Questions about your parents' bravest moments
5 questions
Most lives have a few moments of unexpected bravery — a chance taken, a trip booked on impulse, a decision that should have terrified them more than it did. These questions are about those moments. The ones that, on a good day, your parents will laugh about and shake their head at.
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Adventure
- 01
What's the bravest thing you've ever done?
Ask if it felt brave in the moment, or only in hindsight.
Have us text this one → - 02
What's the longest journey you've ever taken — and what did it teach you?
Ask what they remember most clearly from that trip — a face, a meal, a moment.
Have us text this one → - 03
Have you ever done something that scared you and been glad you did?
Ask what they would have lost if they hadn't.
Have us text this one → - 04
What's a place you visited once and have always wanted to return to?
Ask what would make them go back if they had the chance.
Have us text this one → - 05
Did you ever take a chance that could have gone really wrong?
Ask what they were thinking the whole time it was unfolding.
Have us text this one →
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.
Free printable
Get this list as a beautifully printable PDF
All 168questions, arranged by theme — print it, bring it to Sunday dinner, or keep it by the phone. We'll email it to you free.
No spam — a few question ideas and a reminder before the next holiday. Unsubscribe anytime.