So long story short I made a deal with myself to try and approach a girl during the day before the end of the month. 31 days through and the time was up and I had to go for it or forever be trapped with my insecurities.

This was big for me given that I had never really tried just straight up day game before and the only times I would ever really approach a random is when I was drunk.

So, I went roaming around the city waiting for a good opportunity with a pretty girl. A good opportunity basically consists of her being alone, no headphones, and away from large crowds that may hear my failure. I saw a cute girl, no-one around and knew I had to go for it, because nothing was stopping me now. There it is, what I was waiting for.

Cardinal sin number 1 and I approached from behind. I find it hard to approach from the front let alone at all so I know that was bad on my part but for now I needed anything I could get. So basically made a slow jog over to her and basically the conversation went like this.

"Excuse Me, Can i stop you for a second. What's your name?"

  • Oh, I'm Jane

(I already noticed she was surprised and a little "Wtf is this guy doing?" feeling.

"You are just really pretty and I wanted to come say Hi"

  • Oh Thanks :S

(Basically at this stage I didn't think of what I was going to say next so...)

"Do you want to head out for a drink sometime"

  • I have a boyfriend

"Oh no worries, thanks, See you later"

I was happy with everything up until I asked her out, given we had hardly spoken and we knew nothing about each other so basically I get that was my mistake. In a perfect world, and let me know if this is not what to say but, I should have said "What are you up to today?", "Are you on your lunch break as well?", then I probably would have gone with the number/date line. Would that be sufficient amount of chatting to warrant an ask out. I don't want to hold up anyone, then they would just get pissed off want to leave.

I also shook her hand when I introduced myself. Is that weird? Is that like job interview type shit that I should avoid or is it fine?

Anyone ant advice on how they could have gone better would be great.

Basically I am like everyone on the subreddit and find it near impossible to talk to girls like that and you know what. It was fine, I feel so much better and feel I can do that again and again. Next month I will up to once a fortnight and go from there. But I know how everyone says 'just go for it' and 'You will feel better afterwards' and that is exactly right.