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 24 – woman number 1 – Valerie

Guten tag homosapiens! Tis I, Ciaran Callam; back once again (‘for the renegade master’) for another exciting instalment of 100 Women in 50 Days, the blog where I risk embarrassment and rejection by approaching 2 random women on the street for 50 days.

If you’ve been following this blog, you’ll know that I tend to spend an ungodly amount of time in Starbucks and guess what? Today was no exception. Anyway, I was in my beloved coffee shop of choice today and working on a video for my YouTube channel when I saw a really pretty brunette sat opposite me talking to 2 friends. Truth be told; as pretty as I thought she was, I actually thought she looked familiar too and I couldn’t work out where I knew her from. It also looked like she and one of her friends were periodically looking over at me so I thought maybe there was a good chance I did know her.

Now before I went over there, I was once again struck by my age old nemesis of public approach anxiety. I mean, sure; the coffee shop itself was quite loud so we wouldn’t be overheard but the woman  of interest was sat with 2 friends and by jove, that thought did give me some pause. Still; I’m proud to say that I didn’t really hesitate for long, maybe 30 seconds, if that. Once that happened; I went over there and said:

ME: Hey, I’m sorry to interrupt your conversation, but I’ve got 2 things to say to you.

HER: What’s that?

ME: Number 1, I think you’re incredibly beautiful.


ME: And number 2, I genuinely can’t shake the idea that I know you from somewhere.

HER: (In a heavy French accent) Well, I believe that is not possible, because I am from France and only here for short vacation.

In any event, I asked if I could stay and chat with her and her friends but she said that they were just about to leave. I then told her about this blog, gave her the url and asked if they’d all would like to take a selfie with me. She agreed, and when that happened; yours truly got to snapping, told them to take it easy and got to bouncing.

And that’s exactly what they did.

Woman number 2 – unknown

The second lady of the day was a European looking brunette who smiled at me as we passed each other in the street. Once that happened, I looked back to see her looking back and still smiling and thought it would be crazy to not say hello. Now before we continue I’d like to say how rare an occurrence this is for me. When I was a little boy, women smiled at me all the time, but once I hit the age of about 14, those smiles dried up like a shriveled old old prune. Nowadays, whenever I make eye contact with a woman they nearly always look away so taking that into account, I’m sure you can see why I might see that as an invitation to at least say hello.
But as fate would have it, my approach didn’t at all go the way I thought it would. Not in any way, shape or form. You see, I made my way over, and let her know that I’d noticed some eye contact and thought it might be nice to chat and she said ‘No, no, no, no chat. I only smile to be friendly. Goodbye.’ And took off down the road like an olive skinned Olympic speed walker.

Who’d a thunk it?


Something happened to me over the weekend that’s really put rejection into perspective for me. Loosely put, I had a very painful experience that in retrospect was infinitely worse than anything that could happen when I approach someone. In a strange way I’m glad that thing happened because getting through that has showed me that I can overcome anything. Sorry to be so vague but that is the truth, yours truly has gone through some deep shit in his private life as of late. But you know what they say about whatever doesn’t kill you.

24 days down, 26 to go