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What Dating Apps Taught Me About My Own Process

Finding enough clarity to wrap up my personal experiment

Stay Curious · August 27, 2026 · 10:40 PM EDT · 3 min read

Prefer listening? Listen to the podcast episode here.

When I first started experimenting with dating apps, I thought the problem was the people. Then I thought the problem was the app.

That’s what frustration tends to do. When something isn’t working the way you expect, it’s easy to look for someone or something to blame.

But the more experience I had, the less those explanations made sense. I started noticing patterns instead.

Certain behaviors kept showing up. Not just from individual people, but across different conversations. I started wondering whether the environment itself was producing those behaviors.

Eventually, I stopped looking for a bad guy. There isn’t one.

People are responding to the environment in ways that make sense within that environment. The problem is that what makes sense for the environment doesn’t necessarily work for me.

Phase 1 vs. Phase 2

Looking at my own behavior, I noticed two distinct phases in how I approach someone on the app:

  • Phase 1 (The Profile): Evaluation. I look at pictures, skim the prompts, and make a quick judgment call on whether to connect.

  • Phase 2 (The Match): Exploration. From there, I naturally want to be curious, ask questions, and explore who the person is.

What I ran into, though, was that the people I matched with often seemed to keep the evaluation going into the chat.

The result was what I started thinking of as trading bios: I offer a fact to be weighed, they offer a fact to be weighed, and nobody really picks up a thread to explore.

If you’re talking to multiple people at once, I can see why that approach might make sense. It just doesn’t work for me.

Testing the Pattern

Once I noticed the pattern, I tested it in real time.

Whenever I tried to jump straight into exploring and being curious, the conversation usually hit a wall. But as soon as I shifted gears and gave them something simple to evaluate, the back-and-forth picked right up.

That was the part that finally made everything click.

The evaluation phase doesn’t necessarily end after the match. I’ve experienced it in messages, on phone calls, and even in person.

At some point, I realized I wasn’t waiting for the evaluation to turn into exploration anymore. It was the interaction.

And staying in that mode too long is exactly what kills my interest.

Wrapping Up the Experiment

This isn’t a grand takeaway about dating apps as a whole, and I’m not claiming to have solved anything universal. I simply learned enough to understand what was bothering me.

At first, I thought people were the problem. Then I thought the app was the problem. Now I think the environment simply produces behaviors that make sense within it.

There is no bad guy. I just don’t like what the environment asks me to do.

I kept coming back because I couldn’t explain that feeling. Now I can. That’s enough for me to wrap up the experiment and move on.

Bonus: The Song Swap

As a lighthearted change of pace while I was still trying things out, I asked a few matches to share a song that matched their mood that day, and I sent one back in return.