Funny Questions to Ask Your Grandparents
These are for the grandkid who would rather hear about the day Grandpa got sent home from school than fill in a family tree, and for the parent trying to get the kids and the grandparents talking over dinner. The 51 questions follow the way the stories tend to come out: Trouble first, then Fads, Romance, Family, Nowadays and What if. Pick three or four for a visit and, if they agree to it, leave a phone recording, because the best answer is usually the one that starts with 'well, I should not tell you this.'
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The questions
Each question, and why to ask it
Trouble
What is the most trouble you ever got into at school, and what happened next?
Why ask it
School trouble makes a safe opener, since nobody is left to hand out the detention. Ask for the teacher's name: a grandparent who has lost the year usually still has the name, and the look on that teacher's face.
What were you allowed to do at ten that would get me grounded for a month?
Why ask it
Riding in the back of a truck, playing on a construction site and staying out until the streetlights came on are the kind of thing to expect. Look delighted and not horrified, or the next story arrives with the good parts removed.
What embarrassing moment did you think you would never live down, and how long did it take?
Why ask it
The audience is the punchline, so ask who was watching: a classroom, a dance hall, a future mother-in-law. Take the story they choose to give, even if you know there is a better one, because an embarrassment they are not yet laughing at is theirs to keep.
Who taught you to drive, and what did you hit?
Why ask it
Driving lessons from a parent tend to be remembered word for word, including the words. A grandparent who never drove usually has a bicycle, a tractor or a terrifying ride in a passenger seat to tell you about instead.
Which brother, sister or cousin got you blamed for something they did?
Why ask it
An old injustice gets told with fresh outrage sixty years later, which is the fun of it. If the guilty party is still living, phone them afterward for the defense. If they have died, the story may turn fond partway through, and that is fine.
What did you break, hide or bury so your parents would never find out?
Why ask it
Three verbs give three chances at a memory, which helps on a day when stories are slow to come. The follow-up writes itself: did the parents find out, and how long did it take them?
What prank did you pull that you are still a little proud of?
Why ask it
The words 'a little proud' give permission to brag. Find out who the target was and whether they ever got even, because a prank with a sequel is two stories.
Which friend did your mother call a bad influence, and was she right?
Why ask it
Get the friend's name and one thing the two of them did together. Quite often the grandparent admits, with some pride, that they were the bad influence and the friend took the blame.
What is the dumbest dare you ever said yes to?
Why ask it
Dares come with a location, an audience and usually an injury, so one answer can run five minutes. If young kids are listening, add that nobody at this table is to try it.
Fads
What piece of clothing did you beg or save for, and how does it look in the photos now?
Why ask it
The item dates them to the year, whether it was a pair of bell-bottoms or a jacket that cost three weeks' pay. Ask to see the photo, and say something nice about it before anyone laughs.
Which hairstyle took the most work, and what did you put in it to keep it there?
Why ask it
Hair stories come with equipment: rollers slept in, a clothes iron, a product with a smell they can still describe. With a grandfather, try the sideburns or the mustache somebody talked him out of.
What fad went around your school that makes no sense to you now?
Why ask it
They end up explaining the rules of something that never had any, which is where the laughs are. Have a current craze of your own ready, because they will ask, and yours will sound just as odd said out loud.
Which singer or movie star did you have a crush on, and was there a poster?
Why ask it
Look the star up on your phone and hold the screen where they can see it, since a face often brings back more than a name does. With both grandparents at the table, ask each what they thought of the other's pick.
What slang did you use that drove your parents up the wall?
Why ask it
Ask them to put it in a sentence, with the voice, and then to do their mother's or father's reply. If they have agreed to be recorded, this is the one to have the phone running for: a grandparent in full teenage slang is the clip a family replays.
What did your parents say was ruining your generation?
Why ask it
Whatever it was, rock and roll, comic books, long hair, keep hold of the answer. It comes in handy a few questions later, when they start on what phones are doing to yours.
What food counted as fancy when you were young?
Why ask it
The answer depends a great deal on where and when they grew up, and it can be as modest as fruit from a can or a restaurant with cloth napkins. Offer to make the dish together exactly as it was served, and eat the result.
Romance
What is the worst date you ever sat through, and how did it end?
Why ask it
A bad date is easier to talk about than a romance, and it can be told without naming anyone. If the bad date turns out to have been your other grandparent, you have the best story of the visit.
Who was your first crush, and did they ever find out?
Why ask it
A first crush tends to come back with a full name and the desk they sat at. With the other grandparent listening, ask whether they have heard this name before, and how many times.
What line did people use to ask someone out back then, and did any of them work on you?
Why ask it
Have them deliver the line the way it was said. Younger kids enjoy this more than you would guess, mostly because a grandparent being asked out is news to them.
What rules did your parents set about dating, and how did you get around them?
Why ask it
The second half is the real question, so wait for it even when the first answer is a prim one. Curfews, chaperones and a little brother sent along as a spy all had workarounds.
What did you honestly think of Grandpa (or Grandma) the first time you saw them?
Why ask it
With both in the room, have one answer while the other covers their ears, then swap. If the other grandparent has died, the question is often still welcome, but let them choose how light to keep it.
Who chased whom, and does the other one agree with that?
Why ask it
It needs both grandparents present, because the disagreement is the entertainment. Do not referee. Two versions that have differed for fifty years are not going to be settled over dessert.
What did one of you do to impress the other that completely backfired?
Why ask it
Ask what the other one did at the time: laughed, pretended not to notice, or nearly called the whole thing off. A borrowed car or a meal well beyond the cook's skill is usually in there somewhere.
What happened at your wedding that never made it into the photo album?
Why ask it
Bring the album out afterward and have them point to the moment just before it happened. Anyone at the table who was a guest that day makes a good second witness.
What was the first meal one of you cooked for the other, and could you eat it?
Why ask it
Many couples keep a newlywed cooking disaster polished and ready, so you may get the well-worn version. Ask what they ate instead that night, which is the detail the polished version leaves out.
What habit of theirs did you only discover after the wedding?
Why ask it
Keep it affectionate by asking the reverse right away: which of their own habits did the other one have to put up with? Snoring and the toothpaste cap are the standard complaints, and the better answers are stranger, like a fixed way of folding a road map.
Family
What is the worst trouble my mom (or dad) ever got into, and what did you do about it?
Why ask it
Best asked with your parent at the table and unable to leave. Agree on one rule first: nothing said here can be used to ground anyone after the fact, in either generation.
What do you let us grandkids do at your house that my mom (or dad) was never allowed to?
Why ask it
Plenty of grandparents know exactly what they are doing with the second dessert and the late bedtime, and enjoy saying so. Watch your parent's face during the answer, then ask whether the old rules were really as strict as your parent has always claimed.
What did you walk in on when the house had gone suspiciously quiet?
Why ask it
Flour, scissors, a pet and a marker are the usual ingredients. Find out whether they laughed or shouted, since plenty of grandparents admit to shouting in the room and laughing in the hallway.
What did my mom (or dad) flatly refuse to eat, wear or do, no matter what you tried?
Why ask it
You will probably recognize the stubbornness. Get the full list of bribes and threats that were attempted, then check whether your parent has since used the same ones on you.
What did one of your kids say when they were tiny that the family still repeats?
Why ask it
A mispronounced word or a loud remark in a quiet place can turn into family vocabulary, and you may have been using it without knowing where it came from. Write the phrase down with who said it and how old they were.
What is the funniest thing I said or did when I was too small to remember it?
Why ask it
Here the grandchild becomes the subject, which small kids love and teenagers pretend not to. With several grandchildren in the room, ask for one story each, so nobody is left out and nobody is singled out.
What phase did my parent go through that you could not wait to see the end of?
Why ask it
If a photo of the phase exists, your parent knows exactly where it is and will suddenly need to be in another room. Ask how long it lasted and what finally ended it.
What did my parent bring home that you did not want in the house?
Why ask it
Left open on purpose: it might be a stray dog, a jar of frogs, a drum kit or a boyfriend. Then ask how long it stayed, and who ended up feeding it.
What white lie did you tell your kids just to get some peace?
Why ask it
Ask at what age your parent worked it out, and whether you have been told the same one. The well-known versions are the television that needs a rest and the ice cream truck that only plays music once it has sold out.
Which family trip went the most wrong, and whose fault was it?
Why ask it
Anyone who was on that trip gets to object, and the argument over whose fault it was is the real answer. Give the grandparent the last word, since they were probably the one driving.
Nowadays
What does your phone do that you never asked it to?
Why ask it
It starts as a complaint and ends as a demonstration, so have them show you on the phone itself. Fix the thing afterward if you can; it is a fair price for the stories.
What do people happily pay for now that you cannot believe anyone pays for?
Why ask it
Ask what the same money bought when they were your age, and let them enjoy the look on your face. Bottled water and jeans sold with the holes already in them tend to get a mention.
Which of today's fashions looks ridiculous to you, and which one do you secretly like?
Why ask it
The second half stops this from turning into a list of grievances. If the ridiculous one is something you are wearing, take it well: you asked.
What word or phrase do people my age say that you cannot make sense of?
Why ask it
Turn it into a guessing round: you say the word, they guess the meaning, and the wrongest guess wins. Face them and say each word clearly, because slang is hard to catch when hearing is not what it was.
What do you think of the music I listen to? Be honest.
Why ask it
Play one song, not a playlist, at a volume they choose, and ask for a score out of ten. Then they pick one of theirs and you score it, kindly.
Which modern invention do you think is overrated, and which one would you refuse to give up?
Why ask it
Listen for the gadget they are more attached to than they let on: the dishwasher, the remote, video calls with the grandkids. The overrated one usually gets a speech, so settle in.
What can you get away with at your age that you never could at mine?
Why ask it
Here being old is the advantage, and grandparents tend to answer with relish: leaving parties early, napping in company, telling people what they think. It is a welcome change after a long run of questions about the past.
What if
If you could bring back one store, candy or TV show that has disappeared, which would it be?
Why ask it
Naming three kinds of thing makes it easier to land on one. Search for the candy or the theme song on your phone while they talk, since some of these turn out to be still on sale or one click away.
If you and I swapped lives for a day, what would you do with mine?
Why ask it
A small child can answer the other half on the spot: a day as Grandpa usually means driving the car and eating every cookie in the house. What the grandparent picks is often something they miss, like running flat out or staying up all night, so ask for a story about it.
If someone made a movie about your life, who would play you, and what would it be called?
Why ask it
The title is the better half, so do not let them skip it. For a grandparent who does not follow current actors, a star from any decade counts, and the family can cast the supporting roles.
If you could have taken one of today's gadgets back to when you were sixteen, which one, and what trouble would it have caused?
Why ask it
This joins the two ends of the conversation, their teens and your world. A phone at a school dance is the sort of answer that gets the whole table inventing consequences.
If you could pass one silly law that everyone had to obey, what would it be?
Why ask it
The word 'silly' has a job: it keeps the answer on slow drivers and loud chewing and away from real politics at a holiday table. If it drifts there anyway, ask for a second, sillier law.
If you had to go on a talent show tonight, what would your act be?
Why ask it
A whistled tune, a card trick or a poem learned at school all count as an act. Ask for a short demonstration only if they seem eager, and clap either way.
If our family had a motto based on how we really behave, what would it be?
Why ask it
A grandparent has watched the family longer than anyone, so the motto tends to be accurate and a little rude. Vote on the best one and write it inside the next birthday card.
What would the sixteen-year-old you be most shocked to learn about you now?
Why ask it
Keep it for last, because it is funny and usually ends somewhere warm without anyone being asked to be serious. Be ready to answer it about yourself, since they often turn it around.
How to get the funny stories out of a grandparent
Practical guidance for the conversation itself
Before you ask anything
Three or four questions is a whole visit
One good question can fill twenty minutes once the cousins start adding details. Choose a few from different groups before you arrive, and treat the rest of the page as spare. A grandparent who is read the whole list from top to bottom has been handed a form to fill in.
Open with Trouble
The mischief questions come first on the page for a reason. Each asks for a single scene from long ago, the kind of story that tends to come easily, and together they tell your grandparent what sort of conversation this is: one where they get to be the kid who misbehaved, and nobody is checking dates.
Bring a story of your own to trade
Laughs go further when they run both ways. After the dare question, admit to a dare of your own. After the question about words they cannot make sense of, teach them one. A grandchild who only collects stories is doing homework, and one who swaps them is having a conversation.
Admire the jacket before you laugh at the collar
Teasing is part of the fun, and a lot of grandparents give as good as they get. Still, lead with interest. Say the jacket looks sharp, then ask what on earth is going on with the collar. If a tease gets a flat look, apologize in one sentence and move to the next question.
Where and how to ask
At a holiday table
Give each grandchild one question to ask, written on a slip under their plate, and let the youngest go first. One question per course is plenty. Keep Romance and Family for when the parents are sitting down and cannot escape to the kitchen.
When a parent is prompting younger kids
A small child will read the question out and then look at the ceiling. Whisper the follow-up to them: 'Ask who told on her.' The What if group suits the youngest best, because they can answer the same question themselves right afterward.
When Grandma and Grandpa are both there
Ask one, then ask the other whether that is how it happened. The Romance group is built for this. Share the questions out evenly, so the quieter grandparent is not left as the audience for the talkative one.
On a phone or video call
Send the question a day ahead in a message, so there is time to think and to dig out a photo. On the call, ask one question and then stop talking. A delay on the line makes interruptions worse, and a pause that feels long to you may be the story being found.
Hearing, memory and tender spots
Set the room up for hearing
Turn off the television and any music, sit where your face is in the light, and ask the question once, slowly, without shouting. If you have to repeat it, try changing the wording before the volume. A crowded table is a hard place to follow a conversation, so a grandparent who struggles to hear may do better with two grandchildren on the couch afterward. Ask them what works, because they know.
Never turn a story into a quiz
If a name, a year or a town will not come, say it does not matter and go on with the story. Do not correct a detail that differs from the last telling, and do not look to another adult for the right version. On this page the true answer and the funny answer are allowed to be different.
Hearing the same story again
A story you have heard five times is still the one they want to tell. Ask about a part you have never asked about: what they were wearing, who else was there, what happened the next morning. If memory loss is a real concern in your family, ask the relative who spends the most time with them which subjects go well and which to leave alone.
When a funny question lands on a sad place
A question about a brother, a wedding or a family trip can reach someone who has died. Do not hurry past it or apologize for asking. Give it a moment, say something like 'he sounds like fun,' and let them decide whether to stay there or go back to the laughing. Quite often they go back on their own, with a better story.
Stop while they are still enjoying it
Shorter answers, a glance at the clock or a story that trails off mean the visit has had enough questions. Thank them, say which story was your favorite, and tell them you want another one next time. That gives them something to look forward to and time to choose it.
Recording the answers
Ask first, and say who will hear it
Before you record, ask, and say plainly that it is for the family. Some grandparents tell a wilder story with the phone off, and that is their call. If a story is about someone else in the house, such as your parent at fifteen, ask that person too.
Keep the phone out of the way
A voice memo with the phone face down on the table is less off-putting than a camera held up between you. Put it nearer to them than to you, and run a ten-second test first if the room is noisy. Video earns its place for anything with a demonstration: the slang, the pick-up line, the talent show act.
Name the file the same day
Rename the recording with their name, the date and two words about the story before you leave, and send a copy to one other relative. A file left as 'New Recording 14' is hard to find again and easy to lose when a phone is replaced.
Nothing gets posted without a yes
A grandparent trying out your slang is very funny and very shareable. It is also theirs. Show them the clip, ask whether it can go in the family chat, and treat anything wider than that as a separate question.