into something else. I had no choice but to press on with my evening.

The girl’s name was Maxine. I’d met her at a keg party in the dimly lit basement of one of the fraternity houses. Girls terrified me at the time (and, to some degree, still do). Talking to one who I found attractive had the curious effect of instantly making my breath sour. Forget trying to hold up my end of the conversation; if there was an attractive girl within five feet of me, my breath could suddenly loosen shingles off the roof of a house.

“Ask them if they want to go to the coatroom and make out,” a classmate named Phillip once advised me. “If they ask ‘when?,’ you say, ‘Right now.’ ” Phillip lived alone in one of the few singles on campus. He doused himself in exotic colognes and took trips to Italy over Christmas break. He was the Warren Beatty of the school. “Girls like that for two reasons: one, because it’s honest, and two, because it’s simple. That’s all girls want—someone to pay a little attention to them, and someone to make out with.”

The best I could hope for was to ambush one of them in a dimly lit basement and, instead of saying something cool per Phillip’s instructions, I would very quickly—before my breath could sour completely—do the gentlemanly thing and ask her out on an old fashioned date. In the case of Maxine, I asked her if she would have dinner with me on Sunday night at the Chinese restaurant in town. As soon as she said yes, I promptly set down my plastic cup and made a beeline for the basement door, certain that saying one more word to her, or, God forbid, having a proper conversation with her, would only further diminish myself in her eyes and give her reason to reconsider.

Maxine answered the door wearing a short black dress. She had a turquoise barrett in her black hair. Her skin was as pale as tapioca. I studied her face, looking for signs of judgment regarding my all-denim outfit. I didn’t see any, which made my confidence return. The hell with those guys and their Mexican tuxedo, I thought. On our way to the restaurant, I chewed at least seven sticks of Big Red in an attempt to keep my bad breath at bay, at least for a portion of the evening.

The Chinese restaurant was empty on a Sunday night. Maxine ordered a vodka martini, which seemed incredibly sophisticated to me. From the moment we sat down, I was on edge. I’d had eaten perhaps four dinners with girls in my lifetime at that point—and two of those dinners were with prom dates in high school. But Maxine looked across the table at me as if she’d been looking at men across restaurant tables her entire life. As always, I clearly had some catching up to do here.

I grilled Maxine on her classes that semester (political science), her homework habits (early mornings and late nights; she used the word “useless” to describe her brain in the middle of the day), and her roommate (a snorer from Florida named Amy).  “I’m tired of listening to myself talk. Let’s talk about you,” she said. She ordered another martini from the waiter. “Have you spent much time in The City?”

And there it was again—the most dreaded of dreadful questions. I told her that I had not spent much time in The City. “In fact, I’ve never been to New York,” I said.

Maxine’s jaw hung open for several seconds. Then she said: “WHAT? IT’S THE GREATEST PLACE IN THE WORLD.” Maxine had grown up on Park Avenue. When her parents were divorcing, she and her mother had lived at The Plaza for six months. “We had room service and watched The Brady Bunch everyday,” she said. “It was the best six months of my life.”

Maxine said that a group of her fellow New Yorkers were driving down—she called it “caravaning”—to The City over the October Break. “You should come!” she said, taking my hand across the table. “I’ll show you around Manhattan. My mom got the apartment in the divorce, and it’s huge, so there’s plenty of room for everyone there. We’ll go to Chinatown and Central Park. We’ll go to The Village. We’ll take you shopping for some decent clothes. You’re going to love it.”

The idea of going to New York with this martini-drinking girl was thrilling and terrifying at once. But those thrills and terrors were ultimately blotted out by the fact that Maxine had noticed—and judged—my all-denim outfit. Of course she had. She was no dummy. I wondered if I’d ever stop feeling like the school’s resident jug-blowing hillbilly.

I paid for dinner, counting out the bills from my wallet, realizing that I’d lost the upper hand here. Then Maxine said something that snapped me out of my downward spiral of self-pity: “Let’s go back to my room. Amy is out of town until tomorrow, so I have the place to myself.”

When we got to her room, Maxine fixed us both vodka martinis from a makeshift bar. Then she realized that she hadn’t really eaten much of her dinner and decided to order pizza and wings for delivery. She sat next to me on the bed, so close that the material from her dress rubbed against me like crepe paper, while she phoned the pizza place. She read the numbers off a credit card into the phone, then hung up. “It’s my father’s ‘in case of emergency’ credit card,” she said. “He’s such an asshole.”

I hadn’t realized how drunk Maxine was until she announced to no one in particular that she was going to take “a little nap,” then flopped backwards onto the bed like Joe Frazier going down against George Foreman and passed out. There was a knock at the door a few minutes later. The pizza and wings had arrived. In the claustrophobic confines of the tiny dorm room, the pizza smelled terrific. It was from Fat Frank’s, the place at the bottom of the hill. They had the best pizza in the world. I sat down in the wooden desk chair, opened the box, and took out a slice.

Maxine’s black dress had ridden up a bit on her thighs. Her white legs had parted slightly, just enough to reveal the smallest glimpse of her underwear. It was the same turquoise color as her barrette. I ate the pizza and continued to stare up her dress. Then I ate a second slice of pizza. Then I closed the pizza box and put a blanket over Maxine.

I tried calling her the next day, to make sure she was alright, but she didn’t answer. I called her again the day after that, and again each day for a week straight before finally giving up. October Break came and went. I wondered if she’d caravanned to New York without me. Then, two months later, as I was exiting another blurry keg party on a Saturday night, I spotted Phillip making out with Maxine in the coatroom. She had the same turquoise barrette in her hair.

I was apoplectic with rage. I shouted the words, “YOU’RE A WORLD CLASS ASSHOLE, PHIL,” sounding like a crazy person. Then I went home to bed.