I've met with three new people under my Craigslist Friend Project and I think I can finally say something about it. One thing I noticed during all three meetings is my tendency to feel comfortable when listening, but very uncomfortable when talking. Particularly when talking about myself. I respond to what others say with eye contact, head nods, and murmurs of agreement/understanding, and I have no problem finding the appropriate places to interrupt the person while they're talking in order to ask quick clarifying questions ("Wait, so this was before you were offered the job or after?"). This behavior is totally automatic for me and comes from being sincerely interested in the person talking. In other words, I'm an expert active listener.
However, I don't respond well when other people are sincerely interested in me. If I get asked a factual question like "Do you have any siblings?" I answer tersely. If I get asked a more personal question like "How was your weekend?" I speak vaguely or try to pass my answer off as trivial by saying something like "Pretty boring" or "It's a long story." Even if I don't say those exact words, the intonation of my answer is enough to suggest that I don't think what I'm saying is worth being interested in.
The questions I have the most trouble with are questions more directly related to identity ("What kinds of things are you interested in?" or "What skills do you have?"). The most notorious of these questions is, of course, "What do you do?" You've probably been asked this question just about every time you've met someone new in your adult life. I could write an entire book on "What do you do?" but the main problem I have with that question is that it links my personal identity to the projects I've obligated myself to. As a person who is admittedly obligated to very little, I feel like telling people what I do is a poor means of telling them who I am, which is really what they're asking.
I was recently at a barbecue attended mostly by older adults. "What do you do?" came up a lot between them and the conversations invariably revolved around the social roles each person felt they filled. There was a math teacher who only discussed his math classes, a social worker who just talked about the state of society, and a software engineer who contributed to conversations primarily by tossing in computer programming jokes. Even note my wording there. "A math teacher" versus, say, "a person who teaches math." It sounds perfectly normal to say that the thing they contribute to society is equivalent to who they are. And based on what these people wanted to talk about, it's reasonable to assume that they identified themselves by these contributions, too.
The work you do to enrich your society is the first (and sometimes only) piece of information people use to discover what type of person you are. I'm not saying that's a bad thing. It's actually an efficient way of learning about others and helping others learn about you since what a person does is often reflective of more complex components of their identity such as their values, skills, beliefs, or interests. It just puts me at a disadvantage. Telling people I'm a student is basically my excuse for not having a social role into which they can neatly box me. I don't really "do" anything. I don't have a career, long-term goals, a particularly developed skill, a robust knowledge on any valuable subject, or even a strong interest in any one thing over any other thing.
My answers to identifying questions don't represent the type person I am and the only thing I can do to protect my ego from that fact is to avoid those questions altogether. Right now, the type of person I am is the type who spends his time and energy trying to figure out what type of person he is. That's difficult for me to express and even more difficult for others to accept. It seems that to be comfortable telling people about myself, my options are to either find the kind of identity people expect me to have or to be okay with the fact that I just don't have that. Self-discovery might be an endeavor too big for the Craigslist Friend Project, but we'll see how far I can get.