Page 7 of Falling for My Matchmaker (The Matchmaker Files #1)

Matchbox didn’t call it a party. They called it a Client Social Experience . Which sounded less like mingling and more like a startup trying to reinvent eye contact.

But it was a party. Rooftop venue, curated cocktails, a photo wall with giant foam hearts, and at least three women wearing red satin who looked like they hadn’t blinked since arrival.

I saw Emily, one of the Matchbox cofounders.

Alex, the IT guy, stood in a corner doing crowd scans like a human behavioral algorithm.

And Claudia, one of the senior matchmakers, was gliding through the room like a hostess-slash-high priestess, greeting people with cheek kisses and whispered gossip.

I was waiting for Brad to show up.

Our second date.

Nate had suggested it—gently, almost strategically. “It’s public, low-stakes, easy to exit if the vibe’s off. Good for observing how someone handles social energy.”

Which was probably code for: Bring your new crush to my office party so I can silently judge you both.

Brad, of course, said yes. I was starting to regret it, though—because I’d just stumbled into a conversation with a guy named Rob who looked like he came with a warning label and a whiskey endorsement deal.

Tall, broad-shouldered, masculine, just enough scruff to suggest he could both build a deck and emotionally process a breakup.

He wore a black button-down like it was part of his DNA. He extended his hand for a handshake .

“I’m Diana,” I said, shaking it. “Welcome to the dating factory.”

He laughed. “Is that what we’re calling it now?”

I shrugged. “Some people come out with love. Some come out with mild trauma and a Google Doc of red flags.”

“Fair,” he said, smiling.

We made pleasant small talk—work, weather, the predictable awkwardness of romantic networking events. He was easy to talk to. Easy on the eyes. If I hadn’t known better, I might’ve wondered if this was a setup. A Matchbox introduction, live and in the wild.

Then Rob glanced at his watch. “I should probably find my date.”

“Oh,” I said. “You brought a plus-one?”

He nodded then hesitated—just for a second. “Yeah. He was parking.”

I blinked. “You’re—oh! Cool. That’s great.”

It came out a little too upbeat, like I was auditioning for Ally of the Year. Not because I had a problem. Just because...I hadn’t seen it coming.

I’d assumed. The way he stood. Spoke. Made eye contact. It all gave “straight guy who shops at REI.”

Which, honestly, was on me.

“I think I see him now,” Rob added, waving someone over.

And then I saw him .

Nate.

In a fitted charcoal button-up, sleeves rolled up, hair slightly wind-tousled like he’d just stepped off a lifestyle blog. Holding two drinks. Calm. Cool. As unreadable as ever .

He walked up beside Rob and handed him a glass. Then turned to me.

“Diana,” he said with a nod.

I blinked. “Hi.”

Rob looked between us. “You two know each other?”

“Professional context,” Nate said smoothly.

That was it. No smile. No wink. No explanation.

I turned to Rob. “Well, congrats. You have excellent taste.”

Rob smiled. “Don’t I?”

They drifted off a moment later, and I stood frozen in place, still holding my untouched wine.

So.

Nate was gay.

Nate dated another super-hot guy.

I stared after them.

No hand-holding. No overt affection. But Rob had said “date,” and Nate hadn’t denied it. Hadn’t said a word.

Poker face, as always.

I took a long sip of my wine then muttered to myself, “Well. That settles that.”

It didn’t.

Not even close.

***

A few minutes later, I spotted Brad. Walking through the crowd like it parted for him.

Navy sport coat, white shirt, easy confidence.

Like he belonged here—or anywhere. He caught my eye, smiled, and raised his glass in a kind of there you are moment that would've been swoony if my internal monologue hadn’t just short-circuited ten minutes earlier .

“Sorry I’m late,” he said when he reached me. “Didn’t know valet was a whole situation.”

“Don’t worry,” I replied. “You missed the part where I accidentally hit on someone’s boyfriend.”

He chuckled, clearly thinking I was joking. “This place is wild.”

He touched the small of my back lightly as we moved through the room, and I could feel it: Nate watching. His gaze tracked us like it was passive, like it didn’t matter, like he wasn’t reading every micro-interaction and filing it away for some eventual report.

I smiled too hard. Laughed a little too loud. Steered Brad toward the photobooth just so I wouldn’t have to see Nate’s face. Brad hesitated—just for a second.

Then: “Let’s circle back. Lighting’s weird right now.”

He said it casually, but he’d already turned us toward the bar.

Fine. Maybe he hated bad lighting. Or couple shots. Or looking documented.

We turned a corner near the bar, and there he was again.

Nate.

Standing beside Rob, still holding a drink, still in that infuriatingly neutral charcoal button-up, still looking like someone had programmed him for maximum restraint and minimum reaction.

We made eye contact.

He didn’t blink.

I did.

“Diana,” he said, with a nod so professional it made me want to throw a canapé at his chest .

“Nate,” I said, aiming for breezy and landing somewhere near strained cocktail waitress on her third double shift .

“This must be Brad,” he said, turning with smooth precision.

Brad extended a hand. “That’s me.”

They shook—too long, too firmly—like two men pretending not to be measuring each other’s threat levels in calories burned.

“Nice to meet you,” Nate said, all smooth civility.

“I’ve heard a lot about you,” Brad added with an easy smile.

Nate’s expression didn’t change, but something flickered in his eyes—a calculation? Appraisal? Appreciation?

Oh God. Nate was checking Brad out.

That explained everything. Of course.

Hot guy shows up, Nate goes into quiet gay meltdown. Very relatable.

I briefly considered the odds that Brad was bi and instantly regretted everything.

Please stay straight, I thought. Just for tonight.

“Oh,” I cut in quickly. “Just the occasional warning label.”

Nate smirked, but it was subtle. Professional.

Rob smiled at me from Nate’s side, oblivious and lovely. “You look great tonight, Diana.”

“Thanks,” I said. “You too. Love your tie.”

It was the kind of compliment you give when you're trying not to imagine your matchmaker potentially flirting with your date.

There was a pause. Just long enough for all my insecurities to hold hands .

Brad, still charming, salvaged the silence. “We were going to try the Scorpio cocktail. Diana’s making me order the dangerous one.”

Nate raised an eyebrow. “Photobooth didn’t make the cut?”

Brad smiled. “Maybe after a few drinks. I’m camera shy.”

I blinked.

Camera shy? The man had a professional headshot on his dating profile, so airbrushed it could’ve passed for AI.

But sure.

Shyness. Lighting. Nothing to see here.

Nate just hummed—neutral, unreadable. “Smart move. Some of those hats are legally actionable.”

“I can pull off almost anything,” Brad said with an easy grin.

I did not like how Nate’s mouth twitched at that.

Rob, bless him, stepped in. “You two have fun. Don’t forget to try the cocktail. It might ruin your life, but in a good way.”

We murmured goodbyes and parted.

Half an hour later, I was midway through a very decent cocktail and nodding at Claudia—Senior Matchmaker, velvet dress, a mind like a scalpel—as she asked me polite questions about work.

Her eyes flicked across the room to Brad.

“Your date?” she asked lightly.

I nodded. “Brad.”

Her smile froze for a half-second. “Brad,” she echoed. “You know, I could swear I saw him on a dating app under another name a while back. Same photo. It was flagged, actually. ”

My brain short-circuited for half a beat. “Flagged?”

“Oh, nothing serious,” she said quickly, already smoothing it over. “Could’ve been a duplicate. People get creative with names sometimes.”

“Right,” I said, my smile staying in place like a hostage situation. “Of course.”

She looked at me a second longer than necessary. Then tapped her glass to mine. “Just be careful. Handsome ones always make the messiest client files.”

And with that, she drifted away, leaving me with a glass of wine, a slightly raised heart rate, and a date who was either perfect...or not Brad at all.