Some years ago, I remember going out to dinner with a whole bunch of people I’d “met” on the Internet—I think on OK Cupid, if I recall correctly, which will tell you how long ago this was. One of my partners at the time, Shelly, accompanied me. She fancied one of the people due to be present…I don’t even recall who, though I think I have a photo of that meetup lost somewhere in the deep inner dungeon of my 300-gigabyte Photos archive.

After dinner, Shelly roundly criticized me. “Can’t you tone it down a bit when you meet someone?” she said. “You know, be a little less Franklin? I was trying to make a good impression!”

I think about that from time to time when I meet people. It’s an approach to dating and relationships I really don’t agree with—in fact, I’ll even go so far as to say it’s harmful. I thought about this again when I saw a question on Quora about dating, asking how many dates it takes before one stops feeling awkward. The correct answer, in my opinion, is zero.

This is a terrible approach to dating. (Image: engin akyurt)

Awkwardness, in my experience, invariably means there’s something unsaid that needs to be said. It’s a warning sign, a danger signal of inauthenticity. Authenticity is, if you want successful relationships, absolutely vital, and authenticity starts right from the beginning.

Awkwardness on a date, again in my experience, generally means two things:

  1. You’re trying to be on your best behavior; and
  2. You’re trying to avoid talking about certain subjects because you don’t want to venture into controversial subjects.

Both of those things are big, ugly, bad mistakes.

Yes, I know. Dating advice articles tell you to do both those things. Dating advice articles are shite.

Do not try to pretend to be something you aren’t. That only causes grief down the road. Every argument that ends with “it’s like I don’t even know you!” or “you just don’t see me!” starts with being inauthentic early on.

“Oh, Anakin, I just don’t understand you!”

This is an extremely important idea that I’m frankly surprised a lot of people don’t get. “I have to make a good impression because otherwise I’ll scare my date off!” If you are not bringing your true self to that first date, if you are inauthentic, if you are pretending to be someone you’re not, you’re wasting your time.

The purpose of a first date IS NOT to impress the other person. The purpose of a first date is to see if you’re compatible enough with each other to keep dating.

Do not try to avoid “controversial” topics. Again, you’re trying to gauge compatibility. It’s better to find out you have radically different beliefs as soon as possible.

People publish all kinds of “no go” conversational subjects on dating advice columns all the time. I think that’s dumb.

Things I’ve talked about on a first date:

  • Religion
  • Sex
  • Politics
  • Ethics
  • History
  • Social causes

Again, and I cannot emphasize this enough: You aren’t there to impress the other person. You’re there to see if the two of you are a good match, before you invest years of your life in a relationship. Be authentic. Talk about things that are important to you.

If you do that, there is no awkwardness. It’s a lot easier to be comfortable when you’re not busy pretending to be someone you’re not.

It also means you don’t need to keep up the act later. The more authentic you are from the very start, the more true you are to yourself, the less you have to stress about maintaining the façade. And honestly, who has time for that?

That’s true of life outside of dating, too, by the way. The more you show up as your authentic self, the less awkward you are in general.

Now, approaching someone with the goal of making an impression has its place. If you’re trying to land a new job or win a political nomination, authenticity is less valuable than people-pleasing. In your social and romantic life, though, if you try, like Shelly did, to impress others rather than to bring your true self to your social life, well, don’t be surprised when you find yourself in inauthentic relationships. If you’re concerned that bringing your true self to your social interactions might scare people off, then perhaps that points to something within yourself that could benefit from a bit of work.

Yes, showing up with your true self rather than showing people what you think they want to see means there might be times you don’t get to shag the person you want to shag. It happens. Take that as a feature, not a bug. Painful experience: shagging people who are not a good fit for you never ends well.

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