I think to a first-order approximation it doesn't matter where I want the conversation to end up because the person I'm talking to will have an obvious hypothesis about that. But let's say I'm looking for women to date for the sake of concreteness.
Sorry, I have no experience with that, so I lack useful advice. 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.
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.