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First of all, try having conversations in person. They work a lot better.
Secondly, if it's difficult for the two of you to sustain conversation in person, you might want to look elsewhere. I've known girls who I have a lot in common with (just about everything in common. I'm pretty sure one girl was just about the perfect woman for me. Similar philosophy, religion, politics, and she could ski). But with that girl I just mentioned, you couldn't get her to open up about anything. With most girls I know, whether I've liked them or not, I have no problem walking into a room, sitting down next to them and starting a conversation. Part of it is me being outgoing enough to do it, part of it is her being involved in the conversation. But with this one girl, there might have been one or two instances where we actually connected and had a sustained conversation. One or two instances, when we spent a lot of time together in classes/extra-curricular activities. It took me a while to realize, but I eventually found out that there was no way we could connect in a committed relationship if we couldn't connect while we were still "just friends". It's a shame, though, because I really think me and said girl had a lot of potential. It was (is still, I think) clear as day that this girl liked/likes me, and she makes some attempts to have conversation, but although we have a lot in common, our personalities are too different. As that song goes, you have to know when to fold 'em. It saves you a lot of trouble in the long run.
So, in short....
1) Have conversations IN PERSON. Online conversations just aren't a good substitute.
2) If you can connect and sustain a conversation in person, then you're in the clear. If not, then you've got some thinking to do.
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