Story Prompts & Questions
The right question turns "how was your day" into a story you will keep for the rest of your life. Here are more than 60 meaningful questions to ask your grandparents and parents about their life, their history, and what they believe. The trick is simple: don't just ask them. Record them.
Ask on paper, lose the person
A written answer saves the facts. A video saves the person: their voice, their face, the pause before the good part, the laugh halfway through. That is the difference between a document and a memory you can sit with.
Pick a few questions, not all of them. Sit down with your parent or grandparent, press record on your phone, and let them talk. The questions below are grouped by theme so you can follow whatever they are in the mood to share. Dear Family turns these same prompts into guided, one-tap video recordings that save straight to your private family library.
The questions
Start anywhere. The best ones are open-ended, so they invite a story instead of a yes or no.
Capture it well
You don't need a studio. You need a phone, a quiet room, and a little patience.
Find a quiet, well-lit spot and sit across from each other. Prop the phone at eye level so their face fills the frame, and check that you can hear them clearly before you start.
Give them a single prompt and then stop talking. Silence is fine. The best stories often come right after a pause, once they have had a moment to remember.
Don't rush them back on track. If a question about their first job turns into a story about a coworker they loved, follow it. That tangent is usually the gold.
The simplest follow-ups draw out the most. Try "what happened next," "how did that feel," or "who else was there." You are drawing out the story, not interviewing for facts.
Save each recording somewhere permanent and come back for more another day. A few questions at a time, over months, becomes a library your family will treasure for generations. This is exactly what Dear Family is built to do.
The easiest way to record
Dear Family turns questions like these into built-in prompts. Your parent or grandparent picks one, taps record, and answers on video. No blank page, no wondering what to ask next.
Every answer is saved as video, so you keep the real person, not a typed summary. Years from now your family hears exactly how they told it.
Recordings land in one private Family Legacy Library the whole family can add to and watch forever. Ask a few questions today, a few more next month, and watch it fill in.
$99/year at launch, and the whole family can record and contribute, not just one person.
Want to go beyond questions?
Recording your family's answers is the start of something bigger: an ethical will, the values and wisdom you pass on instead of the things you leave behind. Learn what an ethical will is and why it matters.
Common questions
The best questions invite stories rather than yes or no answers. Ask about their childhood, how the family began, how they met their spouse, the hardest things they lived through, and the lessons they learned. This page has more than 60, grouped by theme.
Yes. Writing captures the facts, but recording on video captures their actual voice, their face, and the way they tell the story. Dear Family is built to record these answers and keep them in one private family library forever.
Use a phone, or an app made for it like Dear Family. Ask one question at a time, keep the camera steady at eye level, and let them talk without interrupting. Guided prompts make it easy to know what to ask next.
Only a few. It is better to go deep on a handful than to rush a long list. You can record more over many short sessions, and it all adds up over time.
Capture them in the person's own voice on video, then keep them somewhere permanent and private. Dear Family stores every recording in a private Family Legacy Library your whole family can watch for generations.
There's no right moment
Pick one question. Sit down with them this week and press record. It is the kind of thing no one ever regrets doing, and many wish they had done sooner.
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