So a reframing of this question is “what do you say/do/act to gain information about what a person would like to be asked without resorting to one of these sorts of questions?”
(With a side-note of “the hard mode for all of this is when you actually do kinda know the person, or have seen them around, so it is in fact ‘legitimately’ awkward’ that you haven’t managed to get to know them well enough to know what sorts of conversations to have with them.)
So a reframing of this question is “what do you say/do/act to gain information about what a person would like to be asked without resorting to one of these sorts of questions?”
(With a side-note of “the hard mode for all of this is when you actually do kinda know the person, or have seen them around, so it is in fact ‘legitimately’ awkward’ that you haven’t managed to get to know them well enough to know what sorts of conversations to have with them.)