Conversation Skills
For Men

Are You Struggling to Approach Women?

June 26, 2023
▪ 4 mins read

Avoid falling into the trap of trying to make your approach "perfect"

If you’re struggling to approach women IRL you could be making the fatal error of trying too hard to make your approach "perfect".

When you focus too much on what’s the "right" or "best" opener, 99% of the time you will get so caught up (okay, worried) about having the perfect line that you will struggle to approach her. 

Compounded over weeks, months and years, this will simply then turn into you consistently psyching yourself out of saying hello to a woman you’re attracted to. This then creates a habit where instead of approaching a woman that you like, you will actually create a habit of overthinking, and not taking any action.

Soon this will turn into a belief that you can’t approach women because you can’t think of anything to say. 

So let me just set the record straight: There is no "perfect" opening line. 

When you’re getting started at approaching women, what’s far more important than having a perfect line; is getting into the habit of saying something and then gaining experience of how to handle the conversation that follows, which could go in many different directions. 

Women aren’t like a magic door, where if you say, "abracadabra" boom you’re in! 

Deciding is a process, and one that certainly doesn’t all hinge on the first words you say. 

She’ll decide whether she wants to keep interacting with you depending on her personal circumstances (is she single, and looking?), how you initially present yourself (are you her usual type?) and how the conversation flows, what does she learn about you? 

(Also I should remind you here that the decision making process also isn’t one directional, just because you’re attracted to her, shouldn’t mean you want to date her. 

To be more attractive, and to build your self esteem with dating you need to get far better at cultivating standards for yourself as a man. You can get my workbook on how to do this here

The point is: If you over think your first words to her too much, you’ll never gain experience of how to handle these other stages of the interaction: What do you say after your opening line? How do you handle it if she seems disinterested? Or VERY interested? 

Because of this, when I coach men on my coaching programmes like Academy, we focus first on getting you comfortable with actually approaching women, and after that we focus on finessing what you’re actually saying.

In that order: Condition yourself to approach first, make it smooth later!

As Voltaire wisely said, "Don’t let the perfect be the enemy of the good."

So if you want to stop struggling to approach women, what are some simple and easy ways you can start a conversation?

Step 1: Just say hi!

Now before you think, "that will never work!" have you actually tried? I’ve watched many men over the years trying this out, and the results can be surprisingly good. 

For a beginner it just gets the interaction started, and you may be surprised that when you’re finally in an interaction that you do manage to say something else to follow this up with! 

More advanced guys will sometimes choose to continually use this as their "go-to" opener as it gives them a sense of ease and presence, and keeps the conversation very open for her contribution. 

Yes, some women will also want to help drive the conversation forwards. 

Step 2: Use a simple, direct opener.

Direct openers communicate that you’re physically attracted to her, to some extent. Obviously avoid any direct references to her physical appearance that could make her feel uncomfortable, but you could try saying...

"I just wanted to / had to come and say hi..." (This implies the reason you’ve started this conversation is because you were attracted to her.) 

"I just wanted to say you look nice today." (Yes bland, but unlikely to cause offence.) 

Communicating some attraction right off the bat can be helpful for guys who find expressing any attraction to women incredibly awkward.

Again, you can refine how you express the interaction, both in terms of what words you use and when in the interaction you bring it up; after you’ve gained some experience and find the process overall less daunting. 

Step 3: Practising in "low hanging fruit" environments 

Most people will feel far more confident approaching someone they don’t know when there’s some context: Maybe you’re both part of the same club, it’s a singles’ night, you’re at a friend’s party. 

YouTube pick up artists will glamorise approaching women in no-context environments like the street: And yes you can meet women nearly anywhere, provided you’re conscientious about how you approach, but you don’t need to learn to do this. 

If you meet someone through a shared interest, or social group, they’ll be more likely to actually meet you for a date. 

So even if your end goal is to feel confident enough to approach women anywhere, you probably want to start practising in environments with lots of context: Build some experience there and then roll it out to more low-context approaches. 

The only exception to this, is if you have a good coach to help you get past the more challenging learning phase of meeting women anywhere. 

After spending 15 years coaching men (and women!) I know just how challenging it can be to self motivate, and how much benefit you can receive by having someone accelerate your learning when you’re just starting out. 

That’s why I’ve developed programmes like Academy, to be a comprehensive starting course to get you past struggling to approach women, and onto a totally new phase of your life where you can find dating fun, confidence building and rewarding.

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