Have you ever been on a date or in a relationship with one of those strong, hyper-independent, career-focused women?
If you're anything like me, you know how much of a test to our nice guy programming this can be.
A little while ago, I'm sat there waiting for Anna to arrive.
She's the CTO of a large software company.
And from her Hinge profile, I can tell she's the type of woman who knows exactly what she wants.
Two years ago, this would have intimidated the fuck out of me already.
It took a little back-and-forth when I insisted on making the plans (something I advise every man to do).
But ultimately she relaxed a little and let me take the lead.
She walks into the intimately lit cocktail bar.
Dark eyes. Wild curly hair. Gorgeous.
But as she sits down, she has that look of suspicion on her face.
The kind of look that says, “I’m here to figure you out.”
“Bring it on,” I think to myself.
Over the course of the date, the conversation goes from playful to serious. From shallow to deep.
She wants to know about some of my deepest traumas.
Fine by me.
I've done enough inner work that I'm no longer ashamed of the answers.
I ask her similar questions.
There are gaps in the conversation.
But I don't rush to fill them anymore.
I’ve become at peace with difficult emotions, so I can let the silence sit and enjoy looking at her without apologising for it.
And as time goes on, I’m noticing something.
It’s something that NEVER gets old.
She becomes more animated, laughing a lot. Giddy, even.
She scooches her chair around so she's sitting closer to me.
“Am I getting better with eye contact?” she asks playfully.
The woman who walked in looking ready to put me through my paces is melting before my eyes.
I feel ready for a change of scenery, so I suggest we leave.
We head to the bar to pay, where she protests that she wants to pay half.
I look into her eyes and smile, letting her know I'd like to treat her.
She smiles back before resting her head on my shoulder and her hands across my chest.
Some things don't need words.
I want you to know what's possible when you shed the nice guy programming.
This exact same date would have made me crumble just two years ago.
I was so deeply infected with nice guy syndrome that I would have spent the evening craving her approval.
I would have let her make all of the plans.
I would have nervously stumbled through her questions like I was at some job interview.
The anxiety and shame would have completely killed all sexual tension.
I would have felt like an anxious little boy in her presence.
Not anymore.
Remember this:
Your grounded, calming presence + your unapologetic leadership can be one of her biggest turn-ons.
Looks, money or status might get you on the date.
But it’s how she feels in your presence that makes the difference.
And if you genuinely feel at peace with who you really are and where you're going in life, she'll feel that.
Through men’s work, I’ve built relationships with amazing men who have my back which means I'm no longer terrified of rejection.
And I’ve created a life I so deeply enjoy that I’m genuinely indifferent to the outcome of one date.
She’s gorgeous. Of course I want it to go well.
But now I can enjoy the date without needing this to turn into anything.
That gives me the freedom to be myself.
According to Anna, she had never experienced a date like it.
I loved hearing that.
For me, it was a reminder of how far I’ve come.
If you recognise yourself in the man I used to be, this is exactly the kind of work we do in my men’s group and in my private 1:1 work.
Working through shame. Becoming emotionally grounded. Speaking with calm confident and magnetic truth. Building deep supportive relationships.
So we can stop chasing approval and start showing up fully .. in dating, relationships, and the rest of our lives.
For the group, we’re taking on just four new members, and applications close at the end of this week.
After that, we won’t open applications again until the end of October.
Want to join us?
Reply “GROUP” and let’s talk about whether it’s right for you.
Ollie
