The Myth of the Perfect Match: Ep4 – The Game We Didn’t Know We Were Playing

The Myth of the Perfect Match: Ep4 – The Game We Didn’t Know We Were Playing

When you agree to radical honesty with someone who sees too much, you discover that the most dangerous lies are the ones you’ve been telling yourself.

The Sunday He Didn’t Show Up

I waited forty-three minutes before accepting that Theo wasn’t coming.

The coffee shop filled and emptied around me—couples arguing over weekend plans, students with laptops and determined expressions, elderly men reading newspapers with the patience of people who had nowhere else to be.

I’d prepared for our fourth Sunday meeting with the kind of strategic intensity I usually reserved for work presentations. Had my question ready—something about his relationship with his mother, calculated to be invasive enough to demonstrate the game’s progression but not so invasive as to seem desperate for information.

Instead, I sat alone, feeling foolish in a way I hadn’t experienced since high school.

My phone buzzed at 11:47 AM. A text: Emergency at work. Rain check?

No apology. No explanation of what kind of emergency. No suggestion for when this rain check might occur.

I stared at the message, anger rising. Not just at being stood up, but at how quickly I’d allowed this person back into my life. How easily I’d convinced myself that our strange experiment was different from the usual games people play.

I typed three different responses. Deleted them all. Finally sent: Sure.

Then I went home and spent the rest of Sunday furious at myself for caring more than I’d intended to.

The Call That Changes Nothing

He called Tuesday evening while I was making dinner. I let it go to voicemail, then played the message while stirring pasta that suddenly tasted like cardboard.

“Claire, I know you’re probably… well, I know Sunday was unprofessional. Can we talk?”

I called him back immediately, hating myself for the eagerness in my dialing fingers.

“You said it was an emergency,” I said without preamble.

“It was. Is. My ex-wife called.”

The words hit differently than I expected. Not jealousy, exactly, but something more complicated. A reminder that he had a whole history I wasn’t part of. Stories that didn’t include me.

“I thought she was dead,” I said, remembering his earlier explanation.

“Not dead. Just… absent. She’s been living in Somewhere for two years. Working on a farm, apparently. Growing relationships .” He laughed, but it sounded hollow. “Very unlike the woman I married.”

“And she called because?”

“She wants to finalize our divorce. Officially. We’ve been separated but never… completed the process.” A pause. “She’s engaged to someone else.”

I processed this information, trying to understand why it required missing our meeting. Why it felt like an emergency worthy of disrupting our carefully established routine.

“Congratulations?” I offered, uncertain of the appropriate response.

“The point is,” he continued, “it made me realize something about our arrangement. Our game.”

Something in his tone made me put down my fork.

“Which is?”

“I think I’ve been using it as a way to avoid dealing with the fact that I’m not actually available for authentic connection. Not really. Not yet.”

The honesty was brutal and unexpected. I’d prepared for many things in this conversation, but not for him to dismantle the entire premise of what we’d been doing.

“So you want to stop,” I said. Not a question.

“I want to pause,” he corrected. “Until I can figure out why the idea of my ex-wife marrying someone else made me realize I’ve been treating you like a interesting distraction rather than a actual person.”

The words landed like small stones in still water. Creating ripples I couldn’t control.

“Is that what I am?” I asked quietly. “A distraction?”

“I don’t know,” he said, and the honesty was somehow worse than a lie would have been. “I thought I was ready for this kind of honesty. For whatever this is. But sitting in that lawyer’s office, signing papers to end a marriage that’s been over for years… I realized I have no idea what I want. From you. From anyone.”

The Question I Shouldn’t Ask

We met the following Sunday, but not at the coffee shop. At his suggestion, we walked through Prospect Park instead—moving targets are harder to pin down, harder to study with the kind of intensity our usual conversations required.

“Can I ask you something?” I said as we passed a group of children feeding ducks at the pond.

“Isn’t that the point?”

“This feels different.” I stopped walking, forcing him to face me. “Why did signing divorce papers make you question what we’re doing?”

He looked at me for a long moment, his expression unreadable.

“Because I realized I’ve been treating our honesty experiment like research,” he said finally. “Like I was collecting data about what authentic connection might feel like without actually risking it myself.”

“And now?”

“Now I think maybe I’m incapable of authentic connection. Maybe the reason my marriage failed wasn’t because we weren’t honest enough with each other. Maybe it’s because I’m fundamentally broken in some way that makes real intimacy impossible.”

The confession was raw enough that I felt exposed just hearing it.

“Do you want me to reassure you that you’re not broken?” I asked.

“Do you want to?”

I considered this question seriously. The old me would have rushed to offer comfort, to smooth over his discomfort with gentle lies and encouraging words.

“No,” I said instead. “I want to know if you think I’m broken too.”

The question surprised us both.

“What do you mean?”

“I mean, I’ve been sitting across from you for weeks, telling you truths I’ve never told anyone, and I still don’t know if I’m doing it because I trust you or because I’m desperate to be seen by someone who pays attention.” I started walking again, needing movement to continue this line of honesty. “I’m not sure there’s a difference.”

“Does it matter?” he asked, falling into step beside me.

“It matters if we’re both just using each other to feel less alone without actually risking anything real.”

We walked in silence for several minutes, passing joggers and dog walkers and couples having their own complicated conversations on park benches.

“Your turn,” I said eventually. “Ask me something dangerous.”

“Are you in love with me, or are you in love with being understood?”

The question stopped me again. Not because it was cruel, but because it cut to something I’d been avoiding thinking about too carefully.

“I don’t know,” I admitted. “How do you tell the difference?”

“I have no idea,” he said. “That’s the problem.”

The Realization We Both Resist

“Maybe,” I said as we reached the park’s edge, “we need to add a new rule to the game.”

“Which is?”

“We have to try dating other people.”

The words felt strange coming out of my mouth. Like suggesting we set our comfortable house on fire to see if anything worth saving survived the flames.

“While continuing our Sunday meetings?” he asked.

“Especially while continuing our Sunday meetings. We tell each other about the dates. About how they go. About what we notice about ourselves when we’re with people who don’t know us the way we know each other.”

I could see him processing this suggestion, working through its implications.

“That’s…” he started, then stopped.

“Terrifying?” I supplied.

“I was going to say brilliant. But terrifying works too.”

“It would answer your question about whether we’re broken,” I pointed out. “If we can’t connect authentically with anyone else, maybe the problem isn’t us individually. Maybe it’s this weird hothouse environment we’ve created.”

“And if we can connect with other people?”

“Then we’ll know our honesty experiment worked. We’ll know we learned something about authentic connection that we can take into real relationships.”

“With people who aren’t each other.”

“With people who aren’t each other,” I confirmed.

We’d reached the subway entrance. The natural end of our walk, the point where we usually parted ways with plans for the following Sunday.

“So we’re really doing this?” he asked. “Dating other people while dissecting our experiences with each other?”

“Unless you have a better way to figure out what we’re actually doing here.”

He smiled then, the first genuine smile I’d seen from him all day.

“You know what’s funny?” he said.

“What?”

“A month ago, if someone had suggested I start dating again while conducting weekly honesty sessions with another woman, I would have thought they were insane.”

“And now?”

“Now it seems like the only sane response to an completely insane situation.”

I laughed, surprised by the lightness I felt despite the complexity of what we’d just agreed to.

“Same time next week?” I asked.

“Same time next week,” he confirmed. “But bring stories.”

As I descended into the subway, I found myself wondering if we’d just saved our strange experiment or completely destroyed it.

Either way, I realized, next Sunday was going to be very interesting.

The Dates Begin

I downloaded three dating apps that Tuesday. Not because I was particularly eager to meet someone new, but because the scientific part of me was curious about what dating would feel like now that I’d spent a month practicing radical honesty with someone who saw through all my usual strategies.

My first date was Thursday night. David, thirty-four, investment banker, photos that suggested he spent significant time at the gym and significant money on his clothes.

We met at a wine bar in SoHo—his choice, which immediately told me he was someone who needed to impress before he bothered to connect.

“So,” he said after we’d ordered, “tell me about yourself.”

It was such a standard opening that I almost laughed. After weeks of Theo’s laser-focused questions about my deepest fears and hidden desires, “tell me about yourself” felt like being asked to perform a children’s song at a concert hall.

“What would you like to know?” I replied, genuinely curious about what he’d ask for.

“The usual. What you do, where you’re from, what you’re looking for.”

The usual. As though human connection could be reduced to a standard set of data points.

I gave him the standard answers—the ones I’d perfected years ago, the ones designed to make me seem interesting without being challenging. Professional but not intimidating. Successful but not threatening.

He seemed satisfied with these responses, which told me everything I needed to know about David.

“My turn,” I said when he’d finished cataloging his own achievements. “What’s the most honest thing you’ve said to someone in the past month?”

The question clearly caught him off guard.

“Honest?” he repeated, as though I’d asked him something in a foreign language.

“You know. Truthful. Authentic. Something that revealed who you actually are rather than who you think you should be.”

He thought for several minutes, his expression growing increasingly uncomfortable.

“I guess… I told my mother I was disappointed she couldn’t make it to my birthday dinner?”

It was such a safe, small truth that I felt almost sad for him.

“And what’s the most honest thing someone has said to you?” I pressed.

“Why are you asking such heavy questions?” he asked, forcing a laugh. “This is supposed to be fun.”

And there it was. The difference between someone who wanted to know me and someone who wanted to have a pleasant evening with an attractive woman who wouldn’t complicate his life.

I made it through dinner, but barely. Every minute felt like wearing clothes that no longer fit—constrictive, uncomfortable, wrong.

When he texted the next day asking about a second date, I stared at the message for ten minutes before responding: Thanks, but I don’t think we’re looking for the same thing.

He wrote back immediately: What are you looking for?

I started to type the careful, diplomatic response I’d always given in situations like this. Something about timing and connection and hoping he found what he was looking for.

Instead, I wrote: Someone who asks better questions.

Then I blocked his number before I could lose my nerve.

The Sunday Report

“How did it go?” Theo asked the moment I sat down at our usual table.

“Terrible,” I said without hesitation. “Completely, utterly terrible.”

“Tell me everything.”

So I did. I told him about David’s predictable questions and safe responses. About how performing my old dating persona had felt like wearing a costume that no longer fit. About how I’d ended the evening feeling more alone than I had before it started.

“And you?” I asked when I’d finished. “Please tell me your date was better than mine.”

His expression suggested otherwise.

“Her name was Sarah. Twenty-eight, works in marketing, seemed intelligent from her profile.” He shook his head. “But the entire evening felt like we were reading from a script. She asked about my work, I asked about hers. She told me about her favorite restaurants, I told her about mine. It was perfectly pleasant and completely meaningless.”

“Did you try asking her anything real?”

“I tried. Asked her what she was afraid of. She laughed and said spiders and horror movies.” He looked out the window. “When I pressed for something deeper, she said I was being too intense for a first date.”

“Were you?”

“Probably. But here’s the thing—I couldn’t figure out how to have a surface-level conversation anymore. It felt like speaking a language I’d forgotten how to use.”

We sat in the strange silence of two people who’d accidentally learned something they weren’t sure they wanted to know.

“So what does this mean?” I asked finally.

“I think,” he said slowly, “it means we’ve ruined ourselves for normal dating.”

“Is that good or bad?”

“I have no idea.”

The honesty of his uncertainty felt more intimate than any declaration of love could have.

“Should we keep trying?” I asked. “More dates, I mean.”

“Do you want to?”

I considered this question seriously. The thought of another evening like the one with David made me want to delete every dating app on my phone.

“I want to understand what we’ve done to ourselves,” I said finally. “Whether we’ve learned something valuable about connection or just made ourselves impossible to please.”

“More experiments, then.”

“More experiments,” I agreed.

But as we parted ways that Sunday, I found myself wondering if the real experiment wasn’t the dates we were having with other people.

It was these conversations afterward—these moments of complete honesty about our failures to connect elsewhere.And what that might mean for whatever was happening between us.

To be continued in “The Myth of the Perfect Match: Ep5 – When the Experiment Becomes the Reality” – where dating other people reveals uncomfortable truths, the safety of Sunday conversations becomes addictive, and the line between research and relationship disappears entirely.

This was “The Myth of the Perfect Match: Ep4 – The Game We Didn’t Know We Were Playing”.
See also: “The Myth of the Perfect Match: Ep3 – The Game of Truth” where this dangerous experiment in honesty first began.

For insights into how radical honesty changes your relationship patterns, read “The Authenticity Trap: When Being Real Makes Dating Impossible” where I explore what happens when you can no longer tolerate surface-level connection.