How To Never Have An Awkward First Date Again (Hint: It’s Not Me, It’s You)

A collection of psychological tips and tricks from someone who first dates like it’s their day-job

I don’t know at exactly what point it becomes obvious that one has entered the realm of serial first-dating, but — if I had to guess — I’d say nearing the count of 30 different first dates in less than 10 months would probably be cutting it pretty close…

So be it; I am a serial first-dater.

Perhaps you want to blame it on my propensity for experiencing spontaneous yet short-lived fascination with meeting new people, my seemingly insatiable desire to venture outside of my comfort zone, or just the very natural human desire to love and be loved.

You might be wondering what the hell is so alluring about spending an unspecified amount of often abysmal (and even more often — awkward) time with a complete stranger?

My answer is that it can be hard to say exactly, but that I believe it can be boiled down to a few key findings of my experience:

  1. That going on first dates is an unparalleled opportunity for self-improvement in areas such as interpersonal relationships, self-esteem, open-mindedness, agreeability, conversational skills, non-verbal communication, and the reduced perception of awkwardness.
  2. That the more time your spend talking and meeting strangers, the less strange this activity begins to feel. Routinely stepping outside of your comfort zone directly increases the circumference of said zone.
  3. That people can and will surprise you more often than you might think.

Instead of dissecting the reasoning behind these three points, however, I’m going to use them as a springboard to teach you how to never have an awkward first date again — Let’s begin!


“Awkwardness should be viewed as an opportunity to connect with another person on the mutual inability to conceive the norms of an interaction.”

— Adam Kotsko

The concept of awkwardness is one that describes the feeling of discomfort that occurs when we are in a state of emotional unfamiliarity. As human beings who exist in a society with a particular set of norms and acceptable behaviours, awkwardness is a feeling we experience when we realize we are unaware of — or, at least, unaware of how to obey — the norms of any given situation.

Naturally, in circumstances where we have familiarity, there is protection against the occurrence of awkward moments because we are already aware of the accepted (and not accepted) parameters of the interactions.

Think about it; the awkwardness of a first date doesn’t come from the greeting of either a handshake or a hug — it comes from not knowing which is going to be most acceptable, and (if you’re really unlucky) getting caught somewhere between both!

So, the trouble with norms is that they’re not exactly set in stone. They can differ immensely between different individuals, with any one person viewing the ‘right’ way to conduct themselves at any one moment, in complete contrast to the next.

First dates are a wonderful example of a more or less norm-less situation. For starters, both parties are only just meeting for the first time, with very little prior information available on what is to be expected of the other. This allows room for any number of potentially mis-aligned norms to contribute, not only to the experience of awkwardness, but also to the fear of the experience of awkwardness, in addition.

Secondly, keep in mind that dates, themselves, can vary so dramatically in their definition, that what one person deems a run-of-the-mill meet and greet might leave the other utterly bamboozled. Between these major uncertainties, as well as the added pressure of actually liking one another, going on a first date can be the perfect storm for awkwardness — if you let it, that is…

Awkward (It’s Not Me, It’s) You

Simply put, in order to solve the problem of awkwardness that arises when two people meet each other for the first time, we need to start by addressing the source of awkwardness that is you.

First and foremost, it can be vital to grasp the idea that an awkward moment becomes 50% less awkward the second you decide it isn’t that way to begin with. This is because awkwardness is something that’s felt internally, not externally, and largely happens in your head.

So, I don’t care if you’re on a date with Mr. McMajorlyAwkward, or not; as soon you stop feeling awkward about what’s going on, the sooner what’s going on stops being awkward (at least, for you)!

And why shouldn’t you feel awkward, you ask? Because there is literally no alternative way to navigate the current first-date situation than exactly what you’re doing right now.

In this sense, awkwardness doesn’t mean that you’re doing something wrong, it means that you’re paying attention to what you should be doing right — and that you just don’t have all the information quite yet.

The point here being, that awkwardness can totally make you feel uncomfortable if you let it — hell, it can make you want to shrink inside of yourself and practically die — but that’s a choice that you (and only you) really get to make.

So what if the person you’re on a date with is being completely awkward? You don’t have to join them in sweaty, silent solidarity, I can promise you that!

Awkward Us

The inherent awkwardness of you, the date itself, or the other individual, aside, there are some scientifically proven steps (also tried and tested by yours truly) that you can take in order to minimize the discomfort of both you and the other party:

  • being light-hearted/humorous about the awkwardness
  • talking about common interests
  • speaking positively about the other person
  • giving or receiving an offer of help
  • encouraging a comfortable silence

These techniques work so well, because they immediately dismiss the idea that you or the other person would be judged for your failure to perceive the norms of the situation. This is because each of these actions either:

  • A) establishes a norm, such as joking around with one another, engaging in comfortable silence (maybe by eating, drinking, or even people-watching), or giving/receiving help.


  • B) assures the other person that you’ll figure the norms out together, by speaking positively about them, or turning the subject of the conversation to one of mutual interest.

It makes sense that as soon as both parties realize that the other is not at risk of rejecting them, the awkwardness we’ve been evolutionarily hard-wired to feel, disappears, or — at the very least — significantly lessens.

All in all, there’s absolutely no reason we should let the fear of a little awkward dictate our dating lives (whether that’s as a serial first-dater or otherwise)…

“Instead, we should view these awkward interactions as an opening towards a more fully human mode of being-with each other.”

— Adam Kotsko

I’ll take it…

Anyone for a first date?

Alexandra Walker-Jones — March 2021

Writer and published author with an international background in psychology, nutrition, and creative writing. I’m just here to learn ;)

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