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 21 – woman number 1 – Mari

Early this morning I was relaxing my derriere at Starbucks while getting some work done when I saw a pretty blonde walk from the till to the door and then sort of hover around in that area while doing something on her phone. I told myself ‘If she actually leaves this place, I’m gonna approach her.’ and lo and behold, that’s exactly what she did. I jogged outside, stepped in front and let her know that I thought she looked amazing.

Here’s what happened next:

HER: Oh my God, wow, thanks!

ME: Not a problem. So what’s your name and what are you up to?

HER: I’m Mari and I’m just on my way to meet a friend.

ME: Mari, I’d like you to have a coffee with me.

HER: But I really can’t, I’m like, literally just on my way to meet my friend up there!

ME: Ah, so in that case, I’d like your number.

HER: I’m sorry but I can’t, I’ve got a boyfriend.

ME: But do you really? That sounds like some premeditated bull manure to me.

HER: (Laughing) No, I swear to God I do. We got together last year on August 27th!

ME: (Laughing) Wow, that’s a very specific date. So you probably do actually have a boyfriend!

HER: I actually do have a boyfriend!

ME: Well in that case, I want to tell you about this daily challenge I’m doing called 100 Women in 50 Days……

And after that I told her about this blog, gave her the url, snapped a selfie with her and then bounced back to work like a chocolate coated Mexican jumping bean.

Woman number 2 – unknown

The next woman came a few hours later, and was a Mediterranean looking lady in fitness gear who was walking towards me at a brisk pace. I stopped her as she walked by but she said ‘I’m sorry, I really can’t stop I’m very late I’m sorry!’
I thought about walking with her but I eventually didn’t for two reasons. Firstly; she seemed to be genuinely late for something and I didn’t want to bother her. secondly, I was a little stung by the swift shut down and lacking confidence.

Cest la vie.


My interaction with woman number 2 had me thinking that I should find someone else to approach if only to hopefully have an interaction worth writing about, but I didn’t find anyone on my travels. Well, that’s not strictly true, I did see someone who was walking with a friend but everything about the two of them gave off the mature married women vibe. That in conjunction with a random outburst of timidity, had my balls shrinking right into my body and resulted in their owner doing absolutely nothing. Still, why should I have to find someone else to approach anyway? If the interaction with woman number 2 was unsatisfying then that’s exactly what it was and all it needed to be.


Anyway, because everyone keeps asking me to follow up with info on the women I swap details with, I’m going to say that I have a date tonight with one of the ladies from a previous day. In order to respect her privacy I won’t say who, but there you go. Ciao for now, humans.

21 days down, 29 to go