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So there's a girl who I used to know when I was a kid, but we were mostly just acquaintances through our parents who are good friends. Started talking to her online recently through social media, I'm noticing little things about her personality that I really like (plus she's pretty so there's that). I've talked to her a couple of times and it's just sort of been like casual hey how have you been what are you doing these days etc. (the micro-elements of the conversations were more lively than that, I think she was mildly entertained). Our parents are still close so there's pressure not to screw anything up or move to quickly in my view. I wouldn't mind talking to her more but as the guy I feel like it's ultimately my responsibility to keep the conversation turning and alive, it's not that she isn't engaged in it but I think I have to be the major driver, at least so far.


The problem is I don't really know how to pace things out, like when to ask about meeting in person. I doubt she really knows whether or not I'm just trying to be friendly or digging or a little more, although I wouldn't be surprised if she suspects the latter after this last talk. There was almost a week in-between our two conversations, mostly because she was at a busyish period during the first one so I decided to keep it simple and cut it short on her behalf (saying I had some things to do) so as not to annoy. After we had talked for awhile the second time I was again the person to end the conversation, this time my excuses were pretty legitimate but could have easily been post-poned. Part of the reason I decided to do that was to end after what I felt like had been a naturally paced talk that showed I was interested in her life, and to end on a high note. I'm sure she's got some minor questions after the last conversation about why I'm really talking to her again all of a sudden and I was kind of thinking that she'd look into my posts a little bit (I make interesting social media posts when I'm trying what can I say) as a way to satiate the short-ish form conversation and see if I'm single etc.


I guess I just don't know how long to expect to do this. I've got a good reason to check in on her tomorrow (she was home with a minor illness so I'll ask how she's feeling etc., I mean my concern isn't fake but it's just also a good opportunity to show that), should I just focus on casual stuff? I already think that she probably feels like I'm someone she could vent to, at what point do I show concrete interest beyond friendship? Before or after we meet in person? Should I try to set up an outing? All of my potential wing men are fathers now who are usually busy or don't really do sociable things anymore aside from maybe catch a new movie but I don't know if that's a great group date setting to be honest. If women tend to prefer a direct proposal of interest and if I should just ask her out then I guess that's the route I'll go, I'm just not sure how often/long we should talk before going there. I'm actually an introvert and I've only really picked up a handful of more alpha mental traits over the past couple of years, she seems to be more moderate, but slightly introvert leaning. Are there specific personality traits I should try to test compatibility for first? I'm really drawn to her for some reason but like I said, the circumstance of how we know each-other means pressures on, more than it would be with a stranger. I'm sure I'm overthinking this on some level but any experienced conversational or pacing advice would be really appreciated.



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