Getting to know people off-line in the real world
So, I've started taking and bike riding with a cute single girl (well, I'm 99% sure she is single now), this is my problem. I've talked to her for 5 hours and yet I know more details about a lot of you guys than I do about this girl I like. I'll be the first to admit that my social skills aren't the best, but I'd rate myself a 9/10 because we can have a conversation without long pauses or nervousness.
The issue is with how slowly I am learning about her. I would love to ask her 20 questions, but things like 'What are your sex fantasies?' would probably not go over well at this stage. Say what you will about the amount of information that people willing divulge about themselves on-line, but I would rather know it (and not have to ask the hard questions) than ask probing personal questions. It's almost as if I should get MI6/ASIS/FSB to spy on her and fill me in. But I wouldn't do that, and it isn't so much what she is doing in her life currently that I don't know (or feel I can't ask about). It's who she is, what she believes in, what has happened in her past, what are her likes/dislikes, does she ever get angry, medical issues, and other things like this... On forums and social networking sites, there are those surveys and other ways to learn who people really are. But it is much harder trying to come up with good questions ahead of time.
And, I am taking things slow and learning a little more about her each time we meet, but when does it become acceptable to push the boundaries with the personal questions? Are there any questions that you can think of that would be a little more flirtatious and personal than what a regular friend would ask?
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