The Uptown Boys
The story of how a crazy boy and his group of friends fell into my life.
The first time I met Charlie Monroe he offered to buy me a bag of peach rings. Well, that’s not entirely true. It’s more like I blackmailed him into buying me peach rings.
Here’s how our first real interaction ended:
“If you buy me those peach rings, I’ll hang out with you for ten minutes.”
“This isn’t a negotiation.”
I gave in. “Fine. Fifteen.”
“Shake on it?”
“Are we in middle school?”
Charlie smiled. “There’s nothing wrong with feeling like a kid again.”
He reached out his hand, and with a slight hesitation, I took it. And then, with his characteristic grin, he vanished from my doorway. I gazed out into the brightly lit hallway, confused, yet intrigued. This is the (mostly true, and mostly fictionalized) story of Charlie Monroe and the Uptown Boys.
Charlie Monroe came crashing into my life on a chilly late October evening. I was about to fall asleep until my ceiling start to shake. Gradually, at first, then escalating to a full on jackhammer. Being so close to the ceiling on my bunk bed, I could almost see the dust from the ceiling tiles fall onto me. After at least 30 full seconds of this, the banging subsided. I turned to my roommate to make sure that she had heard that too. She nodded at me, just as bewildered as I was. A couple of minutes later, there was knocking at the door. Sitting up on my bunk bed, I watched the door swing open to perfectly backlight three boys that I had never seen in my life before. I could only make out general appearances of the strangers — the one to the very left was really tall with some kind of dye in his hair, the one in the middle had shaggy long hair and wore a purple tie, and the one on the right was blonde with bags under his eyes. I stared at them.
Purple tie grinned. “You’re Chloe, right?”
“Do I…know you?”
He combed his shaggy hair off his forehead with his fingers. “We’re in the same history class. I’m Charlie. This is Ezra, and Miles.” He gestured to his friends on either side of him. The tall one mumbled a quick greeting, while the blonde one smiled sheepishly.
Charlie proceeded to tell me that he had seen me around campus and thought that I seemed interesting. After a chance encounter with me in the elevator (that I have no recollection of) he began to put a plan into action to find me. One day, he listened closely during roll call attendance to find out my name, and with that piece of information checked every single room on every single floor. Then, he decided the best way to actually meet me was to convince the poor girls who lived on the floor above me to jump, causing my ceiling to shake, because this would be an icebreaker to the conversation. So, would I, with him and his friends, like to hang out tonight?
I could barely contain my laughter, and I couldn’t believe this was actually happening to me. “You know that’s extremely creepy, right?”
Charlie nodded. “I guess. It caught your attention though.”
I considered this for a minute. On one hand, this was by far the weirdest thing that had ever happened to me, and if I was in my right mind I would’ve slammed the door on his face, but on the other hand, I was kind of flattered by how much effort they had undergone to find me. Plus, I was intrigued by what kind of person you had to be to even come up with this idea.
“Will you do something for me to make up for it?”
“If I do it will you hang out with us?”
I shrugged. “Sure. Bring me the peach rings by our next class, Tuesday.”
Not even two hours later, there was a knock on my door.
“You don’t need to hang out with us tonight,” he said, dropping the peach rings onto my hand. “But you owe us a favor.”
I didn’t have time to respond before he vanished. That was when I knew this kid was like no one I’d ever met before.
At class the next Tuesday, he sat behind me and threw a set of keys at me when I didn’t hear him calling my name to get my attention. He just waved at me, saying no words. The next couple of times that I saw him around campus were just as weird, with him not having anything to say but simply wanting to get my attention. Riding the elevator in awkward silence together, running into him when he was creating mischief around our building, spending too long on the 7th floor to want to go unnoticed by me, things like that. He was like a child without adult supervision during recess, parading around in a cloud of recklessness. A week after his first visit, he knocked on my door, flanked by his posse.
“Will you hang out with us tonight?”
I thought about this. There really was no harm in it. And besides, I was intrigued by them.
“Really?” Charlie’s surprise was nearly tangible.
“Yeah. Let me just get shoes.”
My roommate turned to me, shaking her head and whispering warnings at me. I waved her off, and with no hesitation, I headed out the door with Charlie Monroe.
My first night out with Charlie Monroe and his group of friends that I like to call the Uptown Boys was exactly what I’d expected it to be, and completely unexpected at the same time. As we walked outside, Charlie said, “I don’t know you at all. Tell me about yourself.”
“That’s the most broad thing you could’ve asked me,” I said, laughing. “Do you want the Tinder bio version of the story of my life?”
“No. Like who are you? What are you into?” He lit a cigarette and took a puff, offering it to me. I waved it away. “I want to know everything there is to know.”
“That’s unfair. You go first.”
“Alright. If you insist.”
Charlie was from Dallas, Georgia, a borderline rural town a couple of hours away from Atlanta, and his Southern accent comes through when he gets excited or high. He was never out of stories from his life back in Dallas, and made it very clear that he missed it, and not just because the age to buy cigarettes there is 18. As we walked through the North End in the dead of night, he launched into a tale about how, as a child, he had to rescue a neighbor’s cat from the Dallas sewer system. Being the smallest kid in elementary school, when his neighbor realized that his cat had somehow gotten into the sewer, he was the first to be nominated to go retrieve it. So, like a Teenage Mutant Ninja Turtle, he climbed into the sewer drain and rescued the animal.
I laughed. “No way.”
“It’s true!” He said, and turned to his friends. “I only tell the truth.”
The tall one, who I figured out was Miles, snorted. “You never know with Charlie.”
Ezra nudged me. “Don’t trust a word he says.”
“Listen, that’s just how it was in Dallas. Last summer, I wore a fanny pack every day that only contained the basic necessities: kleenex, band aids, flare gun, switchblade, and a little vial of cocaine.”
“What?” I exclaimed.
“You know,” he shrugged. “Just in case.”
It was obvious by the way the boys hung onto every word of his tales that Charlie was the unofficial leader of the group, taking the boys through his journey of mischief and recklessness. The group, or the Uptown Boys as I like to call them, consists of the three original members -- Charlie Monroe, Ezra, and Miles. I never learned Ezra and Miles’ last names in the nearly two-month span that I spent with the Uptown Boys, and their archetypes as sidekicks fit them both too perfectly for me to ask what their last names are. Ezra is an obnoxious bleached blonde (a decision made during a random weeknight last September), and he is the most girl crazy person that I know. Crushes for Ezra turned into full blown love, or at least what he considered was love. One wintry evening, he dragged Charlie and I to walk over to Wentworth, a 40-minute excursion, just so he could have a chance to maybe meet a girl that he was talking to on Tinder. Another time, he came up to me in the college dining hall, and handed me a flyer — a written invitation to attend a party that he was throwing in order to celebrate getting 500 Tinder matches. Charlie and Miles once calculated the number of girls that Ezra had exclaimed that he was in love with had to be well into the 20s by now. Despite being girl crazy, Ezra was well meaning and knew his limits.
The other original member of the Uptown Boys was Miles. Miles was a tall kid with subtly dyed purple hair (another random weeknight decision) with a genuinely kind soul. He was the moral compass in the group, holding off Charlie when he got too crazy, making sure that Ezra didn’t cross the line. Sometimes, when I’d run into them, Charlie and Ezra would run ahead first, with MIles walking behind them like a calm parent trying to control his rowdy boys. Even as the gentle giant and father figure of the group, he participated just as much in the mischief as the rest of them.
But back on that first night, I didn’t know who these boys were that were leading me onto a bridge on the far North side of town. We climbed up the barrier to reach a rooftop overlooking the commuter line train rails. As we walked across the rooftop, I marveled at the view of the Boston skyline from the North side of the city. A train passed by below us, and the boys waved at the conductor, whooping and yelling when he waved back at them. I laughed to myself.
“What’s so funny?” Charlie asked, coming up behind me.
“Nothing.” I shook my head, trying to figure out how to explain my thought. “It’s just that you guys are like… the Uptown Boys. You know, we’re technically uptown of the city, so… the Uptown Boys.”
Charlie stared at me for awhile, with a completely serious expression before breaking out into a grin that spread across his whole face. “That’s fucking hilarious. I’m gonna use that.”
After Charlie smoked another cigarette on the rooftop, we headed back home with Charlie telling stories all the way through. He told me about how he once lit a flare gun off in a Hilton Hotel in Atlanta, and was now banned from every Hilton in the world. He recounted the day that he tried to steal a bottle of wine from Target but was caught by the Target security, found himself detained in a secret back room, but somehow was able to charm himself out of getting into any real trouble. He told me about how he found a sailor hat at his very first college party and now wears it to every single one, and how he once tried to dress like John Lennon for a week straight, and how he crashed a Harvard Finals Club, and how he stopped taking his bipolar meds because he felt like they stifled him, so he just got up to as much mischief as he could instead. The boys hung on his every word, interjecting their own thoughts and anecdotes in between Charlie’s stories.
When we finally got home, I met some of the other unofficial member of the Uptown Boys. Sam and Noah were Charlie’s roommates, both relatively calmer than the core three, but still appeared on occasion. Both Sam and Noah were the most impressionable and gullible people that I’d ever met, and Charlie had figured this out very early into their relationship.
“Sam, get me a glass of water,” Charlie shouted at him as we piled into the suite, his Southern drawl apparent.
“No, I’m about to go to bed,” Sam groaned, rolling over on the couch.
“Come on,” he whined.
“Fine, but this is the last time,” Sam said, standing up.
Charlie winked at me and I laughed. Someone put on a movie, and the boys gathered around to watch it. I lost track of time until it ended and I realized that it was past 2 AM. I collected my things and went to leave before Charlie called after me.
“We’ll see you again, right?”
I hesitated. “Only if there’s more peach rings in it for me.”
He shook his head. “What’s with you and peach rings?”
“I don’t know. It’s the first candy that came to my head.”
He smiled. “Fair enough.”
I did end up hanging out with them for two months after that, tagging along on their adventures, hearing more of Charlie’s crazy stories. But like most of the people in their lives who weren’t the core three, I drifted away from the Uptown Boys. The Uptown Boys are still friendly with me — they’ll say hi in the hallways. Sometimes, when Charlie thinks about me, he drops off a bag of peach rings as a reminder of the good old days.