The reason it is "hard" for you is because you are thinking of all the gamey bullshit you are reading on here. You talk to friends and family without a hesitation right? You express your opinion and point out an observation correct? So, why does that change when you meet another person you aren't as acquainted too?
You lost me at "gamey bullshit". I thought that was RSD's mantra being all natural etc. Anyway, i am not saying going all natural and without routines isn't going to work but for a beginner, it is better to have some interesting things to say than just expressing whatever is on the mind especially when guys new to game don't even know what to say to a girl.
I started off by being indirect and asking for directions, it is such a low risk opener that getting blown out from that is impossible so it was easy to continue doing this. Transitioning was even easier, there are shit ton of things you can say to transition, nowadays, after opening i just tell her i don't really need to know the directions and wanted to talk to her but i can do that without coming off as creepy because i am more relaxed now.
I can't imagine how the reactions would have been if i just approached with a hi or whatever was on my mind being all nervous that i was. Actually i do, my second cold approach i opened a girl who was in the same exam room as me (from different university) right after school and she wasn't very receptive (i asked her how her exam was). Thinking back, my approach was a mess, my voice cracked and i was hella nervous.