The easiest way to approach a woman

Alright, mate.

It’s been a while.

I’ve just come back from a few weeks in Portugal with family.

Hot sun, lots of peri peri chicken, and a few extra kilos gained. Worth it.

Now that I’m back in Lisbon, I’ve been reflecting on a huge topic for men like us: dating as a recovering Nice Guy.

I love shadow work and healing, but I also believe in pairing the inner work with practical skills.

And one of the most essential skills?

Approaching women.

If a man can’t approach with confidence, his dating life feels out of control:

• He’ll settle for women he’s not excited about.

• He’ll go through long dry spells (hello Pornhub).

• He’ll feel the clock ticking as he gets older.

But approaching is scary.

Thoughts like “What if she thinks I’m creepy?” or “What if she rejects me hard?” can stop you before you even try.

That’s why I teach the Interest Test Approach.

It’s a simple 4-step process that makes approaching easier and more natural.

And here’s how it goes:

1. Get out of the house. Go to classes, parks, coffee shops. Just be around people. 90% of men don’t do this enough.

2. Audit your body language. Walk slower, stand tall, relax your face, half-smile, and make soft eye contact.

3. Test her interest. If you see a woman you like, hold her gaze a moment longer. Don’t stare. If she looks away sharply, move on. If she glances back 2–3 times or smiles, that’s your green light.

4. Approach. Don’t overcomplicate it. Walk over, hold eye contact, and say: “Hi, I’m [your name].” That’s all it takes.

I used this exact process last Saturday in the park. She passed the interest test, I approached, and now we’re going out for dinner tomorrow.

It really can be that simple.

You aren’t as unattractive as you think.

You probably just seem closed off.

When you open up, you stop feeling invisible and start being noticed by the kind of loyal, feminine woman you can actually build a healthy relationship with.

If you’re a single man over 30 and you’re ready to end toxic cycles and finally attract a loyal, feminine woman … book your free 30-minute call here.

(I only have space for one new client this month.)

Stay courageous,

Oliver