50+ questions to know your grandparents before it's too late

My grandmother made the best chicken and dumplings I've ever tasted. Thick, doughy dumplings that fell apart when you touched them. She made them every Sunday for forty years.

I don't have the recipe.

She died when I was twenty-three, and I'd eaten those dumplings hundreds of times without once asking her how she made them. I never asked where she learned it, either. Was it her mother's recipe? Did she figure it out on her own after she got married? Did she change it over the years?

I'll never know. And that's just a recipe. Think about everything else I didn't ask.

If you still have grandparents alive, you're holding something you can't get back once it's gone. These questions to know your grandparents aren't just conversation starters. They're a way to pull out the real stories, the ones that won't exist anywhere else once your grandparents are gone. No one else knows what your grandfather felt on his wedding day. No one else remembers what your grandmother's childhood kitchen smelled like.

This is your window. It gets smaller every day.

Why these conversations keep getting postponed

Here's the thing nobody tells you: asking your grandparents about their lives feels awkward at first. You see them at holidays and family dinners, and the conversation stays on the surface. How's school? How's work? Did you see what the weather's doing this week?

It's not that you don't care. It's that you don't know how to shift from small talk into something real without it feeling forced or, worse, like you're implying they won't be around much longer.

So you tell yourself you'll do it next time. Next visit. Next holiday. And then one day there is no next time.

The honest truth is that your grandparents probably want to tell you these things. Most older people are waiting to be asked. They don't want to bore you. They don't want to be the grandparent who corners you with stories you didn't ask for. But if you ask? If you sit down and say, "Grandma, what were you like at my age?" — most of them will light up.

You just have to start.

Their childhood and growing up

These questions get at who your grandparents were before they were your grandparents. Before they were parents. Before they were adults with responsibilities. They were kids once, with fears and crushes and bad ideas, and those stories are usually the ones they tell best.

1. Where did you grow up, and what did the house look like?
2. Did you share a bedroom? With who?
3. What did your family eat for dinner on a regular weeknight?
4. What got you in trouble as a kid?
5. Who was your best friend growing up, and what happened to them?
6. What's a smell that takes you right back to childhood?
7. Were you close with your own grandparents?
8. What were you afraid of as a kid?
9. What was your school like? How did you get there?
10. Did you have a teacher who made a real difference for you?
11. What did you do on summer days when there was nothing planned?
12. What's something your parents were strict about that seems funny now?
13. Did your family go to church? What do you remember about it?
14. What was the first time you realized your family didn't have much money, or did have more than others?

The childhood questions work well as a starting point because they're low-pressure. Your grandparents aren't being asked to reflect on regrets or losses yet. They're just remembering being ten years old, and that usually brings out stories you never expected.

Their love story

This might be the most important category, and it's the one most people never ask about. Your grandparents' relationship is the reason you exist, and you probably know almost nothing about how it actually started.

15. How did you and Grandma/Grandpa meet?
16. What did you notice about them first?
17. What was your first date? Where did you go?
18. When did you know this was the person you wanted to marry?
19. Did anyone in your family disapprove? What happened?
20. What was your wedding day like? What do you actually remember about it?
21. Where did you live when you first got married?
22. What was the hardest year of your marriage, and what got you through it?
23. What's something you had to learn about each other the hard way?
24. What did you fight about most?
25. How did you handle money together?
26. What's the funniest thing that ever happened between you two?
27. What's the most romantic thing your spouse ever did, even if it was small?
28. If you could relive one day with them, which day would you pick?

If your grandparent has lost their spouse, these questions can bring up grief, so read the room. But in my experience, most people love talking about the person they loved. It keeps them present. Just be ready to listen and don't rush past the quiet moments.

For more on asking meaningful questions of your parents, we put together a similar guide.

Their work life and money

Your grandparents' relationship with work was probably very different from yours. They might have stayed at one company for thirty years. They might have worked a job they hated because that's just what you did. Either way, there are stories in there.

29. What was your first real job?
30. How did you end up in your career? Was it what you wanted, or what was available?
31. What did you get paid at your first job, and what could that buy?
32. Did you ever want to quit and do something else entirely?
33. What was your boss like at the job you had the longest?
34. What's a skill you learned at work that had nothing to do with the actual job?
35. Did you ever lose a job? What happened?
36. What did retirement feel like on the first day?
37. Were there opportunities you missed because of money, or because of the times you lived in?
38. What's the best financial decision you ever made?
39. What's a money mistake you want me to avoid?

These questions often lead to stories about class, ambition, and sacrifice. Your grandfather might tell you about walking away from a promotion because it meant moving away from family. Your grandmother might tell you about the job she wasn't allowed to have because of the era she lived in. These are the details that put a personal history in context.

Their regrets and wisdom

This is where the conversation gets real. Not every grandparent will want to go here, and that's fine. But if they do, these answers tend to be the ones you remember for the rest of your life.

40. What's something you wish you'd done differently?
41. Is there a relationship you wish you'd handled better?
42. What's the best piece of advice anyone ever gave you?
43. What do you know now that you wish you'd known at my age?
44. What did you worry about that turned out not to matter?
45. What's something you're proud of that most people don't know about?
46. Was there a moment that changed the direction of your life?
47. What do you think our family does well? What do you wish we did differently?
48. What's a belief you held strongly when you were young that you've changed your mind about?
49. If you could tell your twenty-year-old self one thing, what would it be?

Don't push if they don't want to answer something. Just move on. You can always come back to it another day. The point isn't to interrogate them. It's to let them know you're genuinely interested in what they think and what they've learned.

The small details that disappear first

Here's what surprises people about grief: it's not the big moments you forget first. It's the small stuff. The sound of their laugh. The way they stirred their coffee. The phrase they always said when they answered the phone. Those details feel so permanent that you don't think to write them down, and then one day you can't quite remember anymore.

50. How do you take your coffee or tea?
51. What's a phrase or saying you use all the time?
52. What do you do first thing in the morning?
53. What's your favorite thing to cook, and who taught you?
54. What song makes you happy when you hear it?
55. What do you watch on TV when no one else is choosing?
56. What's in your pockets right now, or what do you always carry?
57. Is there a place you go when you want to be alone?
58. What book have you read more than once?
59. What's the most ordinary thing in your day that you actually enjoy?

These questions might seem trivial compared to the big life ones. They're not. When you're sitting in your kitchen ten years from now, trying to remember your grandmother, it won't be the year she was born that you reach for. It'll be the way she hummed while she did the dishes. Record the small things. You'll be glad you did.

If you want practical tips for how to actually record these conversations, we wrote a whole guide on that.

How to actually start the conversation

Knowing the right questions is only half of it. You need to get past the initial awkwardness of sitting down and saying, "I want to ask you about your life." Here's what works.

Start with an object. Pick up a photo from their shelf. Ask about the person in it. "Who is this? When was this taken?" A physical object gives you both something to look at, which takes the pressure off eye contact and makes the whole thing feel less like an interview.

Record it, but ask first. Your phone is good enough. Just say, "Do you mind if I record this? I want to remember it." Most grandparents are touched that you'd want to. If they say no, respect that and just take notes after.

Don't do all fifty questions in one sitting. Spread them out. Five questions over Sunday dinner. A few more next time you visit. Let the conversations build. Some of the best stories come out the second or third time, once they've had time to remember things they forgot about.

Bring food. This is not a joke. Sitting across from someone at a table with coffee and something to eat is the most natural conversation setting there is. It gives you both something to do with your hands, and it signals that there's no rush.

Ask follow-up questions. The real stories are usually one question deeper. If your grandfather says he met your grandmother at a dance, ask what song was playing. Ask what she was wearing. Ask if he was nervous. The details are where the story lives.

If you want to see how one family turned these conversations into something lasting, it's worth reading.

The window is open right now

I want to be direct with you. If you have a living grandparent and you haven't had these conversations yet, your window is open right now. Not next month. Not next holiday season. Right now.

I'm not saying this to scare you. I'm saying it because I waited, and I lost things I can never get back. Not just the recipe for chicken and dumplings. I lost the sound of my grandmother's voice telling me about her life. I lost the chance to know what she was afraid of, what she dreamed about, what she'd do differently. Those stories died with her because nobody thought to ask.

You don't need a formal sit-down. You don't need a professional recorder or a list of a hundred questions. You just need to pick up the phone, or sit down next to them at the next family gathering, and ask one question that goes a little deeper than the weather.

That's it. One question. And then another. And then another.

At When I Die Files, we help families keep these stories, wishes, and memories in one place so nothing gets lost. Because the conversations are only the beginning. What matters is making sure they last.