How to Ask Strangers What They Care About (Without Scaring Them Off)

Why is it when we meet new people, our way of self-identifying, and our first question to them, is so often about what we do “for a living”? I suppose this is because it’s safe — most of us don’t see such questions as highly personal or invasive. But it also pretty much reduces the short-term likelihood of getting to know this new person well, or even at all in any meaningful way. Which in formal or obligatory settings is probably just what we often want. For those that enjoy it, small talk has its place.

Recently, there have been attempts by meeting and event organizers to craft some questions that are more informative, meaningful, and auspicious for establishing close and valuable relationships. They have to walk a line between being too innocuous to be engaging, and crossing personal boundaries too quickly and non-consensually. Unlike wild creatures, we can’t just sniff out someone we’ve just met and from that know, sensuously and intuitively, whether we want to hang around them or not. While it is to the point, my recent habit of asking new acquaintances “What are you doing that you really care about these days?” is too abrupt and awkward for most. And it often points out that many of us are living automatic lives, on hold for times that offer us the luxury of doing what we really (think we) want to do, and that there is little or no intersection between what we’re doing and what we really care about.

Event organizers call not-too-personal but relationship-opening questions “ice-breakers”. Many of them IMO are just as awkward as my “what do you care about” question — they inquire about personal preferences, happy memories, and to some extent aspirations. The answerer generally struggles with coming up with a response that’s not too personal, but doesn’t sound superficial or trite. As with most questions with people we’re not yet sure we want to associate with (or are pretty sure we don’t want to associate with), there is an enculturated tendency to provide an answer that is palatable to the questioner, whether or not it is true. This makes the whole process annoying, and less than transparent.

So I’ve been looking for some questions I could ask that avoid these problems. The criteria for these questions are, I think:

  1. They elicit honest answers rather than clever, safe or socially acceptable ones.
  2. They are not so personal that they make you hesitant to answer, but are personal enough they tell others something interesting and possibly ‘useful’ (to you both) about you.
  3. They are interesting (and perhaps even self-revelatory) to think about, but don’t (for most people) require an enormous amount of time and energy to ponder to come up with an answer.
  4. They encourage follow-up questions and deeper explorations into the answers and reasons for them.

Here are a few questions that, in the right circumstances, might meet these criteria:

  1. What do you wish you’d learned earlier in your life. Probably best to take turns describing one thing at a time you wish you’d learned, since most of us probably have multiple answers. In my experience this question almost always leads to a discussion of how you came to learn this (a brief story) and why you wish you’d learned it earlier. It’s fine if you never get past the first learning. You might introduce this question gently by saying something like “I’ve just been thinking about how I wish I’d learned earlier in life (eg ‘not to blame or judge people, since I think we’re all struggling to do our best’); ever wished you’d learned something earlier in your life?” It may help to provide your own answer first, to indicate a willingness to move beyond small talk.
  2. Of the people you’ve known in your life but fallen out of touch with, who would you most like to reconnect with, and why? This may require more thought, but again it will inevitably provoke a story and some understanding of what’s important to the answerer. An alternative for those who have no answer to this one might be: Of the people in your community, who would you most like to get to know better, and why?
  3. If you had to choose one written passage of no more than 500 words (a couple of pages) to read out loud that summarizes your worldview or philosophy of life, what would it be? Even better if it’s at hand and can be read our loud — it should only take 3-4 minutes. Now that’s a conversation starter!

If you’ve found other questions that meet the above criteria, I’d love to hear them, especially if you now use them when you meet and engage with new people.

There are probably more suitable questions to use in paid work settings, but since I’m retired (and use questions like those above in settings when those present are all volunteers) I’m not the best one to come up with them.

What I like about these questions, and these criteria, is that they can apply even when the people involved are poles apart socially, culturally or politically. Depending on the circumstances, I wouldn’t be averse to answering the above questions with reference to my current positions on complexity, civilizational collapse, nonduality, and/or whole plant food diets: I think it’s possible (though not easy) to broach these subjects in a non-confrontational, non-preachy way. And since I care so much about these subjects, I suspect that many others, though they may not share my particular views, also care about understanding how the world works, our future, the essence of human nature, and how to live well. The less time we take getting to talk about what we care about, and what we’ve learned, the better.

Image CC0 from the good folks at pixabay.

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