1st vs. 2nd conversations; social clumsiness vs. fear

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I've noticed that when it comes to small talk situations, I'm better at first conversations than at second (or later) conversations.

I mentioned this the other day to someone I've known for a long time, and was surprised when she said that she also finds first conversations easier. I was surprised, because she's much more socially aware/perceptive than I am. However, further conversation revealed that her reasons were quite different from mine.

I find first conversations easier than second conversations, because in first conversations, much of the conversation is often devoted to finding out basic data about each other. I can ask questions like "so, are you from around here?" "how long have you been in the area?" "are you a student?" (if yes, "what are you studying?" and "why did you choose that field?"; if they're working, "what's your job?") , and other such basic things, and they can ask the same sorts of questions to me. But when the second conversation comes around, the basic questions have usually been used up, and I often don't have anything else to make a conversation with.

The person I was talking to said that she found first conversations easier because there was less risk - she felt she could be herself without worrying about whether they'd like her or not, because if they did like her, then great, and if they didn't like her, well, that's too bad, but she didn't have a relationship with them to begin with, so she wasn't really losing anything. In a second conversation, on the other hand, the fact that they've come back to have another conversation with her means that they must like her a bit, or at least not mind having a conversation with her, so if she says/does something that makes them not like her, then she'll have lost a positive relationship, and she's afraid of that happening.

We both found it interesting how we had a superficial similarity - being more comfortable with first conversations than with second conversations - but that it was due to very different causes in her case and my case.

I said to her that it seemed like for me, it was more a matter of social clumsiness while for her it was more a matter of social fear, and she agreed with that assessment.

I feel kind of the opposite. I feel more anxiety about making a first impression during the first conversations, and I love factual information, but I can find the first exchanges of personal details awkward. I find it much easier to speak with someone I know very well; I feel that I can be more honest and that if I offend them or something (or the other way around), it is easier to work through problems like that when you know them, whereas if it were a first meeting, the other person would probably not desire any further contact with me.
I've never really thought about people preferring introductions to later conversations until now, but that's probably because that's not my opinion...

Mostly it's the first conversation that gives me the most difficulty, though I know where you're coming from with that "don't want to mess up the progress I've made" thing. I think these days I usually take it as an encouraging sign if I've made it past the first meeting though. Still, I've been known to avoid people if I see them and I don't feel ready to continue.

My performance can be sporadic - with one friend I made, we barely spoke to each other for months, then suddenly chatted away to each other like we were old chums, then nothing for a while, then we got it right again, and these days, all other things being equal, we seem to do better and better at every meeting, for now at least.