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 22 – woman number 1 – unknown

Woman number 1 of Day 22 was a brunette who was walking towards me while I was heading to Victoria train station. Now I’m not a guy who likes using chat up lines, and if you’ve been following this challenge you’ll know for a fact that’s true.

But; I came across a line yesterday that I found hilarious so today I decided to test it out and see what happened. With that in mind; I approached the mysterious brunette and said:

ME: Hey, I saw you walking towards me and thought I’d risk humiliation by trying to flirt with you. How’s it going?

HER: Oh my God, that’s really sweet, but I’m very, very, very late for work and I have to go, sorry!

This is literally what she looked like when she took off.

And with that, she sped off down like Road Runner from that old Warner Brothers cartoon, never to be seen again.

Meep meep!

Woman number 2 – unknown

Woman number 2 was a Middle Eastern girl who was walking through Victoria train station and talking on her phone. Now I knew that approaching her then would have a very low chance of success, but I thought #fuckit. Why the hell not? Who was to say what would happen if I gave it a shot? Maybe she’d be so captivated by my masculine aura that once our eyes met time would slow down and she’d gaze at me with this transfixed look of wonder as every limb in her body went limp? Maybe then she’d slowly return her phone to her mouth and say ‘I’m sorry but I’ve got to go. The most gorgeous hunk of a man has just approached me and I need to engage with him. I must be in his presence. I must find out exactly what this prime specimen of manhood desires from me and give it to him immediately. He’s now my main priority, catch you later.’ Before abruptly hanging up the phone and giving me her complete and undivided attention. You might think that scenario to be unlikely and to be frank so did I, but it wasn’t impossible. It might actually have happened.

In any event; all you naysayers out there who thought she’d probably tell me to go make love to myself were correct. In fact, the very second I got near this woman she snapped at me and said ‘Don’t talk to me, I’m on the phone!’ before speeding off down the road like the 2nd Road Runner of the day. She reacted so quickly it’s as if she already knew I was there and was waiting for me to try something.

Meep meep!


I don’t feel like I want to do this anymore, and It’s been that way for a couple days. The hassle and pressure of going out every day, finding girls to approach, facing rejection, and then writing about it is weighing down on my soul and it’s like this challenge is taking up my life.

Still; I knew that this day would happen and that’s exactly why I decided to do it so publically. I knew that if I did it in secret I’d be able to quit just as privately whereas doing so now will mean I’ll have an unfinished challenge on my site and plenty of disappointed onlookers.

Oh and that’s not to mention the lack of respect I’d have for myself too. So I’m gonna keep going. I’m gonna press on. I won’t give in to the grim spectre of self-sabotage and I vow to see this thing to the end.

That’s all folks!

22 days down, 28 to go