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 18 – ‘woman’ number 1 – Louise

So I’m not at all proud to say this, but I almost picked up a 16 year old today. The thought makes me feel sick, but the facts are the facts and that is what happened. Remember I said that the demographics of Birmingham are different to those of Central London? Well never has a truer word been said. In Central London, especially the Shoreditch/Hoxton area I live in, everyone’s at least 21 years old and no older than about 45. It’s an area that creative/professional people move to after leaving uni but not somewhere that people actually grow up in and it basically means I don’t have to put too much thought into who I approach. As long as I like the look of them, it’s all good from a maturity standpoint.

In any event, today I was walking along a train platform in Birmingham’s New St station when I saw a girl sat on a seat and decided to say guten tag.  This is what happened:

ME: Hey, I hope you don’t mind me saying this, but you look amazing and I just wanted to let you know.

HER: Oh my God, thank you, that’s such a lovely thing to say.

ME: So what’s your name and what are you up to?

HER: My name’s Louise and I’m just waiting for that train that’s coming.

ME: Okey doke, well in that case, how would you like to go for a drink some time?

HER: Yeah, that’d be good.


ME: Hold on, how old are you?

HER: I’m 16. How old are you?


ME: Older than that.

HER: How old?

ME: Older than that. Look, I’m sorry but I’ve gotta go. Have a great day.

And with that, I picked myself up and marched out of there faster than you could say ‘man’s got morals.’ I suppose something like this was always going to happen eventually but Jesus H Christ did it make me feel sick. Yuck.

Woman number 2 – Angelina

About an hour or two later I was in a Starbucks trying to wash the vile taste of pubescent female from my mind when I realised I needed a wee and ran upstairs to use the toilet. When I got there, I saw a woman stood outside waiting who smiled and laughed when she realised that I badly needed to go and that her presence would prolong my suffering. We chatted for a while before she went inside, a chat in which I carefully studied her face to assess her levels of genetic maturity and was pleased to discover that she was probably in her mid-twenties. Anyway, after the person who was in the toilet came out, she then went in, did her thing, came out, said ‘It’s all yours!’ and sat down at a nearby seat. At this point I knew I was going to have a proper talk with her, but I also knew I had to answer the call of nature so I went in, did my own thing, came back out, sat opposite her and started a 15-20 minute conversation.

Her name’s Angelina and she’s a self-proclaimed procrastinator from Venezuela with an oddly American accent. Sadly, she’s going to be ejected from the UK this month because of her expired Visa. I told her that if she needed a shoulder to cry on, I could provide that along with a series of caffeinated beverages and she said ‘I think I’ll take you up on that!’

We then swapped details and agreed to meet up soon to commiserate over her impending deportation.


The only thing I really want to say about today is that my encounter with the teenager had bile rising into my mouth and actually corroding the enamel of my teeth. Also, my encounter with Angelina pretty much sums up the spirit of what this challenge is all about, taking advantage of random happenstances and seeing where the hell they take you. It’s also interesting to note that I pretty much assumed the conversation I’d have with her when I left the toilet would be a good one. Now that’s not to say that we’d definitely get on so well we’d agree to meet for another drink, but I knew for a fact it’d be positive and that’s why I just walked over and sat down in front of her like that. I guess I’m getting better at picking up on social cues.

18 days down, 32 to go