Should we ask about the past?

Ask directly about the past if you’re interested in learning about a specific time—a particular point in history like the 1960s, or the viewpoints of people of a certain age like 20-something—because the “when” is a critical feature of what you are interested exploring through your question. There are countless questions that have “when” as a critical feature. For example: What was it like for you in the 1960s? What were 21st birthday parties like for you and your friends? We are pointing directly to a point in our guest’s history, and asking to know more about that time.

But those are obvious times to ask about the past. There are many questions which are asked about the past which aren’t actually about a specific time. They’re questions about something else… and because everything has happened in the past, the “when” part is irrelevant to the question. We may think that we can explore interesting things by asking about the past, but it only distracts our guest; It only adds extra context that we have to say, while not being meaningful.

Which of these questions is more likely to get you into a fun and engaging conversation:

When did you learn to fly a plane?
What made you want to learn to fly?

When did you know they were the one you wanted to spend your life with?
How did you know they were the one…?

When did you learn to speak [a foreign language you know they speak]?
Why did you learn…

Someone will always tell you the when as part of answering what, how or why. They have to talk about the past, they’ll have to give you context, and that will be some “when” information.

Then you can bring “when” in as context to help your guest get their thinking going. Some people (who often describe themselves as quiet types or introverts) have trouble answering questions on the fly. But, everyone loves questions like the following…

Wow, it sounds like you’ve been flying planes a really long time. You must have started when you were really young. What made you want to learn to fly?

Congratulations on such a long relationship. I’m fascinated by how you made the Big Decision in the beginning of your relationship. How did you know they were the one?

I’m interested in how age relates to learning languages. I understand that the earlier people learn their second language, the more languages they go on to learn. Was [language] your second language? Why did you want to learn that language?

Until next time, stay curious!

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