The Most Awkward Conversation I Ever Had

My high school wasn’t very diverse. We measured ethnicity in halves and quarters, e.g., “Well Sabrina is black, and Greg is half-black, so that’s one-and-a-half black kids at three-quarters black on average.” In the classrooms we practiced Algebra and Geometry, in the cafeteria we practiced the Math of Racial Insensitivity.

Then, my Senior year, Jeremy arrived.

Jeremy transferred in as a sophomore, and I wish I could say that he was able to change things. He wasn’t. If anything, he made things worse for the remaining fractions of black students. In fact, the rumor I heard was that he was only half-black, adding to the already-confusing mathematics and pushing the rest of us whiteys further from tolerance.

Jeremy, or Jay-Money (as he preferred), considered himself to be “ghetto fabulous”. The rest of the school considered him to be N-rich (I’ll spare the racism)–yes, he lived in a mansion, but it was a rental.

Jay-Money loved attention, and he loved being the chocolate sprinkle on an otherwise vanilla bowl of ice cream. You’d see him dancing or singing around the hallways, wearing his gaudy sunglasses and his diamond chains. His showmanship earned him a following, but his need for approval led to some obnoxious antics. He was operating under the mentality that it was better to be laughed at than ignored, without realizing that he was reinforcing stereotypes and becoming a pariah in the form of a one-man minstrel show. I pitied him.

Jay-Money had his friends and his enemies. He had a girlfriend who seemed to like him less for his good looks or his personality and more for the look on her father’s face when she brought home a black guy. There were frequent run-ins with the “hard” white kids who wore baggy pants, listened to rap, and smoked cigarettes across the street from school every morning. One time there was even a fight, which was described by an eyewitness as “Not so much punching as just dancing in circles around each other.”

High school wasn’t kind to Jay-Money, and his behavior only made it worse. About three-quarters through the year, it was decided (by Jeremy? by his father? I’ll never know) that he wasn’t going to attend Point Beach high school anymore. The following fall he’d be transferred to Rumson-Fair Haven high school, a school somehow richer and more intolerant than my own.

In the meantime, Jay-Money was left to his own devices. His activity of choice seemed to be loitering for several hours around the Plaza Deli, a small restaurant about 3 blocks from high school. The Plaza was a popular lunch spot for students and delinquents alike.

The way the Plaza worked was very inefficient: you’d walk in, order, pay, then be given a ticket with a number on it. You’d go into an adjacent room to find a seat, then periodically someone would walk through with a tray full of items and call out the order numbers. The menu was limited at the Plaza, and a tray full of food brought into a room of hungry adolescents always ended in a feeding frenzy.

In an effort to save money, I would bring lunch from home. When my friends and I would go to the Plaza, I’d stake out a seating arrangement while they stood in line to order and pay. I usually packed a light lunch, and would always be nearly finished by the time they were done.

One day, I walked into the seating room and was alone, save for Jay-Money and a few Hispanic cronies I’d never seen before. They were sitting at the back table, talking loudly and laughing. Suddenly, Jay-Money turns to me abruptly. He looked at me with familiarity, despite the fact that we’d never spoken.

“Yo, who you datin’?” he asked. I was dumbfounded by the question.

“What?”

“I said, who you datin’?” he repeated the question with emphasis, as if it would make the sentiment any less confusing.

At the time, I was seeing a girl named Julie who went to a different high school. I was certain he didn’t know her. Up to a moment prior, I was certain he didn’t know me.

“Oh, just this girl,” I said. “She goes to Shore Regional.”

“She got a name?” He was all of a sudden very interested in my love life.

“Her name is Julie.”

“Oh, okay,” he said. “For a minute, I thought you didn’t know her name, and I was like, ‘What if you’re hitting that and you don’t know her name?’ It’s like, ‘Oh! Oh! Oh!…I’m sorry, what was your name?’”

The “Oh” noises were intended as sex moans, and as he did it, he gyrated his body in what I was to assume was doggy-style sex pantomime. Either that, or he was demonstrating his skills as a potential rodeo cowboy.

His friends all thought it was hilarious, cackling between bites of cold French-bread pizza. As for me, I was so befuddled at what just happened that I was speechless. A moment later, just a moment too late, my friends came in and sat down. They all asked why I looked so strange.

“I just had the weirdest thing happen,” I whispered.

Now it later occurred to me that I ate lunch with the same group of friends every day, all of them female. Jay-Money probably assumed I was dating one of them. Perhaps he was attracted to one, or multiple, and was asking who was and who wasn’t off-limits. The motivations behind the conversation could have been completely legitimate.

Nevertheless, that doesn’t change the fact that it was singlehandedly the most backwards attempt at interpersonal communication I’d experienced prior or since. If that day taught me anything, it’s that the easiest way to confuse someone you’ve never talked to before is to yell, “Yo, who you datin’?”

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