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Just looking for advice or an opinion on this situation. Met someone online and chatted for about 3 weeks. Conversations were flowing easily, with each of us messaging first on different days. He mentioned meeting up sometime if the convo kept going. About a week later I suggested lunch and we picked a time and place. Lunch was nice but the conversation didn't flow as easily. I admitted that I hadn't dated/met anyone in almost 20 years and that I was feeling a bit awkward. He actually laughed a bit and said he understood and that he always feels awkward meeting up the first time. That broke the ice a bit but it was still difficult to find things to talk about. Lunch ended and we went our separate ways. I messaged him later that night saying that despite the bit of awkwardness I had a really nice time and figured I wouldn't hear back.

Well, here it is another 3 weeks or so later and we're still messaging eachother every 2-3 days. Again, each of us messaging first on different days, asking questions about things said in previous conversations so I think showing actual interest in eachothers days (?). Some messages are flirty and some are just casual. But neither one of us has mentioned/asked about going out again. I think I would like to see where it goes but am not sure about making the first move again.

What the hell do I do here?? Or do you think he's not interested and is just being friendly/polite? And men, how would you feel if you were the guy in this situation and the woman was the one initiating?

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7 months ago