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 25 – woman number 1 – Dionne

Hey everyone. I’m now on day number 25 of this challenge which means I’m officially halfway through and have spoken to 50 women over the last month. That number makes my eyes widen when I really think about it. That’s like one and two thirds of a school classroom worth of dames and seeing them all lined up next to each other would no doubt, make my eyes widen. In any event, lady number 1 of the day was a mixed race girl with blonde highlights in her hair who was sat opposite me in Starbucks a few hours ago.

I saw her talking to a guy as I made my way downstairs for a latte and made a decision to approach her when I came back up. I told myself that I’d ask if they were an item (they clearly weren’t) and that if she said no, I’d politely excuse the intrusion and ask for her number. Now I was pretty nervous about doing that. Rare is the man who will approach a woman who’s actually with another dude, but like I said; it didn’t look like they were an item and I wanted to push myself so I thought #fuckit.

In any event, after psyching myself up while waiting for my coffee, I eventually came back upstairs to see that the dude had gone, which was both relieving and disappointing at the same time. She was now sitting on her own so I just walked over and politely asked if she’d mind me chatting with her for a while. She smiled and gave me the nod, so sit down I did and chat we did. Now there was a slightly nervous energy in the air at first, but after maybe 10 minutes that was completely gone and we were just laughing and joking with each other. We ended up talking for at least an hour, bantering back and forth and teasing each other about any and everything we could think of and I totally forgot about all the work I had to do.

About halfway through the conversation, I asked for her number so she pretended to not understand, and then asked me to repeat the question. That then made me pretend to not remember what I’d asked and that resulted in us having a 10 minute stalemate over whether or not we’d give voice to the question that neither of us was willing to admit we remembered. This is the kind of interaction I had with this girl! Anyway, after she eventually gave me her number, we carried on talking for maybe another 20 minutes before I peeled myself away to get back to work and she went back to answering work emails.

I think this is probably the best experience I’ve had so far during this challenge. We literally got lost in a conversation for over an hour and that’s a really cool thing. Goes to show the things that can happen when you step outside your comfort zone.


Woman number 2 – unknown

Two hours later I was walking home through Shoreditch in the early evening when I saw woman number 2, a Persian (I think) girl who was walking along and chatting with her friend. Now I was on a bit of a high from my chat with Dionne and also quite eager to make up for not being able to approach her when that guy was there so I made sure to not miss the opportunity. I took a moment to steel myself, walked over and asked the friend if I could speak to the girl I was interested in.

The friend honestly seemed quite uncomfortable when I did that. There were no smiles, no laughter or anything resembling warmth or comfort. I thought I was being charming but it looked like she thought I was just weird. In any event, the friend said ‘Yeah I guess.’ So I told the one I was interested in that I thought she looked incredible. She looked at me with confusion plastered all over her face. It was weird, I don’t know if she didn’t like what I said, or was unimpressed that someone like me had said it to her. Or having said that, maybe she was just really shy? In any event, it wasn’t long before she took her friend by the hand and sped off with her down the road.


I think today pretty much sums up what’s likely to be the main takeaway from this challenge which is that while you’re not going to be everyone’s cup of tea, you will be somebody’s. One woman’s poison is another woman’s elixir, so to speak. I approached 2 different girls with wildly different results; one I ended up losing an hour laughing and joking with, and the other just couldn’t get away from me fast enough. I guess the only way to find out how someone will react to you is to take a chance and say hello n’est pas?

25 days down, 25 to go