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Like ninja first said I've a few stock questions / games.
- random questions - superhero power, cats or dogs, fantasy or fiction, action or comedy, earliest memory, ever do that "pornstar name thing, you know your first pets name followed by your mothers maiden name or vice versa, mine is ... . Any of these are able to give you something to move on too, poke fun of, answer back! Or even allow you to game with push pulls or c&f.
EXAMPLE: HB- if I could have any superpower in the world I'd be invisible. You- Why, so you can sneak in to the mans changing room and check me out or do you just want to go rob a bank?
- News question: whats going on locally or globally? Opinions, facts, the omg did you see blah blah
- Games: I saw it on here somewhere "5 lies game" but the one I always do is 2 minute truth. Tell her she has 2 minutes where she can ask you any question no matter how personal and you'll answer 100% true. In order to do this though you better be able to talk a lot and think fast. If you keep your answers short she might get the confidence to ask questions you dont want to answer. If you pad your answers out when that awkward question comes up you can go I'd love to answer but your 2 minutes are up...next time maybe?!
I really like those questions, but how do you create a setting where you are able to ask those? Randomly blurting them out whenever there's an awkward silence seems desperate.