I'd like to start with a quick story about something I experienced when dating. This one starts at a coffee shop, with me sitting across from a woman I had texted with for weeks before finally asking her to meet in person.

We hugged, sat down with our coffee, and I hit a wall about ten minutes in.

I’d thought of a question to ask her. Then I remembered I’d already asked it over text, days earlier, and her answer had turned into a genuinely funny exchange. So instead of the question, I brought up the exchange. We both laughed. Then we stopped laughing, because we’d already wrung that one out.

I spent the rest of the evening hunting for something we definitely hadn’t covered.

It wasn’t a disaster. This happened more than once, and a few of them still turned into a second date. But I keep coming back to what I gave up by waiting to ask her out. We’d pre-spent some of the best parts of that first date. We spent them over text, where I never got to see her face while she was laughing. That was my loss.

Texting has one job

For a long time I had this backward. I thought a great text conversation was proof the date would go well, so I kept it going. The better it got, the less urgent it felt to move on to meeting in real life. Sometimes I talked myself right out of asking.

Texting has one job. It earns you a real conversation. That’s all it does.

It can’t build attraction, and it can’t tell you whether you actually fit. You can’t see the overlap in a text thread. Every extra day you ask texting to do those things costs you material you can’t get back.

That one took me many dates to understand, so I’ll say it again. The only job of the text conversation is to get you in front of her.

Two things changed once I believed that.

I stopped waiting for permission. Early on, I’d wait for a flirty signal from her, some sign that there was genuine interest in meeting. I was once in a good, easy text exchange with a woman who happened to be at a baseball game. The back-and-forth was friendly but not flirty. I was responsive but kept waiting for that signal so I could bring up coffee. She left me on read before the game ended. The ask was my job, not hers.

I started watching for the first opening. A funny moment, or something we both had going on. Not a rule about message counts. A decision to look for an opening and take the lead instead of waiting to be invited.

Then I made the offer easy to say "yes" to, and just as easy to answer with a "not yet":

Clear enough that she knows what I’m asking. Loose enough that she can answer with anything from “I’d love that too” to “that sounds fun, but I’d like to get to know you a bit more first.”

If the conversation kept rolling, I’d end the night with “no pressure, but the coffee offer definitely still stands.”

If she still wasn’t sure, that was information I could use. Asking that way made my intentions clear. Once I adopted this approach, more of my messaging conversations resulted in scheduled first dates. Even when it didn't, I knew it wasn't because she didn't know I was interested in meeting.

A standing offer. Clear about what I wanted. Cheap for her to turn down. And it didn’t expire.

Worth your time

Researchers surveyed 433 online daters, average age around 40. They looked at how much messaging happened before the first meeting, then at how that meeting went. The researchers concluded that there is a sweet spot of transitioning from messaging to a face-to-face meeting within 2 to 3 weeks.

Candidly, I would typically make the offer to meet in person within 1 or 2 days, with the face-to-face meeting taking place within a week. Some of the women I dated preferred things to move a little more slowly. That was fine with me- especially knowing that she was aware of my intentions.

The key is to recognize that there is a "window". A little messaging before you meet helps the date go well. But keep texting for too long, and the effect flips. As you approach the end of the window, the longer you wait to meet, the worse that first meeting tends to go.

Keep in mind that a long text run builds a version of the person that the real meeting then has to survive. Things will go much better if that version of you is based on real-life interactions.

​When Online Dating Partners Meet Offline. The research behind why you want to find the sweet spot.

From the channel

Taking the lead in offering and planning dates is habit #9 of the 11 dating habits I learned on my dating journey. If you'd like to learn more and hear about the other ten, here's the video for you: First Date Mistakes Men Make While Trying to Impress Her​

Michael

Intentional Chemistry · intentional dating for men who want something real