I'm pretty bad at conversations unless the interface is clear. I'm not good at defining or building a conversation interface with a new person, and I think that's the main reason why I consider myself an introvert. A conversation interface, like any other interface, in case it wasn't obvious, is the visible set of options presented at any given point in the verbal (or visual) interaction between two people. For example, if I walk up to a friend, I can easily launch directly into any number of topics, but each one of those topics was most likely established via conversation contract at an earlier date. With a new person, we all know how dull that interface can be: where do you work, where did you grow up, when did you move here, are you married/dating/single, etc.
Extroverts are creative conversation interface builders. They can take something like "where you grew up" and develop that interface to reveal information that is novel and interesting. They can leap across inadequacies in the interface without hesitating: for example they could jump from "where you grew up" to "youth stories" to "personal philosophies on ideal communities" to "intimate details of unique personal relationships" without getting bogged down by the fact that the interface discourages easy access to the "intimate details stories" unless you're trusted. So how do some people use the interface more successfully than others?
I suspect there are some meta-interface properties that they're setting early... for example, good conversationalists usually indicate fairly early on that they are requesting permission to jump wildly from topic to topic. You grant that permission on a jump that is fairly trivial: going from "tales of taking care of ill grandparent" to "new technology advancements in cryogenics and other pursuits of immortality". Permission granted. But then the jumps become more personal: yesterday a friend of mine, in a conversation with someone he had just met (they were talking about whether or not there was a person for everyone), asked her "have you ever dated anyone that was uncircumcised?" Of course, that's pushing the conversation interface's flexibility quite a bit, but because the rest of the table acknowledged the risk of that question, new person didn't feel too embarrassed to reply. My friend therefore established a fairly solid contract for the rest of the night: he could ask any question, in fact, because we seemed to delight in his creative conversation, we almost expected the jumps to become wider and wider.
The conversation interface persists over time, of course. Permission that is granted between people in one sitting is still granted at another sitting (even if it's separated by years). That's why it's so easy to talk with friends even if you haven't seen them in a long time.
The best conversationalists can work the interface in such a way as to make it appear as if the other person was the one requesting permissions for wider jump access and personal topics. I'm so poor at it that I'm pretty sensitive to when certain people are making it appear as if I were a good conversationalist myself. I suppose it happens with leading questions that are very easy for me to turn around... and it just happens that those turned-around questions are linked to key permissions. For example, an innocent question about family might not bring up any new information from me, but when I turn it around they may bring up a unique family situation that involves death of a loved one or proximity to fame or other relationship drama. Suddenly it appears that I've been given access to a valuable topic even though I wouldn't have known to ask in the first place. Some people can use this correctly, but of course there are others that use leading questions to constantly lead conversation back to themselves, which is something that can close conversation interfaces down. If the balance of permissions being granted is lop-sided, it's the responsibility (or rather, the interface encourages) that some work be done to even the balance.
I wonder if I could map actual conversation interfaces between me and people I know. For example, I definitely know the short list of topics that are available with any number of my friends. If I want to talk about the new powerbooks (coming out this tuesday! really!) I know there are certain people who have given explicit permission to discuss that topic, and others (like K) who have expressly forbidden that topic (actually, she allows it, but follows up with much chiding and humiliation on my part, which discourages me from bringing it up). On the other hand, if I want to talk about cats, I have a fairly good idea of the interface that that topic provides with several people: with some it produces more cat stories, with others it turns into meta-cat conversations, with others it becomes general pet/baby stories, and with others it's not available at all. I can imagine a couple different maps: one organized by person, another organized by topic, that would give an outsider a fairly good understanding of my conversation interface and the interface I see in my relationships with other people.
I know you saw this from a million miles away, but what if this could be captured in software? Either as part of an email or IM client, or as a way to group people with similar interfaces regarding similar topics? How important is the person behind the interface, in other words. The only reason I don't talk to strangers about some of the things that I talk to friends about is because the interface hasn't been established... but if we explicitly accepted incoming conversations through a public conversation interface, we wouldn't have to go through the trouble of being introduced, meeting at a bar, testing the breadth and depth of allowed conversation jumps, establishing permissions contracts, etc, before we could talk about, say, "the purpose of life" or something else that is sensitive and generally requires a lot of trust on both sides.
This weblog, for instance, offers me a much broader conversation interface than I have with any actual person. The things I talk about here I do not have permission to talk about anywhere else. That's perhaps the essence of the power of weblogs... I get to invent an ideal conversationalist with whom I can talk and anyone can opt in to listen in on the conversation, even contributing according to the established open permissions. It makes me think that my hunch is correct: the people behind the conversation interface are important, but not as important as the interface itself. I know, any statement that claims the universe isn't people-centric is shunned by the community (I can feel it even now), but that's my hunch. Sometimes, relationships aren't about people but rather about the quality of the interface between them. Because the interface can be transferred between people if they converse in groups. It's easier to transfer an interface to a group of people from an individual that you've worked to establish it with than to build each one from scratch.
Which explains why it is easier and oftentimes more successful to meet new friends when you're with a core group of friends already.
So many different ways of looking at this and finding new interesting connections.