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everyone is different, one person might feel like you are sexually harassing them while another might just find it weird in a funny way and enjoy how out of left field a question like that is coming from a stranger
I don't recommend asking strangers how often they masturbate, if you are going to try something bold I suggest you just start asking about their current dating life and boldly show some interest in being a part of that life without shame, try to just get them to come with you somewhere to talk further for a little date and maintain that you have interest but want to find out more and the sooner you guys go out for some personal time, the better
it also makes more sense to me that you would try to actually build some rapport with someone to get them more comfortable with you before coming at them with some topics that could make them slightly uncomfortable outside of a private situation with someone they trust
when a girl actually likes you as a person and finds you physically attractive, you will find that this sort of thing is fairly arbitrary and doesn't really help you all that much, you could get laid doing this, but I doubt doing this would be at the core for why, it would be more likely that the girl you met was just attracted to you and went along with it
just don't think of it like you actually have to do something to make a girl attracted to you, just pay attention and it should be fairly clear to you when someone is interested in getting to know you better
think of it more like a partnership, where both sides need to cooperate and participate
I know for myself personally, it is a big turn off when a woman is too forward, I have had a few older women be very very straight forward with me when I didn't know them well at all, it just made me feel really uncomfortable rather then turned on
Well, yeah I would build some rapport first with the girl and then ask risky questions. Though, are u saying that after it built enough rapport a girl that I should ask questions like "do you have a boyfriend?"