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

FYI - Every Woman I’ve taken a selfie or shot a video with has given her expressed permission for me to do so. They have all been fully informed about this challenge and were more than happy for me to post up their pictures

Day 7 – woman number 1 – Aneke

So this morning I found myself once again on the tube and once again sat next to an attractive female stranger with whom I wanted to chat. The lady in question being a blonde businesswoman who was watching what looked like a TED Talk on her iPhone. Now; if you’ve been following this challenge for some time you’ll know that I’m reticent to approach women in quiet areas with eavesdroppers aplenty and today was no different. Still, I’m pleased to report that what I couldn’t do at all on the first attempt, and what took me over 30 minutes to do on the second, I did today after only 2 minutes!

When we spoke, she told me her name was Aneke and she was (and presumably still is) a Canadian reporter who was on her way to work in Notting Hill. She said she was pleasantly surprised when I spoke to her because ‘Not many people do that in this country.’ and that quickly led to me telling her about both this challenge and my previous one, 100 Days of Rejection. She was really impressed by both and said that she did something similar recently when she asked out her hot doctor who sadly turned her down for ethical reasons. Now, it was at this moment that I asked her if she would turn me down for ethical reasons, were I to ask her out, to which she replied, ‘Sadly yes, because you’re not even remotely my type. But you do seem like a great person, so if you’d like a new friend then I’m game.’ She then asked me if I’d had any success from this challenge and I told her that it was surprisingly more than someone would expect and that I was actually on my way to meet my Yoga teacher from day one at that very moment. After that, we swapped numbers, said goodbye, and I bounced further and further than a well pumped basketball slammed hard into the ground by the Incredible Hulk.

Woman number 2 – Katie

See our selfie here

Woman number 2 was walking through Shoreditch with a bag full of shopping and a smile on her face when I stepped in front of her path and said what’s up. I asked who she was and what she was up to and she said she was Katie and she was doing her Christmas shopping. I then asked if that was a good enough reason to skive off work and she laughed, saying that she had the week off and would be working this weekend.

She seemed a bit nervous at this point, but to be fair so was I. I literally stepped right in front of her and was making a point of being comfortable with the discomfort of the situation, which meant not rushing to fill the gaps in conversation and maintaining eye contact.  Both of the above created a powerful charge to our communication which was fun but alarming for us at the same time. Now I don’t remember exactly how it all happened, but I basically ended up telling her about this challenge, giving her a link to the blog, adding her on Facebook, taking a selfie with her, and giving her a hug goodbye.

Thoughts

OK so if there’s one thing that’s becoming quite clear about all of these approaches is that you don’t need a ‘chat up line’ to meet women on the street. If you have an awesome one then by all means knock yourself out, but they’re not necessary. All that really matters is the personality you have and the energy you’re putting out to her, so I think that as long as you come across as a good, genuine and confident person, you’ll be just fine. Now that’s easier said than done but I think two things that are helping me right now are the fact that I both meditate and do yoga a lot and also that I’m getting lots of practice at being in these situations. Meditation and yoga are great for mental strength because they place you in great discomfort for extended periods of time and doing them both regularly takes the edge off real life.

Also; getting reference experiences of being in certain situations makes it easier to deal with those situations for obvious reasons. You might be shy before your first ever keynote speech to 1000 people, but after your 77th, it probably won’t bother you as much.

7 days down, 43 to go

FYI I’m starting a whatsapp group for men who want to be amazing with women. DM me if you want in.