Getting your first Girlfriend – The Flirting

When it came to getting my first girlfriend, my initial attempts at flirting were a version of what I like to call “the performing clown.”

Some guys, when intimidated by women they?re attracted to, freeze, go quiet, and avoid any and all interaction with them. They find women threatening, so they react as if they?re threatened.

Other guys, like my teenage self, go in the opposite direction. When intimidated by women, they act in ways that seek their approval. Some guys will agree with everything they say, other guys will try to demonstrate their virtues, and a lot of guys will try as hard as they can to make them laugh.

And this last one? It?s a doozy. Because it kinda works and doesn?t work at the same time. Let me explain:

When I was younger and in my “performing clown” phase, I was pretty funny. I could make girls laugh, and that made many of them like me. As far as ?game? is concerned, that?s a good thing. I?d recommend it.

Where this went wrong is that it made me dependent on laughs to feel like I was “doing well”. If I wasn?t making a woman laugh, I didn?t know how to interact with them. This meant:

  • I never shut up
  • I never communicated my desire
  • I was super competitive with other “funny guys”
  • I never made a move (i.e. I never tried to kiss her)
  • I never formed genuine connections with women

In short, my relationships with women were entirely defined by a desire to be funny. I was just the guy who made them laugh. Beyond that, my relationships had no substance, and I certainly couldn?t act on any mutual feelings of attraction.

This sucked. And, like all things that sucked, it evolved.

“The performing clown” evolved into “funny guy who?s “cooler? than her”. This is another mask guys throw on to deal with their fear of women, and I kinda did as well.

Instead of trying to make her laugh all the time, I dished out many of the laughs, no matter how playful, at her expense. This, again, isn?t a great idea, because it’s addictive, kinda works, and becomes a hard habit to break.

Just as girls like to laugh, they also like a guy who can poke fun at them. This is a fairly normal human trait. If you have solid self-esteem, it?s fun to poke fun at your dumb mistakes and flaws, and when people do this, it can be a great way to build connection.

Where it sucks is when it becomes your ONLY form of expressing intimacy, which, when you?re attracted to women while simultaneously afraid of them, it rapidly does. This is rampant in Western cultures, especially the US and UK.

It also sucks because as your desire to poke fun at her and seem cooler than her stems from a toxic place (your fear of women), it will always end up coming across as mean spirited, and degrading. You essentially get by on insulting people.

A pretty lame and cowardly way to live.

But this is just one example of an evolution of bad flirting. There are countless others:

The quiet guy who ends up avoid women entirely.?The awkward, socially clumsy guy who ends up thinking all women are bitches and less than men. In my experience, there are dozens of permutations of this, and they stem from the same root cause:

You find women threatening, so you react to threatened feeling.

And when it comes to getting your first girlfriend, this is a HUGE obstacle.

So let?s see if we can help you solve it.

What is flirting?

The way to think about flirting is any playful or direct expression of your sexual interest. This can be anything from a wink to a comment. It can be a subtle innuendo, or it can be an outright statement of intent.

The idea is that unlike a CODE: RED level expression of sexual desire – such as kissing, foreplay, or sex – flirting is something that conveys your desire but within the confines of normal human interaction.

It can be thrown into conversation anytime, anywhere.

Except maybe a funeral or a Sunday church service.

Now, when you feel threatened by women (that they?ll reject you, insult you, or shame you), expressing any kind of desire, let alone even speaking to them can feel impossible. This is why before you even learn to flirt, you have to have a basic level of ability with conversation.

You don?t have to have Tony Stark levels of charisma. You just have to be able to be relatively comfortable speaking to people.?Before you even attempt to start working on your ability to flirt, it?s best to iron that one out first.

Once you?ve done that however, you can start to introduce elements of flirting into your conversations with women.

These can be innuendos, compliments, non-verbals, jokes/banter – anything. Each of these will express your desire in a way that is playful, fits in with the conversation, and helps to build attraction.

Which, when it comes down to it, is the sole purpose of flirting.

However, you can?t just jump straight into attraction.

The one thing every guy gets wrong about flirting

In my early twenties I was a party in Brazil when I went outside with my friends to get myself some fresh air. Near the entrance, there was an unbelievably attractive woman in a red dress who glanced at me as I walked out.

For a moment, she did nothing, but after my friends left and she walked over and introduced herself. She was even better looking up close.

The conversation went insanely well, maybe too well, and she was heavily laying on the eye contact. Everything about her and the situation said that she was attracted to me and that I was 100% ?gonna score?.

(Hey, I was 23 and horny when this happened? it was pretty much my sole motivator in life).

But despite this, something was eroding my attraction for her.

Sure, she was beautiful. And sure, her body was unbelievable. And sure, I?m a sucker for a girl in red. And yeah, everything was going so smoothly it seemed like I?d be an idiot not to make something happen. But?my gut said otherwise.

Everything was a little too easy. A little too predictable. Like she was acting exactly how I?d want her to act, saying exactly what I?d want to hear. I?d had girls hit on me before, but never like this. Conversations, especially flirting ones are always slightly awkward in some way because people get clumsy and nervous when they’re attracted to someone.

I didn?t like it. I thought maybe she was a hooker or something, which isn’t my thing, so I excused myself and left.

Despite how ?attractive? she was, I was uncomfortable. And because I was uncomfortable I could never actually be attracted to her.

And it?s lucky that I wasn?t, because the next day I found out she left with a guy later that night, took him to another part of the city, and he was robbed at gunpoint. Nobody at the party knew who the girl was.

While this is a dramatic example, it illustrates a huge point.

Before any form of attraction can be built, there has to be comfort.

This means two things:

  1. Flirt with girls YOU are actually comfortable around.
  2. Prioritize comfort first, however small, before your flirt.

Comfort is any form of connection that allows people to feel safe and accepted around you. This can?t (and shouldn?t) be faked, and consists of:

  • Mutual interests (tv shows, sports, experiences, etc.)
  • Energy levels (hyper, chill, competitive, etc.)
  • Empathy with each other (sharing and connecting over emotions).

Building comfort requires you to be open, honest, and actively interested in other people. In my experience, it always starts with you sharing something first – whether that?s an interest or an honest, vulnerable expression of an emotion.

It can be built through conversation, or it can be entirely built by a vibe in an instant (i.e. she just gets a good impression of you because you?re a legitimately good guy and not hiding anything).

Once it?s there, however small, you?ll have a foundation on which to build attraction.

How to start Flirting

As long as comfort is there, and you have basic conversational skills, talking is going to continue, and do so fairly effortlessly.

You both will relax and talk about whatever is introduced as a topic / whatever interests you.

If you?re attracted to her, this is where flirting comes in.

Now the first thing you need to understand is that this is not complicated.

It?s not a skill.

It?s not a technique.

It?s not complicated.

All you have to do is introduce, in any way, a playful notion that you are attracted to her. This isn?t the same as a direct, non-playful (but enjoyable way) like kissing, but will help lead the interaction towards that.

This expression of attraction can be anything and can come in varying degrees of strength.

  • Tell her she looks cute when she?s thinking
  • Make fun of her / tease her playfully if she messes something up
  • Banter/roleplay with her that you?re boyfriend and girlfriend, husband and wife and that you?re separating, etc.
  • Make sexual innuendos, i.e. if you?re talking about favorite brunch spots say ?you?ll love them, they have enormous sausages??
  • Playfully accuse her of being into you

The only rule is that it?s FUN and that it in some way conveys YOUR ATTRACTION.

That?s it.

Keep it simple, build comfort, start flirting, and your relationships with women will start heading towards what just might be your first girlfriend.

Check out next weeks article for how to handle the tricky but fun territory of dating.

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About John Matich John is a writer from the UK who splits his time between travelling the world and trying to find unconventional solutions to dating and personal development. You can find more from him at