One thing that isn’t often spoken about is how hard it is for men to approach women with romantic intent. 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.

See the whole challenge here.

Day 19 – woman number 1 – unknown

I was with my cousin Sabrina today when I saw a gorgeous black girl striding by. It might not have been my finest hour, but I found myself saying ‘Cuz, I’ve got to run off and handle something, back in a sec!’ before brisk walking after the unknown black lady. She quickly blended into the crowd so I had a bit of trouble spotting her but eventually I saw her heading into Selfridges so I ran in behind her. Once I got inside, I saw her heading down a packed escalator and followed before tapping her on the shoulder at the bottom and saying:

ME: Excuse me, I just had to let you know that you’re looking amazing.

HER: Thank you, that is a really nice thing to say, but I’m meeting my boyfriend in here and he wouldn’t like to hear you say that.

ME: You’re literally meeting him right now?

HER: Yeah.

ME: Oh well, he’s a hashtag lucky man. Take care.

Woman number 2 – unknown

The next woman was an unknown Japanese looking girl who was walking towards me outside Costa Coffee shop. When I stopped, said hello, and told her she looked incredible, she just looked at me with confusion plastered all over her face, like she didn’t know what the hell I was saying. In any event, after a few seconds of staring at me wide eyed and open mouthed, she took off like a bat out of hell. I don’t know if she didn’t speak a word of English or if she was just intimidated but it was weird nonetheless and I did feel a pang of rejection when she sped off without saying a word.


I might have said this previously but I think my mental state greatly affects the outcome of these approaches. I’ve been feeling pretty down today and I think that came across in my demeanour and body language. But then again, maybe I’m just seeing issues where there are no issues at all. Truth be told, I really couldn’t be bothered to do this challenge today and had to force myself to get it done. But get it done I did, and that’s another day in the books.

19 days down, 31 to go