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The Matchmaker's Match

Chapter 1

Chapter 1

Jun 09, 2024

Milo

Of course I was curious about the gift box I found near my locker the moment I saw it, but it’s not until I sit down at my usual table in the cafeteria and open the lid that it truly surprises me. My first instinct is to shove the lid back on the box and pray no one around me in the busy cafeteria saw what was inside, but the gift itself is so gorgeous, so utterly tantalizing, that I can’t help but to stare down at it, taking in the pictures and colors and the all-too-familiar font scrawled on the cover of what seems to be a first edition Dungeons and Dragons Dungeon Master’s Guide.

I’m dumbfounded by the gift; like, I’m totally speechless. Not that there are many people I can really talk to about a book like this. While I love being a Dungeon Master with a small, curated group that meets nearly every Friday and Sunday, this is a part of my life that I don’t exactly tell everyone at school about, for obvious reasons. Playing D&D every weekend isn’t exactly the best way to maintain my status and popularity and high school would be infinitely harder without my carefully crafted image intact. I love Dungeons and Dragons and the friends I play with, but not as much as I love being on top of the food chain around here.

After a quick look over my shoulders to make sure no one’s paying any attention to me, I turn the book over and read the back cover, devouring every word. I can’t help but succumb to the temptation of opening the book right here in the middle of the cafeteria. The pages are filled with the worlds and stories that provide an untold number of characters and plot lines to help create new campaigns. This book is really going to up my game—I can tell already.

“Um, Milo?” Talia says as she takes the seat next to mine. She raises her eyebrows as she takes in the book in front of me. “What is that?”

“It’s exactly what it looks like,” I say with a sigh.

“That’s what I thought,” she replies. “So what are you doing with it in the middle of the cafeteria? I thought being a Dungeon Master was your one adorable, little, nerdy secret that you decided to hide from everyone at school? Don’t you have long-standing personal rules about letting that particular freak flag fly?”

I glare at Talia as I carefully place the book back in the box. She may be one of my closest friends, but she can really get under my skin when she wants.

“I didn’t break any of my rules,” I assure her, keeping my voice down. “I didn’t bring this thing to school—I happened to find it wrapped up as a gift by my locker.”

Talia looks up at me, her eyebrows still arched in confusion.

“Um, don’t you think that’s weird?” she asks. “Or is this Anthony’s way of asking you to the fall dance?”

I put the lid back on the box, rolling my eyes.

“Who says I’m going to the fall dance?” I scoff.

When I look up at Talia again, I see that she’s not looking at me anymore but has her gaze directed somewhere across the room. Following her eye line, I see that she’s looking at a guy I don’t know, who is sitting by himself a few tables away from ours.

“Do you know who that is?” Talia asks. “He keeps looking over at us—or rather, at you.”

My lips immediately turn down into a scowl as I get a look at the boy, wondering who he is. I’ve never seen him before, which is saying a lot since I make it a habit to know everyone at this school. I serve as an unofficial matchmaker for anyone looking for the perfect long-term relationship, prom date, or casual fling. In order to set people up with an appropriate match, I need to stay on top of the student body. This new kid is a complete mystery to me.

The next time he looks up, our eyes meet and he quickly looks away, giving me a chance to really observe him. It’s hard to tell how tall he is while he’s sitting, but his long legs tucked awkwardly under the cafeteria table suggest he’s probably pretty tall like I am. He has olive skin and penetrating dark eyes that are hidden behind large-framed glasses. As I give him another glance, I think that he’d be actually kind of cute, if he ever decided to wear contacts and dress in something other than flannel.

“He keeps looking at you,” Talia says, her eyes searching my face for a reaction. “Maybe he’s your new secret admirer.”

“I doubt it.” I laugh, shaking my head. “I don’t think he looks like the type.”

“Then who gave you the book?” Talia asks.

I glance down at the box, wondering that exact same thing.

“It’s probably from Anthony or Gabe.” I shrug, trying to play down the mystery.

“Yeah, I don’t think so.” Talia laughs. “Neither of those two has the brain cells to think of a gift this thoughtful. I mean, I thought that your gay fan club didn’t know that you’re a regular Dungeon Master, right?”

“Right,” I mutter, glaring at Talia. “But can you please keep your voice down? After all, I have a reputation to uphold.”

“Exactly, which is all the more reason to find out who gave you that book,” she points out. “Your reputation is at stake!”

I let out a long sigh, knowing that she’s right, but I still doubt I’ll do anything about it.

“I don’t see the point,” I tell her. “I’m the matchmaker, not the person who gets matched.”

Talia sweeps her hair up into a ponytail on the top of her head and holds it there for a moment as she lets out a loud, patronizing laugh. As she lets her hair fall back down to her shoulders, she points an accusatory finger at me.

“You know, I think that you might be the one person in this school who knows the most about love and making matches, except when it comes to your own life.”

“Whatever,” I mutter.

“Come on, prove me wrong, Milo,” Talia continues. “I dare you to go talk to that new kid on the block over there.”

“For what purpose?” I huff, wondering what’s behind the dare.

“To prove my point,” Talia says.

“Which is?”

“I think that being the school’s number one matchmaker is just a defense so you never have to find love for yourself,” she says, turning on her chair so her whole body faces mine. “It’s always so much easier for you to have an opinion on other people’s love lives than it is to have a love life yourself. I’ve seen you flirt and tease and do the whole Milo show—”

“Excuse me? The what?” I interject.

“You know, your whole bit,” she says. “You’re popular and you have a huge circle of friends, and you set other people up on these dates that quickly turn into iconic matches. I mean—how many couples in the homecoming court over the years did you match together?”

“All of them since I’ve been in high school,” I mutter.

“And you do it out of the kindness of your heart,” Talia coos, clasping her hands together and batting her eyelashes at me.

“I do it because I’m good at it,” I say with a shrug. “That’s all.”

“Milo—you’re even going to land the main role of Cyrano de Bergerac in the fall play!” Talia points out. “Have you considered the irony of you playing Cyrano?”

“I don’t know what you’re talking about,” I argue. “And if you don’t mind, I’d like to eat my lunch instead of listening to whatever this lecture is all about.”

“Cyrano de Bergerac,” Talia continues, ignoring me completely, “hides himself from love by pushing someone else toward it. The role was made for you.”

“Fine, whatever,” I groan. “Look, I don’t really need to prove anything to you or anyone else, but I’m going to take your dare just to prove you wrong so you’ll shut up about it. I’m tired of hearing you talk.”

Talia laughs and replies, “Whatever.”

Standing up from the table, I give my head a shake and head straight across the cafeteria to where the new kid is sitting. As I approach, he looks up at me and adjusts his glasses, pushing them up to the bridge of his nose.

“Hi,” I say confidently, holding out my hand to shake his. “I’m Milo Ripley. And who are you?”

The boy frowns at me, his eyebrows furrowing with confusion and even displeasure at the sight of me.

“I’m sorry,” he mutters practically under his breath. “Why are you…why are you talking to me?”

AbbyLittles
Abby Littles

Creator

Comments (11)

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jauxro
jauxro

Top comment

ok. Awkward. 😬 that really shatters his main character moment. But hey, since he's popular, he should be able to say something smooth instead of getting flustered??

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To the untrained eye, high school senior Milo Ripley kind of has it all. He’s hot, he’s fluent in several languages, he’s gregarious and he’s smart as hell. He’s also beloved, because he’s the school’s resident matchmaker. But when it comes to finding love for himself, it’s a whole different story; Milo’s never been in love. But when he receives an anonymous gift from a secret admirer who seems to know him very well in the sweetest ways, Milo can’t help but become intrigued. Could this person be the one? Determined to find out who the admirer is, Milo turns to a new friend—shy, soft-spoken, bookish transfer student and amateur investigator Matteo—for help.

Matteo’s got a bit of a secret of his own—he’s Milo’s secret admirer. The one time he decides to be bold! He’s too scared to admit the truth, so he tries to help Milo find his mystery man…even though it’s actually him. Because there’s no way a popular guy like Milo would ever want to be with a wallflower like Matteo…right?
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Chapter 1

Chapter 1

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