Given your uncertainty about how to proceed, I suggest the possibility that this set of circumstances is not the easiest way for you to achieve the goal you identified.
I am wary of this reasoning. It would make sense if one was uncertain how to pick up women in bars specifically but was quite familiar with how to pick up women in a different environment. However the uncertainty will most likely be more generalised than that and developing the skill in that set of circumstances is likely to give a large return on investment.
This uncertainty is of the type that calls for comfort zone expansion.
Environment matters a lot. Bars (for example) are loud, dark, sometimes crowded, and filled with inebriated people.
I CANNOT STRESS THIS POINT ENOUGH:
Thinking in terms of "picking up women" is the first problem. One should take the approach that they are "MEETING women". The conceptual framing is important here because it will influence intentionality and outcome.
A "meeting" mindset implies equal footing and good intentions, which should be the foundation for any kind of positive human interaction. Many women are turned off...
r/Fitness does a weekly "Moronic Monday", a judgment-free thread where people can ask questions that they would ordinarily feel embarrassed for not knowing the answer to. I thought this seemed like a useful thing to have here - after all, the concepts discussed on LessWrong are probably at least a little harder to grasp than those of weightlifting. Plus, I have a few stupid questions of my own, so it doesn't seem unreasonable that other people might as well.