Grandparents hold the oldest stories in the family: the ones that reach back furthest, the ones no one else can tell. And they’re often happiest to share them with a grandchild who simply asks. Here are the questions worth asking your grandparents, grouped by theme, plus a gentle way to make sure the answers last.
The best question to start with: “What were you like when you were my age?” It’s easy to answer, it surprises them that you asked, and it opens almost every other door: childhood, dreams, the world as it was.
These pair with our pillar list, questions to ask aging parents. The ones here lean into what makes grandparents special: deeper roots, a longer view, and a soft spot for the grandchildren.
Their childhood and the world back then
- Where did you grow up, and what was your home like?
- What did you do for fun before TV and phones?
- What’s something that was normal then that would shock kids today?
- Who was your best friend as a child? Do you remember a day with them?
- What did a loaf of bread, or a movie ticket, cost?
Their parents and grandparents (our roots)
- What were your parents like? What did they do?
- Did you know your grandparents? What do you remember about them?
- Where did our family come from before here?
- Is there a family story that got passed down to you?
- What language or traditions did the family keep?
Love, family, and the big moments
- How did you meet Grandma/Grandpa? What was your first impression?
- What do you remember about the day my parent was born?
- What was the proudest moment of your life?
- What was the hardest year, and how did you get through it?
For the grandchildren
- What do you want us, the grandkids, to remember about you?
- What’s the best advice your own grandparent gave you?
- What did you wish you’d done more of? Less of?
- If you could leave us one piece of advice, what would it be?
How to ask (so they actually open up)
- One at a time. A list feels like a quiz. Ask one, listen, and let “and then what happened?” do the rest.
- Record it. A grandparent’s voice, the accent, the laugh, is the part you’ll treasure most. A phone is enough to start.
- Keep it short and warm. Fifteen minutes over tea beats a formal interview. Come back another day.
- Let them skip anything. Some doors open later, or not at all. That’s okay.
MyDear guides your grandparent through their life story by voice, gently, ten minutes at a time, and turns it into a real book the whole family keeps. $45, no subscription.
A real printed book · no subscription · their words stay private.
Don’t let the answers fade
The hard truth behind every one of these questions is that they have an expiry date. The good news is that capturing the answers has never been easier, whether you record them yourself (here’s how to record a grandparent’s life story) or let a guided tool do the asking and turn it into a book. Ask while you can. You will never regret having done it.