Hey brother,
When I was in my mid-20s, I was dating a woman who was at university.
She was going to parties, meeting people, and spending time around other guys.
Meanwhile, I was struggling to build a personal training business and feeling pretty inadequate about myself.
Whenever I visited her, I felt anxious and jealous.
Who’s that guy? Have they got something going on? Am I bothering her? Is she losing interest?
But I had a rule in my head:
Don’t let her see that you’re insecure. You’ll push her away.
So I tried to act like James Bond.
Relaxed. Nonchalant. Completely unbothered.
Internally, I was a fucking mess.
And the harder I tried to appear confident, the more anxious I became.
I started stumbling over my words and overthinking answers to basic questions.
Eventually, halfway through a sentence, she stopped me.
“Oliver, can you please just tell me what’s going on with you? I can tell something’s bothering you.”
And even then, with an invitation to be honest, I froze.
“No, I’m alright. Let’s not talk about it.”
A complete lie.
That relationship eventually ended.
There was more to it than this, but my attempts to appear secure were actively making things worse.
I was so focused on controlling how she saw me that I couldn’t actually connect with her or feel comfortable in my own skin.
That’s what I call the female validation trap.
You’re afraid of losing her » You judge yourself for feeling afraid » Then you try to hide it, creating even more tension and insecurity » You lose her eventually
You can spend years doing this.
And I don’t want that for you.
So how do you start breaking free?
1. Notice how you chase reassurance
Checking your phone repeatedly or analysing her response times.
Checking her socials. Deliberately delaying your reply so you don’t appear too interested.
Ask yourself: What am I hoping this behaviour will make me feel?
Then practise slowing down before you act.
Give yourself a chance to notice the raw emotions, fears and feelings underneath the urge.
2. Learn to tolerate not knowing
No relationship can give you permanent certainty.
You can communicate honestly, treat a woman well, and still be rejected.
Your security can’t depend on “She definitely won’t leave.”
It has to become:
“I don’t know what’s going to happen, and I can handle not knowing right now.”
3. Pay attention to what her approval means to you
Does her attention mean “She likes me”?
Or does it mean “I’m finally good enough. I matter. I’m safe”?
For some men, this reaches back to growing up feeling that love had to be earned.
Start asking what you needed then, and how you can give yourself more of it now: encouragement, stability, acceptance, self-protection through boundaries.
A woman you met six weeks ago can’t be responsible for healing everything that came decades ago.
4. Stop shaming yourself for wanting to be wanted
You’re allowed to want affection, sex, intimacy, and reassurance.
You’re allowed to hope she likes you back.
There’s a huge difference between “I really want her to choose me” and “I need her to choose me so I can feel okay about myself.”
The goal is to enjoy her attention without making it the evidence of your worth.
5. Practise being direct
“I like you.”
“That bothered me.”
“I’m feeling insecure about this.”
“Something feels different. Can we talk about it?”
Being honest doesn’t guarantee the answer you want. But it gives you contact with reality.
And every time you express yourself honestly, you practise standing by yourself instead of hiding to manage someone else’s response.
6. Build a life that can withstand rejection
Friendships. Brotherhood. Meaningful work. Your health. Genuine interests. Standards for how you live.
These things deserve your attention because they make your life worth living.
One woman shouldn’t have to carry the entire burden of making you feel worthy, connected, and happy with your life.
For me, this is what freedom from female validation comes down to:
“I hope she chooses me. And if she doesn’t, I still choose myself.”
If you recognise yourself in this, it’s exactly the kind of work we do in my 12-week Pleaser to Leader coaching programme.
Together, we work on the patterns behind people-pleasing, overthinking, and losing yourself around women, so you can become more grounded, confident, and direct.
We’ll talk about where you’re at, what keeps getting in the way, and whether working together is a good fit.
Stay courageous,
Oliver
