How does one determine when to ask questions?

It is too vague to answer but usually people like it when you ask them good questions about what they are talking about or interested in, this is favourable to talking about yourself and own interests to them (unless they ask). Try to avoid asking obvious questions though

It is too vague to answer but usually people like it when you ask them good questions about what they are talking about or interested in, this is favourable to talking about yourself and own interests to them (unless they ask). Try to avoid asking obvious questions though

Your last sentence is an example of the bane of my social interactions. "Obvious," is a subjective term, what is obvious to one person is not obvious to another. There is also conflicting data; you say that people usually like good questions, and others have said that people do not like questions. They actually said "too many questions," but again, this is subjective, and thus useless in advice.

It is difficult not to be somewhat vague in my questions because I have trouble remembering exact details of conversations, and those conversations are in the past and (hopefully) won't be repeated, at least not word-for-word. 

I did not actually expect to get rules of conversation that I could use from this forum, but I recognize that I can be wrong, and so I asked the questions anyway. It appears to me that there are no actual rules, and that neuro-typical people have a sort of mind-minding. I know that it is not actual "mind-reading," but that phrase is useful to express my frustration.