sounds like chief is right, learning the confidence just to say hello to women is the biggest step, so you have done well to acheive that! and since you learned that when you were at work it seemed easy, it might help to imagine your new self as version b of your old self, think of the different thoughts and behaviours your new confident self would use, and think and use them. its a bit like being an actor or being in fancy dress, and just pretend to be that new you instead of being the old you. Nobody else will be any the wiser though, because they will only see the behaviours of the new you, and they will just think that is what you are like. Then pretty soon you will become that person anyway.
hint 1. girls arent all so confident either, however they appear - we hide behind our friends and our makeup
hint 2. you have absolutely nothing to lose from keeping going, and everything to gain, so dont get demoralised
hint 3. your ultimate goal maybe the top of the mountain but for now just concentrate on the baby steps,
increasing your confidence one day at a time and talking to more people, and try to see it as fun (play about like you said), because then you will relax more, plus the more you do it the easier it will get, the rest will come, being scared you wont know what to do if some HB responds and you dont know what to say should be the least of your worries tbh, maybe she will respond and it will work out great, if not then hey you gave it a shot, either way it wont be the 'opportunity of a lifetime', lots more opportunities will come along i promise!
