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 23 – woman number 1 – Amy

Hello everyone and welcome to another exciting edition of 100 Women in 50 Days! This is the blog where I, Ciaran Callam, go out and approach 2 random women every day in the aims of eliminating approach anxiety and inspiring others to overcome their limiting beliefs!

Woman number 1 of today was a blonde who yours truly saw sat at a table at Starbucks when he popped in for a quick decaf latte en route to the train station. When he saw her, he told myself that he’d say hello once he’d paid for and gotten his drink and when that happened, he followed through on that promise with no real hesitation. When he reached her he said:

ME: Hey, I saw you sitting there just now and thought I’d risk embarrassment by coming over and trying to flirt with you.

HER: (laughing) Is that right?!

ME: Yeah it is. Now I’ve got a train to catch in about 15 minutes but would it be OK if I sat here with you for a little while before then?

HER: Sure, no problem, sit right down!

ME: So, this is totally random, isn’t it?

HER: Very random. I just sat here for a coffee and now I’ve got some stranger here with me!

ME: So, I’ve got something to tell you.

HER: What??

ME; I’ve got absolutely no idea what to say next.

HER: Oh wow! So you don’t do this very often then?

ME: I actually do it more often than you’d think.

The lady in question was called Amy and she was on her way to a football club (can’t remember which one) to work as a waitress on match day. Apparently she got so hammered on the eve of New Year’s Eve that when New Year’s Eve rolled by, she was too hung over to do anything and stayed in with friends eating junk food. In any event, I chatted with her until it was time to get my train, took her number, and then told her about this challenge, to which she replied ‘That is so cool!’

We’re gonna go out partying at some point in the future. She probably thinks she can out last me but trust me, she has no idea who she’s dealing with.

Woman number 2 – Anya

Woman number 2 was a Polish girl whose name I’ve completely forgotten, but for the sake of consistency let’s just call her Anya. In any event. I saw Anya slouched on a seat at the train platform messing about on her phone, and used the same line on her that I used on the two women previous. Loosely put, she didn’t seem to quite mind my presence and was happy to chat about going to the gym 6 days a week, the fact she can do 40 press ups, and the crazy night out she’d just had and still not slept from; but I’d be lying if I said she was truly interested in yours truly.  In any event, her train eventually came, I told her to take easy and she boarded that son of a bitch the way that only a semi interested Polish girl can.


First things first (I Poppa, freaks all da honeyz) I want you all to know I’m officially retiring that chat up line. I tried it out 3 times, I had my fun, but it’s over now and I’m not going to go back to it because I don’t want this challenge to become some cheesy spectacle! It must have integrity, God damn it. Integrity I tell you!

Anyway, one thing that’s becoming quite apparent from doing this challenge is that if I spoke to every person, male or female that I found interesting then my life would get very interesting very quickly.

In the past few weeks I’ve found myself in some very unusual situations and have made some great connections with people I’d have never met otherwise.

Also; on reflection methinks I probably caught the Anya at completely the wrong time because she did seem to be seven shades of shattered when I met her. maybe if she’d had a good night sleep she’d have been more agreeable to my particular brand of personality?

Curiouser and curiouser

23 days down, 27 to go