Alright mate,
Has this ever happened to you? (it's happened to me).
You had a good time on a date with a woman.
She seemed engaged, the conversation was flowing, and you left feeling excited about seeing her again.
And then she just didn't follow up.
No second date.
You're sitting there replaying the whole thing trying to figure out what you did wrong.
If so, let me explain what I think is really going on…
You were probably perfectly pleasant company.
But you weren't memorable.
And the reason you weren't memorable isn't because you're a boring person.
It's because Nice Guy Syndrome causes you to edit yourself until what leaves your mouth is safe, flat and forgettable.
And the sad truth is, you do this because at some point you were taught that your authentic self needs to stay hidden … or else.
Maybe you were bullied or humiliated. Maybe home was a place where it was safer to shrink.
Either way, your mouth-filter got set too high.
And now you can't just let yourself relax and be spontaneous.
Is this too much? Will this land wrong? What will she think if I say that?
(You might not notice these thoughts appearing. You might just notice your body freeze up and you can't "get your words out").
The good news is you don't have to wait until you've done years of inner work before this changes.
There's a framework I use in my coaching called the three levels of communication.
Each level goes deeper than the previous, and once you start using this, you can begin leaving a lasting impression on people.
(This is what makes the difference between a woman who can't stop thinking about you and one who forgets you the moment she gets home).
Level 1: Informational
Let's say you're on a date talking about your vacation to Egypt.
You might say:
"I went to Egypt for seven days." "I was in Cairo." "I flew with Ryanair."
It's fine and necessary sometimes.
But sharing just information is just not interesting.
And here's the problem.
This is where most Nice Guys and People Pleasers stay. And they have no idea.
(until I point it out to them).
So I invite you to think of your last conversation.
How much of it was just you sharing information?
Level 2: Personal
The next level down is personal.
This involves you sharing your actual feelings about the thing.
"I went to Egypt and honestly didn't enjoy it that much. Too hot, too overwhelming, people were aggressive trying to sell me things in Cairo and I just felt completely overstimulated."
Already you're revealing something real about yourself.
Already you're more interesting.
And you didn't have to be alpha, witty or charming.
You just had to drop the filter and be more authentic.
But there's a final layer of communication.
It's scary but I promise you if you start to go here, this has the power to dramatically transform your relationships and experiences with women and beyond.
Level 3: Relational
This is raw, present moment honesty about your experience in the here-and-now.
"Actually, I'm feeling a bit embarrassed about sharing the story about Egypt with you. I'm afraid that you'll think I'm not a fun person."
Or, if I may give you a live example directly from me right now as I sit here typing this…
I feel a little insecure that you won't find this email interesting.
(this is true)
Now let me ask you, how did that impact you just reading that raw honesty from me?
Did you feel more connected to me or less? Was it boring?
Compare it with a line I could throw in from Chat GPT or something and you might get what I'm saying.
This is the level that makes you unforgettable.
But when you start flowing between all three levels naturally, something interesting happens.
You don't just become a better conversationalist.
You start shifting the belief that if people see the real you, they'll reject it.
Which is how the toxic shame that sits at the root actually starts to resolve.
Authentic communication like this is one of the five pillars inside Pleaser to Leader, my 12-week 1:1 coaching programme.
We work on it as a live skill, practised in real situations, alongside the deeper identity work that makes it stick rather than just being something you logically understand but can't seem to change.
If that sounds like what you need, you can apply for a spot below. I only have 2 spots available this month.
Stay courageous.
Oliver
