Questions about their school years

8 questions

School is where most people first discovered what they were good at, who they wanted to be near, and what they were going to spend the next several decades trying to outrun. These questions are about those years. They tend to produce specific, sensory answers — a classroom, a teacher, the friend who walked them home — and they're a soft place to start a longer conversation.

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School & learning

01
What was your first day of school like?
Ask if they remember who was there with them, and how they felt walking in.
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02
Was there a teacher who saw something in you that nobody else did?
Ask if they ever told them what they meant to them.
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03
What did you love about school, and what made you dread it?
Ask if the things they loved are still part of who they are.
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04
Did you go to college? What did that decision mean for the rest of your life?
Ask what they'd say to a younger person facing the same choice now.
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05
What did you learn outside the classroom that ended up mattering more?
Ask who taught them that, even if they didn't know they were teaching.
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06
Were you a good student? Did anyone's expectations of you weigh on you?
Ask if those expectations turned out to be a help or a burden.
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07
Tell me about a friend you made at school. Are they still in your life?
Ask what brought them together — and what would have happened if they hadn't met.
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08
What's something you learned in school that you still use, and something you never used at all?
Ask if school ever taught them anything that wasn't on a test.
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How to actually ask these

·Pick three or four. Trying to ask all of them in one sitting will exhaust you both. The best conversations come from one question that opens up into twenty minutes of unrelated stories.
·Don't correct or argue. If their memory of an event doesn't match yours, that's a separate conversation. Right now you're collecting their version.
·Write down what they say while it's fresh — or record it. Phones are good for this. You don't need anything fancier.
·If asking face-to-face feels like too much pressure — for either of you — consider letting our service text them one question every few days. Many people open up more easily over text than across a kitchen table.