100 questions to ask your grandparents

There is a particular kind of regret that arrives about a year too late. You knew your grandmother grew up somewhere near Liverpool. You knew there was a story about a bicycle. You never asked, and now nobody in the family can fill in the rest.

The obstacle is almost never willingness. It is that "tell me about your life" is an impossible question to answer. It's too big, it sounds like a test, and the honest response to it is a shrug. Specific questions don't have that problem. Ask what a loaf of bread cost in 1958 and you'll get twenty minutes on the shop, the shopkeeper, and the walk there. If it's your own mother or father you're asking, the polished-anecdote problem is different enough that we keep a separate list of questions to ask your parents.

Before you start: four things that make this work

1. 1

   Ask about things, not feelings

   "How did that feel?" tends to get "fine". "What did the kitchen look like?" gets you the stove, the damp washing, and who sat where — and the feeling arrives on its own, inside the detail.

2. 2

   Let silence do some work

   The pause after a question is usually someone deciding whether the real answer is worth telling. Filling it with a follow-up question closes the door you just opened.

3. 3

   Record it, or write it down the same day

   You will not remember it as well as you think. A phone voice memo on the table is enough, and most people forget it's there within a minute.

4. 4

   Ask the same question twice, years apart

   You'll get a different answer, and the difference is often the most interesting part. This is an argument for starting now rather than waiting for a better occasion.

Childhood and home

For a longer run at just this subject — council house, terrace, tenement or prefab, and what's gone from the street since — see questions to ask about a childhood home.

School, work, and National Service

If National Service specifically is what you're after, a dedicated page on it goes further — who was actually called up, when it ended, and why Remembrance Sunday is the wrong day to leave the asking until.

Love, marriage, and friendship

The wider world

The seaside holiday question above is a good one to pull out on its own too — a dedicated page on seaside holiday memories goes further into Blackpool, Butlins, Wakes Week and the first trip abroad.

Family and the things that get lost

Money, food, and making do

Looking back

What to do with the answers

The hard part isn't the asking — it's that the answers end up in a notes app, a voice memo you never play back, and your own memory, which is the least reliable of the three. Six months later there's no record that the conversation happened. The practical side of that — what to record on, and when to write it up — is in how to record your parents' life story.

Some families solve this with a notebook and real discipline. Others record every visit and mean to transcribe it. Both work if you actually do them. The failure mode is always the same: no structure, so it depends on someone remembering to keep it up. And if memory loss is part of the picture, the gentler reminiscence questions for dementia are better ground than this list.

StoryPrompt is one answer to that. We email one of these questions to your parent or grandparent every week, they write back in their own words, and every answer is collected into a typeset book you can download whenever you like, for as long as StoryPrompt runs. Nothing to install, no app, no password — an email and a text box. £25 once, for a year of prompts; the book stays downloadable after the year is over.