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The Matchmaker's Match

Chapter 8

Chapter 8

Jun 09, 2024

Matteo

Well, damn, I think to myself, absolutely clueless about where to start. Not only do I have no idea how to run an investigation, but what’s worse is how to pretend to run an investigation when the person I’m looking for is myself. Right now, I need to put that piece of the puzzle aside. I still don’t know how this is going to come together, but in the meantime, I need Milo to trust that I know what I’m doing…which couldn’t be further from the truth.

Taking another sip of his Coke, Milo gives me a strange look as I tap the pen against the notebook he gave me, trying to think of what Veronica Mars would do in this situation. Where would she start? How would she go about opening the investigation?

She’d get the facts! a voice inside my head exclaims. Yes! The facts! That’s it. Trying to sound sure of myself, I hold the pen over the paper and turn to Milo, making my expression as serious as possible and hoping he can’t see how nervous I am.

“Why don’t you start by telling me the facts, Milo, just the facts,” I say.

Milo stares at me for a moment and then bursts out laughing, shaking his head as he pops another nacho in his mouth.

“You are hilarious, Matteo,” he says.

“Uh, yeah.” I laugh along uncertainly, totally missing the joke.

Was I being funny? I certainly wasn’t trying to be. I’m not sure what was so humorous, but if Milo thinks I told some great joke, then I guess I was being funny…though about what, I’m still not sure of. Who cares, though, as long as the hottest man alive is smiling at me!

“Look,” Milo says, polishing off the last of his snack as he gets down to business. “It’s no secret that I can date anything that’s walking on two legs in that school, minus the faculty, because, um, gross and illegal.”

While I’m trying to keep my face neutral, inside I am sighing dramatically. What chance do I have with Mr. Matchmaker when he knows he can have anyone he wants? This guy is everything. He’s Cyrano, but he looks like Christian. He’s selfless in trying to help people find love, to the point in which he doesn’t think it’s necessary to find his own love. He drives a beat-up truck, makes a mean plate of nachos, and loves reading more than TikTok, which is hard to find in a person our age. No one likes paper anymore. Everything is on a screen. In fact, it was the moment I saw Milo reading The Three-Body Problem that I knew it was love—because no one ever tries to read the book before the TV series comes out anymore. It’s all of the little contradictions about Milo that make him so impossibly attractive. And it’s how attractive he is that makes him so impossibly unattainable.

The thing about the Dungeons and Dragons book is that I didn’t really think too hard about it when I ordered it. I saw the first edition campaign and rulebook and I pressed the Buy Now button immediately. I haven’t personally played D&D since I was in middle school, and that was basically just so I could spend time with Jessica—she was the Dungeon Master to group back then—at least that’s how it started. I have some pretty amazing memories of those Friday nights, but not because I particularly loved Dungeons and Dragons. The main appeal to me was that after the campaign was over and we got bored and didn’t know what else to do, we would play Spin the Demogorgon and Jessica and I would end up kissing on the couch. Not a bad way to spend a Friday night.

That was back when my mother was still finishing her PhD and I was able to stay in one school for more than six months. I actually settled into that school, making friends and feeling like I belonged somewhere. That’s how I ended up dating Jessica for almost an entire year, though our eventual breakup had nothing to do with me moving and was all about when Jessica met Jen, who played a paladin in our D&D game. There was no denying that those two were meant to be and I didn’t stand in their way, despite being dumped. I was the biggest fan of their love story, and I knew they were meant to be.

Besides, things with Jessica had pretty much run their course at that point. The kissing was great, but we were also just best friends, which we remained even after our breakup. While she didn’t want me to hold her hand, she’d let me put her arm around her and there was something so reassuring about being close to her and knowing that I had a friend in the world. She would tease me relentlessly about how my hands could sweat like Niagara Falls yet my armpits were dry as the desert. It’s just one of my many quirks, I guess.

The thing about the D&D book, to be honest, is that I didn’t even know that Milo played. I was scrolling online for a new fantasy series, and it just popped into my feed. The cover was so compelling, and it brought back such good memories of my middle school friends that I clicked on the link and just stared at it for a while. Without even realizing it, I started picturing Milo’s face and I knew I had to give it to him. I can’t explain it. It’s like the book was somehow destined to be his.

“I’ve already crossed off the usual suspects from the list,” Milo tells me. “Talia, Anthony, and Gabe. They are the most likely to give me any sort of gift, but there’s no way that book came from any of them.”

“Why not?” I ask, interested more in Milo’s friends and what he thinks of them than why it’s unlikely any of them gave him the Dungeon Masters book.

“Just trust me on this,” he says. “Anthony and Gabe don’t know about my D&D game and would never even guess that it would be something I’d like. As for Talia, like I said before, she thinks D&D is a blight on my record and would never condone it.”

“Okay, so we can cross those three off the list.” I nod. “Who else could possibly have gotten it for you?”

“That’s what makes this so hard.” Milo sighs, crossing his arms over his chest. “No one else at school knows I play D&D.”

I nod, knowing I need to come up with some ideas about who the secret admirer could be, without letting on that it’s me—at least for now anyway.

“Well, who else is in your game group?” I ask. “Could it be someone you play with?”

Milo blushes at this—he legitimately blushes—and instead of looking embarrassed or uncomfortable, he actually looks hotter, like he just applied a gentle brush stroke of color to his cheeks to give them the perfect rosy glow. My god. No one should be this perfect.

“What is it?” I ask, wondering what has him blushing.

“Okay,” Milo says, sitting forward and clasping his hands together. “You have to promise not to laugh.”

“Of course, I promise,” I tell him eagerly, wanting desperately to hear his secret.

“I play with Ms. Green and our friends at the local community theater group.”

Milo looks at me like he’s expecting me to burst out laughing, even though I just promised I wouldn’t. To prove I can be trusted, I smile at him encouragingly.

“That’s cool,” I tell him. “I think it’s awesome you found people who share your interest.”

Milo laughs nervously, giving me an uncertain look like he doesn’t know what to think of me.

“I started hanging with them freshman year when I was new in school,” he says. “I auditioned for the community production of Romeo and Jules and was cast in the lead role.”

“Wait, Romeo and Jules?” I ask, interested in the change of title.

“Yeah, Anthony played the Juliet role that year,” Milo says. “He really wanted the part, and he crushed the audition, so they made the change for him. It was a brilliant production, man. Totally turned the story on its head.”

“That’s so cool, I wish I had seen it.”

“Well, after rehearsal one night, I stumbled on a small group playing in the dressing room and they were talking about being in a bit of a rut with their campaigns. I was interested in the game, how it was a combination of storytelling, role-playing, and fantasy, so I bought a book on how to play, and I quickly became hooked. Now we play on Friday nights.”

“I used to play on Fridays, too,” I say. “With some friends in middle school.”

“What role do you play?” Milo asks, leaning in with curiosity.

“Actually…” I laugh. “I’m the matchmaker.”

AbbyLittles
Abby Littles

Creator

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The gayest gay
The gayest gay

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OOooooooo Mr. Matchmakers Match is also a Matchmaker

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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 8

Chapter 8

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