It started with a Facebook message—a friend of a friend knew me, we both lived in New York, etc., so she decided to reach out. I assume her decision to do so was partially because my profile picture at the time made me look prettier than I am in real life.

This led to an exchange wherein phone numbers were exchanged and an agreement to hang out in the near future was struck. This came with the caveat that it wouldn’t too soon, on account of the fact I was heading home for the week for my older brother’s wedding.

We commenced texting rather regularly while I was home and in the week after I returned to New York. We were still unable to get together because she lived outside the city and babysat most weekends.

We’d spend nights texting back and forth while I was out with friends and she was taking care of children. I would show her Facebook photos to dudes who were suitably impressed. (Full disclosure: I showed my mom a picture of this woman and she expressed surprise that somebody so good looking would be physically interested in me.) They would ask me what we were doing, and I would say that we were “talking.” (A definition of “talking” can be found here.)

I didn’t understand why most found it bizarre that we were getting to know each other so well before actually meeting in real life. I figured that the more I knew about a person going into things, the better our meeting would be. I reasoned that I am much better on paper (or in most cases, on screen), and that it would be excellent for me to attempt to charm this lady through messages. So that when we did meet she wouldn’t think I was some extremely shy, sweaty weirdo.

But I soon found out why this approach is often not the best one. I was willingly and actively participating in something that has been coined “premature escalation,” according to this wonderfully informative story on the topic I read in the New York Post—like two months too late. In the story, Annie Daly wrote that it’s become more or less commonplace for guys and girls to engage in pre-date texting sessions, and that doing so can foster a false sense of intimacy that can ultimately set a person up for disappointment.

When we finally met at a bar called The Tippler, things started out well enough. We hugged and gushed about how nice it was to finally be able to meet each other IN REAL LIFE.

Then things got weird.

First dates are inherently awkward. I thought that by diligently getting to know this woman before we went on our first date, this awkwardness would be avoided. Instead, it was compounded.

We technically already knew each other, but not in the comfortable way that friends-turned-lovers do on their first dates.

In a few words: we were meeting for the first time, but we already knew each other.

We knew about each other’s jobs, families, lives, hobbies, etc.

So what else do you talk about?

We spent an hour or so regurgitating things we already knew about the other, and then elaborating on them to a point that was way too in-depth and uninteresting for a first date. (You probably shouldn’t be talking about an hour-to-hour breakdown of a person’s typical workday less than one hour after you have first laid eyes on them.)

To put it bluntly, the date wasn’t that great, and I don’t believe that either of us really enjoyed it.

But we’d already put so much time into it. It wasn’t like we had messaged a couple times on OkCupid and almost immediately decided to meet up. We had been talking rather regularly for a matter of weeks. There was too much of an investment for us to just let it go. So we got drunk and soldiered through. We kissed goodnight. We decided to go on another date, despite it being readily apparent that the two of us were not at all compatible in a romantic way.

One thing led to another and things did not get better. I became more busy at work and less inclined to spend my free time trying to make something work that I’d had high hopes for than more inclined to do, well, anything except that.

She eventually called things off, saying that we never saw each other and only ever texted. It had come full circle.

A month or so later I met a woman on OkCupid and we decided to go out. We’d exchanged pleasantries and like two messages back and forth before making plans to meet at a bar in Brooklyn.

We got our first drinks and sat down. One of the first things she told me was that after we started messaging she decided to stop looking at my profile.

“I like to kind of wipe the slate clean before I meet the person, so we’re like, you know, actually meeting when we meet,” she said.

She is a wise woman, and I have since adopted her standpoint vis-à-vis premature escalation. We had a decent date, but nothing that would have shattered the earth. I knew she wouldn’t be a girl I would see in the long term, and she knew that I couldn’t compete with her ex-boyfriend who had just moved to our neighborhood.

We only went on one date before going out separate romantic ways, but we’re friends now. Sometimes we text each other pleasantries and jokes. We’ll probably stay in touch for years now.

As for the first girl I mentioned?

I haven’t heard from her in months.