Page 9 of Falling for My Matchmaker (The Matchmaker Files #1)

“I’m proud of you,” Nate said without warning.

It landed like a compliment and a trap.

That was the thing about these sessions lately—they’d started to feel less like coaching and more like emotional obstacle courses. Soft lighting, hard truths. Eucalyptus and existential dread.

I blinked. “You’re proud of me? For what?”

“For letting yourself be seen,” he said. “For not armoring up. For going on real dates instead of interrogations in disguise.”

“That’s...disturbingly kind,” I said. “Are you dying?”

He smiled. “No. But you’re making progress, and I thought you should hear it.”

I shifted in my seat, immediately uncomfortable with the compliment. “Okay, well, just to balance things out—Brad kissed me.”

Nate looked at me. “And?”

“And it was like kissing a well-designed app. Everything functioned. Nothing crashed. But there were no sparks.”

“No sparks,” he repeated.

“Not even static cling,” I said. “It was all very...mechanical. Like a kiss designed by HR.”

He didn’t laugh, which made it worse.

“So I’m guessing that’s bad?” I asked.

“Not necessarily,” he said, in full Professional Nate mode. “You’re out of practice. Sometimes chemistry isn’t instant. And sometimes your body doesn’t know it’s safe until it’s been safe for a while.”

I stared at him. “That’s incredibly reassuring. And also sounds like something you’d say right before I join a cult.”

He smiled. “It’s called nervous system regulation. Not indoctrination.”

“Sure,” I said. “But still. I’m not sure I want to go on a third date with someone who kisses like an onboarding tutorial.”

“You don’t have to. But if everything else feels promising, it might be worth exploring.”

I hesitated. “It’s just...the third date.”

Nate tilted his head. “What about it?”

“You know .”

He blinked.

“You know ,” I said again, dragging the words like a body across gravel.

Realization dawned. “Ah. The mythical third-date threshold.”

“Exactly. The implied invite. The social contract. The ‘we’re doing this or we’re not’ moment.”

Nate sat back. “You know you’re allowed to set boundaries, right?”

“Yes, but also no?” I said. “I never know if I’m being a prude or just not into the guy. It’s like my instincts are on a delay.”

“Well, that’s the work,” Nate said. “Learning the difference between don’t want to and not ready to —and learning how to say no without giving yourself a guilt trip.”

I frowned. “Easy for you to say. You’re—”

I stopped just in time.

He raised an eyebrow. “I’m...?”

I coughed. “Good at this.”

“Mmhmm.”

Silence stretched for a moment.

Then Nate said, “We could try something.”

I narrowed my eyes. “Define ‘something.’”

“A mock third date.”

My brain short-circuited. “What?”

“You set the boundary. I push a little. You say no. We see where it gets uncomfortable and why.”

I stared at him. “You want to pretend date me and then try something ?”

“Just enough to practice the edge,” he said calmly. “You stop it whenever. Total control. No pressure.”

I paused then nodded slowly. “You know what? Sure.”

Because it felt safe. Because he was my matchmaker. Because he was gay. Very, very gay.

Nate smiled, relaxed. “It’ll be safe. You can stop it the second it feels weird.”

I hesitated. “But what if it feels weird right away and I freeze or say something weird or panic and slap you?”

Nate looked at me like I had just failed a very simple pop quiz. “Then you say, ‘Nate, this feels weird. Please stop.’”

“Right. Easy.”

More silence.

I cleared my throat. “What if I cry?”

“You won’t.”

“But what if I do ?”

“Then I’ll hand you a tissue and say, ‘That was useful data.’”

I blinked. “God, you’re so clinical.”

He smirked. “That’s why I’m good at this.”

“And also why you’re definitely not the guy I’d sleep with on a third date.”

“Excellent. Boundaries already working.”

***

I wasn’t overthinking the mock third date.

I was preparing . Like a professional.

I’d already put on fresh sheets. Not because anything was going to happen—obviously—but because old sheets felt...emotionally stale. You can’t confront your intimacy issues on wrinkled jersey cotton.

I’d shaved my legs. Again, not because I was expecting anything. But smooth skin made me feel grounded. Confident. Slippery with intention.

And yes, I’d chosen the black lace underwear.

It was comfortable. I’m allowed to have standards. Sexy and functional. Like a high-performance sports bra with trust issues.

“Are you seriously putting on matching lingerie for a fake date?” Lauren asked from the doorway, one eyebrow in a near-vertical climb.

“It’s not lingerie. It’s...underwar.”

She walked in. “Underwar?”

“Underwear,” I corrected, grabbing a pillowcase. “But battle-ready.”

Lauren flopped onto my bed, narrowly avoiding the pile of backup outfits I’d rejected already.

“Let me get this straight,” she said. “You’re doing full glam, fresh sheets, perfume I recognize from your ex’s birthday dinner— and you checked your condom drawer.”

I froze mid-spritz. “That was just to make sure I’m responsibly stocked. In case I need it for Brad. Later.”

“Oh right,” she said, dragging out the “right” like it was on trial. “Because Brad, who you’ve now kissed exactly once and described as ‘technically acceptable,’ is coming to pick you up for a third date that he won’t tell you the plan for.”

“Yes,” I said. “It’s a surprise.”

Lauren raised both eyebrows. “And surprises always end in separate hotel rooms?”

“He’s picking me up at seven. I’m not hosting. It’s not that kind of third date.”

“But you still changed your sheets?”

“Because I respect myself. And housekeeping is self-care.”

She stared at me.

“What?” I said.

“You’re staging your apartment like someone’s going to sleep here,” she said. “But it’s not for Brad. And it’s definitely not not for Nate.”

“He is gay!” I threw a towel at her.

Lauren caught it with zero effort, because of course she did. “Bisexuals exist, babe.”

“This one doesn’t,” I snapped, already halfway into the closet like I was being chased by my own logic. “Nate is not attracted to me. Also, he’s dating someone . That guy Rob? Literal human wallpaper of masculine perfection? Nate brought him to the party. ”

Lauren shrugged. “You sure Rob wasn’t just another client?”

“Rob said ‘date.’ Nate didn’t deny it.” I sighed.

“Even if— if —he were attracted to me,” I continued, emerging with a backup top I had no intention of wearing, “he’s my matchmaker. Matchmakers don’t date their own clients. That’s, like, page one of the rulebook.”

“And yet,” she said, tilting her head meaningfully, “you’re rearranging your furniture like it’s foreplay.”

“It’s a mock third date,” I said. “It’s basically homework.”

Lauren grinned. “You never wore lace for homework.”

I groaned and collapsed onto the bed next to her.

We lay there for a moment, side by side.

Then Lauren said, “Whatever this is—the sheets, the underwear, the candles—it’s not just about practice. Something’s shifting. You know that, right?”

I didn’t answer.

Mostly because I wasn’t sure if she was wrong.

Also because I was deeply committed to pretending that if I stayed facedown long enough, I’d just pass through the mattress and be reborn as someone with emotional clarity and a less flammable dating history.