Driving across this great country of ours has (as usual) filled me with the longing to know more about the lives of the people around me. However, I face the typical problem of the traveller: there is literally no reason for me to talk to the people around me. I've become fairly good at talking to people when there's even the thinnest excuse for me to do so (I've developed a whole technique for talking to people at parties, for instance). But I've still yet to leap the toughest of social hurdles: I'm not good at talking to people in situations that aren't really social situations.
In many ways, this is only sensible. I am a very large, dark-skinned man. People don't necessarily want to talk to me on the street. Furthermore, I think that people generally have a right to not be bothered by people they don't know.
However, it does make the world feel a little insular. Under current circumstances, it's very difficult for me to ever meet people with whom I don't share at least one common connection. Because of this, my knowledge of the world is pretty insular. I tend to only know people who: a) went to college / high school with me (or are friends with someone who did); b) belong to the sci-fi or literary fiction scenes; c) have worked at the World Bank; or d) are upper-class Indian-Americans.
On occasion, I would like to at least speak to people who are none of these things. I mean, we don't have to become best friends, but it'd be good to at least hear what their voices sound like.
As such, I've started to (very cautiously) explore the possibility of speaking to people I encounter in bars, aeroplanes, museums, stores, libraries, the street, etc.
I also have yet to ever do this, but I would like to somehow figure out how to talk to the 3+ people per day who wander up to me and comment on how tall I am.
So far, the main thing I've learned from this effort is that it's best to just be observant and comment on something in the environment. Since these people are strangers, it'd be terribly creepy to ask them about their lives. But if there's something in the area that piques my interest, asking about it can often lead to some kind of conversation.
For instance, right now I am in a Super 8 in Galesford, Illinois. Prior to this, I tried to check in to the Holiday Inn Express, but I literally could not find the way inside it. Although it was right next to the freeway exit, the motel was surrounded by a high fence. The whole thing was like some cruel joke.
So when I checked into this hotel, I asked the woman at the counter about it and we had a nice chat about how the zoning board in this town is all crazy and anti-business and won't give people permission to build driveways to their businesses. Am I best friends with the lady at the counter? No. But I did learn something new.
Anyway, the reason I am posting this is to ask people for their advice. Do you ever converse with complete strangers? How do you go about it?