Walking up to a stranger and starting a conversation, part 2

I’ve been thinking about my post about walking up to a stranger and starting a conversation with a stranger. While I’m glad I did it, I’ve noticed something: as each day has gone by since I’ve done it, the more concerned I get about being able to do it again. Was it a one-shot deal? Am I going to crawl back into my cave now? I think what it boils down to is that, yes - if I don’t keep testing myself and putting myself in such a difficult situation, I will crawl back into my cave. At least in my case, I think that this whole being able to talk to strangers thing is a good example of “use it or lose it.”

Because I really enjoyed the experience, despite how difficult it was (and damn, it was…), I think I’m going to set myself a goal. I think doing it once a day would be a bit much; introverts like me do need our rest, after all! Maybe three random stranger conversations a week? That’d be doable, I suppose. A few things that I think are good to keep in mind when considering starting a conversation with a stranger:

• Most likely, if they’re by their lonesome, they’ll like having someone to talk to, even if it’s for a few minutes. We are, after all, social creatures.
• What’s the worst that can happen? Well.. okay, maybe that’s going a bit far. I suppose they could be a dangerous criminal and.. err.. okay, this isn’t helping you (or me), is it? Most likely, the worst that’s going to happen is that they don’t want to talk. Big deal. Say “Have a nice day” and move on. There are always other folks to stalk talk with!
• Don’t over-analyze. Don’t stand back, thinking up a script for the conversation. “I’ll say this.. they’ll most likely say this, so I’ll respond with this, then they’ll probably say….” It won’t work. 99 times out of 100, they’ll break your script with the first thing they say. Then you’re going to be standing there going, uhhh.. what now? Anyway - if you think about it too much, you most likely won’t do it. If you’re like me, anyway.
• Just to reiterate that last one in fewer words: just do it. Pick someone, walk up, and say hi. See where it goes. If it doesn’t work, oh well; try again with someone else, or try on a different day. If it does work, it’ll be great.

Anyone have any more tips on how to make this whole thing a bit easier?