The Art of Asking Questions

About a year ago, my friends and I started keeping a list of questions to ask people.

There is no real theme to it. Some are personal. Some are uncomfortable. Some are philosophical. Others are so absurd that there is almost no reasonable explanation for why anyone would need to answer them.

That is partly the point.

I have become fascinated by what happens when you ask someone a question they have never prepared themselves to answer.

Most of the questions we ask one another are predictable. What do you do? Where are you from? What are your plans? We become very good at answering them. Eventually, we can move through entire conversations exchanging information about ourselves without having to think very much at all.

But ask someone something completely unexpected and, for a moment, there is no rehearsed answer available.

You get to watch them think.

That has become one of my favorite things.

It is interesting to see where someone’s mind goes when there is no obvious direction for it to take. Two people can hear the exact same question and interpret it completely differently. One person finds a loophole. Another takes it literally. Someone else somehow turns a ridiculous hypothetical into a philosophical discussion.

And sometimes the question stops being a question altogether.

Someone gives an answer, someone else adds a detail, and suddenly we are ten minutes deep into an entirely fictional reality that did not exist before the question was asked. New rules are established. Hypothetical consequences need to be considered. Everyone becomes strangely invested in defending decisions about a world we collectively invented five minutes ago.

I love that.

There is something freeing about being given permission to think about something completely unnecessary. So much of adult thought is directed toward usefulness. We think because something needs to be solved, decided, understood, planned, or accomplished.

A ridiculous question asks nothing productive of us. It gives the mind somewhere to go simply because it can.

And there is a strange amount you can learn about someone in the process.

Not necessarily from the answer itself, but from how they arrive there. What do they take seriously? What makes them laugh? Where does their imagination go first? What assumptions do they immediately make? How far are they willing to follow an idea once it becomes completely ridiculous?

The reaction can be as interesting as the response.

I also wonder how often anyone asks us to think this way.

There are entire directions our minds may never travel simply because nothing in ordinary life requires us to go there. Then someone asks you a completely unnecessary question and suddenly you are considering an idea you have never had any reason to consider before.

Maybe that is part of the art of asking questions.

A good question does not only uncover something that was already inside another person. Sometimes it creates something that was not there at all.

A conversation. An idea. A fictional universe. A completely absurd argument that everyone suddenly cares deeply about.

The question is simply the opening.

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Is Boredom a Conditioned Perspective?