Seven Tips for Making Good Conversation with a Stranger.
happiness-project.com
happiness-project.com
As much I'd like to say that these tips should be common sense, I have begun to recognize that for many people, social skills need to be practiced.
I'd like to add a Tip 0: Be brave. Recognize that both parties feel an unease and that ultimately someone has to make the first move. I promise you will be happy it was you.
If I could do it, I would force every fellow hacker to work for a month as a bouncer at a night club. Get yelled at, get cursed out, get pushed and shoved, get a thicker skin and some street sense.
You will notice that cocky business types[1] and jocks have something in common; they're infallible to themselves. However wrong they are, they speak with bone-headed authority. Now imagine if knowledgeable people were able to push their wisdom with such authority? Develop a fierce fighter, go-getter attitude and you will live a full richer life. Introspection is good when you're still developing your moral system or reflecting on, well, your beliefs. But once you have something you're convinced of, go out there and preach it.
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[1] I don't want to generalize the "business types"; not all suits are alike. A good chunk of them are push-overs who speak with a script and you can easily run them over. Others are brown-noses yes-men; slimey, very slimey, and best kept away. The type I have in mind are your typical, successful lead salesmen. Yeah, those guys, snap them out of their sales pitch by disqualifying yourself as a potential buyer, then twist the discussion and try to "flip them" (i.e. get them to work for you, or talk to them as a peer and talk shop, etc.) those guys are very interesting.
..... ahem
EDIT: besides the flippant humour of the remark I was trying to make a point of gender identities and social profiles when it comes to interaction. It can be surprisingly easy to pick out the "Alpha" and those more subservient or devious when watching a conversation. I wouldn't be surprised at all if speech conventions had a very strict social hierarchy attributed to meaningful measures such as confidence and deviousness.
I like your Tip 0. Sometimes the other person seems to be intentionally hanging you out to dry, but they're really thinking, "Gosh, at least this guy is trying to make conversation. I'm just standing here like an idiot, not helping at all."
Perhaps they don't have "the skills" because they don't think they need them. Spending 10 minutes of one's life chit-chatting with a complete stranger feels like a waste of time to me.
Granted, the probability any of the above happening is quite low, but just having a chat with someone when you're, say, waiting for a bus is not going to waste your time. You don't have to actively seek out strangers to talk to.
BTW, when it comes to social skills, I give myself 1 out of 10.