For the first stretch of my dating life, I asked questions for a bad reason. I wasn’t curious. I was buying time.

I’d tell a story that made me look good. Then the second I ran out of material, I’d turn a question on her so I could reload and think of the next thing to say about myself. Her answers were the gap where I caught my breath.

Then I read something that rewired it. A guy is on a plane next to a woman he finds attractive. The whole flight, he keeps asking her better and better questions. They talk for hours. He barely says a word about himself. And when they land, she tells him he’s one of the most interesting people she’s ever met.

He was interesting because he was interested. That was the whole trick, and it wasn’t a trick at all. I didn’t have to earn the conversation by performing. I could build the entire thing around understanding her.

What I started listening for

Once I stopped using questions as filler, I started listening for the overlap. Not the words. The demeanor.

I once asked a date about growing up in Iowa, and I could tell she didn’t want to go there. That was fine. It also told me something real, faster than an hour of small talk would have.

So on a date, I’d watch for three things:

• What lights her up. The topic she can’t wait to answer. The one that makes her smile before she’s even started.
• Whether the curiosity runs both ways. Does she get curious about the same things back, or is she just being polite?
• How much I was talking. I tried to do the minority of it, maybe 40 percent. More than that, and I’d slipped back into performing.

And the questions themselves aren’t a script. I never had a standard list. You riff off the person in front of you.

Two that worked for me. To someone who’d moved here from another country: “When you go back home, what food can you not wait to get that you can’t find here?” To someone playful: “If your life had a theme song, what would it be?”

Neither one is clever. Both open a door. Then you follow her through it instead of reaching for your next question. That’s the actual move. Ask, then get genuinely curious about the answer. The overlap shows up in there.

Worth your time

There’s a Harvard study on exactly this. Researchers found that asking more questions, and follow-up questions especially, made people more liked. In a speed-dating version, the question-askers were more likely to land a second date. It’s a short, plain read, and it backs up why the follow-up matters more than the opener.

[Asking Questions Increases Likability](https://www.psychologicalscience.org/news/minds-business/asking-questions-increases-likability.html)

From the channel

If you want the bigger frame behind this, my video on the six mindset shifts covers the Overlap itself. You’re not trying to impress everyone. You’re trying to find the handful of people you actually fit. Better questions are how you find them.)

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~Michael

Intentional Chemistry · intentional dating for men who want something real