If it is a total stranger and you want to know if he is a dating material, you probably would want to know the basics such as if he works, can take care of himself and can keep his den clean. After all, is he can't do any of it, he wouldn't be a good candidate.
Try to word your questions carefully so that he won't feel like he is being interrogated. And don't have a judgemental tone. Be genuine and curious rather than inquiring.
Instead of asking what he does for a living and where he lives, you can say "What do you do at other times, when you are not talking to (or flirting with) strangers?" This will not only end up with an answer about what he does for a living but also will also fill you in about many other things he might be doing.
And instead of asking where he lives straight up, you can sneak it into some sort of conversation while talking about the local food market that you like to go when you get a chance and ask him where he lives and then finish it off with 'yeah, not too far from you, either" or accordingly.
I wouldn't want a chick asking me what I do and where I live and judge me based on that even before knowing me. And if those should be the questions, I would ignore them and try to catch the next space shuttle to get away.
I would keep it casual at first, until you decide that you are interested in each other. Ask about school, work, and what he likes to do. Try to find common interests to discuss. That'll make your conversation easier.
hotel I work at she is always glad to see me and she fusses about me I front of others and started to tell me I looked better without the mustache I think she is attracted to me I never had anybody do that before rarely had I had a women do that I am no brad pit or George Clooney have I made a mistake sending her chocolates for Valentine's day the hr officer set it up to send things like that for that special day I like her a lot but I don't want to lead her on what can I do about it signed lonelyguy
I know it says questions but even they start with question. One great question to ask in my opinion would be if he thinks with his head(the lower one) or his brain. This question will tell you a lot mainly if he's worth dating, if he is looking for a quiky and if he's serious or not. If he evades the question he's not serious.
Get to know what he likes. Music, hobies, opinions on issues. I've learned that a good man doesn't have to be "currently" employed, just recently employed and actively looking. If you really want to date a guy you don't want to let him think you are judging him so be free and open :)
OH, and be sure he has no criminal record...or at least not a violent or wreckless one.