One thing that isn’t often spoken about is how hard it is for men to approach women. It’s actually one of the hardest things we ever have to do and that’s the reason why the vast majority of us only ever do it while drunk and specially defined scenarios like a bar or a club. Well I don’t want to be that way anymore and have decided to get over this fear once and for all so to that end I’ll be approaching 2 women every day for 50 days and writing about what happens.

And just so we’re clear; this isn’t about ‘getting laid’; it’s about breaking through my personal limitations and learning to become a much stronger man. When a guy approaches a girl he doesn’t know, every one of his insecurities are shoved right into his face in technicolour HD and it’s in that moment that he really finds out what he’s made of.

It’s time to find out what I’m made of. Let’s do this.

FYI – All names have been changed to protect the privacy of the women in question.

Day 5 – woman number 1 – Cherise

After having backed out of 2 opportunities to approach random women this morning, I found myself walking towards a blonde who was about to cross the road and decided to man the hell up and say hello. She looked at me with the same startled expression that every woman has thus far but that startled expression was actually accompanied with a smile. I asked her name and what she was up to and in the biggest New York accent I’ve heard all day, she told me she was called Cherise and was on her way to work. Now I was about to follow up with another question (I honestly can’t remember what) but before I could even get halfway through my sentence, Cherise said ‘I’m sorry, this is really, really, really sweet but I’m very late for work and have to run. And with that she bounced harder than Tigger from Winnie the Pooh.

Woman number 2 – Elizabeth

About a minute or two after I encountered Cherise, I literally bumped into another woman who was walking towards me. I doubled back on myself and walked and chatted with her for about a minute and it turned out that her name was Elizabeth and that she too, like Cherise, was on her way to work; albeit at a design studio. Midway through the chat she lifted up her hand to show a great big shiny ring and said ‘Oh and just so you know, I’m engaged.’

I asked how long she’d been engaged for and she said for a year and that she’s getting married in June next year. I told her to take it easy and she said the same before walking off to work with a real spring in her step.

5 days down, 45 to go.

Thoughts

First things first, it definitely seems like approaching women who are on their way to work is a bad idea, but then any idiot could have guessed that. Still, what’s becoming extremely clear is that there’s very little to be worried about where approaches are concerned. I’d say that the majority of women I’ve spoken to have been flattered and that those who weren’t didn’t do or say anything that I couldn’t handle.

Still, what’s clear about this challenge is that the real fear in approaching a woman doesn’t come from the potential to be shot down or insulted but from the damage that happens to your self image when someone says ‘I’m rejecting you in a romantic context. You’re not my type and simply don’t do it for me.’ That might not be what women are thinking when they say no, but it’s how most men take it and that can be devastating.

We all have stories about who we are that we like to tell ourselves and approaching someone in this way brings with it the potential to either have your positive self image destroyed, or your negative one confirmed. Not many people are prepared to deal with that.

FYI I’VE STARTED A WHATSAPP GEOUP FOR MEN WHO WANNA BE AMAZING WITH WOMEN. DM ME IF YOU WANT IN