Questions to Ask Your Grandchildren, Toddler to Teen
For grandparents who want more than a one word answer. These 20 questions move from easy openers you can use with a six year old to the searching ones that work with a teenager or a grown grandchild.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
What is the best thing that has happened since I last saw you?
It is small enough that a shy six year old can answer it and open enough that a teenager can pick their own topic. Ask the reverse next, since the worst thing is usually where the real news lives.
- 2
If you could pick dinner for the whole family tonight, what would you have me make?
Food is safe ground and the answer gives you something concrete to do together on the next visit. You also learn what they eat at home now, which changes faster than you would think.
- 3
What are you good at that most grown-ups have no idea about?
Kids are rarely asked to brag on their own terms, so this gets you the video game, the drawing style or the skateboard trick their report card never mentions. Ask for a demonstration.
- 4
What song have you had on repeat lately? Will you play it for me?
Asking to hear it, rather than just hear about it, turns the question into a shared five minutes. Your honest reaction matters less than the fact that you sat through the whole thing.
- 5
What is a word or phrase your friends use that I would get completely wrong?
It puts them in the expert seat and lets them laugh at you a little, which is worth a lot in an unequal relationship. It also gives you a running joke to reuse on the next call.
- 6
Who do you sit with at lunch, and what do you all talk about?
This gets at friendship without the loaded question of who your best friend is. Lunch seating tells you quickly whether they have a solid group or are drifting between tables.
- 7
What is something you made or built recently that you were proud of?
Pride in the making is different from pride in the grade, and this question rewards effort they chose themselves. Keep whatever they show you and mention it again months later.
- 8
If you could spend a whole day with any animal in the world, which one and what would you two do?
A pure imagination question for the younger ones, and a surprisingly revealing one for older kids who answer with something solitary or something loud. Nobody feels tested by it.
- 9
What do you think I was like when I was your age?
Their guess shows you the version of yourself they have assembled from photos and family stories. Correcting it gently is how a lot of family history gets handed over.
- 10
What is a subject or class you would take if nobody was grading it?
This separates genuine curiosity from performance and often points at an interest their parents have not noticed yet. It is a gift-buying answer and a career-conversation answer at once.
- 11
What is the hardest part about being your age right now?
It signals that you assume their life has real difficulty in it, which most adults do not say out loud to a child. Resist the urge to compare it to how hard things were for you.
- 12
What do you wish grown-ups would stop saying to you?
You will probably hear something you say yourself, and hearing it without arguing back is the whole point. This is the question that convinces a teenager you can be told the truth.
- 13
When you imagine yourself at twenty five, what does an ordinary Tuesday look like?
Asking about a Tuesday instead of a career gets you the life they actually want: the city, the roommate, the quiet morning. Vague ambitions turn specific when you ask about the day.
- 14
Is there a rule at home or at school that you think is genuinely unfair?
It teaches them that disagreement can be discussed rather than punished, and it shows you how they reason about authority. Stay curious even when you privately agree with the rule.
- 15
Who is someone you look up to that I have never met?
The answer might be a teacher, a coach, an older cousin or a stranger online, and each of those tells you something different about what they are reaching for. Ask what that person does that they admire.
- 16
What is something you tried that did not work out, and would you try it again?
Naming a failure out loud to someone who will not be disappointed is good practice for a kid. The second half of the question is where you find out whether the sting has faded.
- 17
Has anything been worrying you that you have not told anyone yet?
Grandparents are often the safest adult in the family because you are not the one enforcing bedtime or grades. Ask it quietly, side by side, and be ready to just listen and keep it.
- 18
What do you want to know about our family that nobody has told you?
This hands them the microphone on family history, and their questions are usually sharper than the stories you would have picked. It also surfaces gaps or rumors worth correcting.
- 19
What is your favorite thing we do together, and what do you wish we did more of?
The first half tells you which of your traditions has actually landed, and the second half is a direct request you can grant. Write down the answer and act on it within a month.
- 20
When you are my age, what do you hope you remember about me?
It asks them to imagine you as part of their long story, which changes the tone of everything that came before it. Expect a pause, and expect to be moved by whatever follows it.
How to Get Real Answers from a Grandchild
Practical guidance for the conversation itself.
Best Practices
Best Practices
Ask Side by Side, Not Face to Face
Eye contact raises the stakes for children and teenagers. The best answers come in the car, on a walk, while shelling peas, or during a puzzle. Give their hands something to do and their mouth loosens up.
Answer It Yourself First
Say your own answer in two or three sentences before you hand the question over. It models the length you are hoping for and proves the question is a trade rather than a test.
Count to Five Before You Speak Again
Most adults fill a three second silence with a follow-up or a hint. Let the pause stretch. Children very often start talking on second four, and that second answer is the honest one.
Use One Question, Not Twenty
This list is a menu, not a script. One good question per visit, followed by real curiosity, beats running the table and making the afternoon feel like paperwork.
What Shuts a Grandchild Down
What Shuts a Grandchild Down
Turning the Answer into Advice
If every disclosure comes back as a lesson, they stop disclosing. When you hear something worrying, respond with a question instead: how long has that been going on, or what do you want to happen next.
Comparing Them to Their Parent
Your son or daughter at that age is not a useful yardstick, and being told they are just like their mother lands as a verdict rather than a compliment. Let them be a first draft of themselves.
Asking with an Audience
A question that works one on one becomes a performance at the dinner table, especially for teenagers and especially in front of siblings. Save the searching questions for a private moment.
Reporting Back to Their Parents
If what they tell you reappears in a parent conversation, the channel closes for years. Keep it unless it involves safety, and if you must pass something on, tell them first.
Adjusting the Questions by Age
Adjusting the Questions by Age
Ages 4 to 7
- 1Make it concrete and about today: what made you laugh at school?
- 2Offer two choices rather than an open field: pancakes or noodles for our special dinner?
- 3Accept a drawing or an act-it-out as a complete answer.
Ages 8 to 12
- 1Lean on expertise: teach me how your game works.
- 2Ask about fairness, since this is the age it burns hottest.
- 3Invite show and tell: bring me the thing you made.
Teens and Adult Grandchildren
- 1Ask about their future in specifics, like an ordinary Tuesday at twenty five.
- 2Ask what you get wrong about their world, and take the answer without defending yourself.
- 3Trade something real of your own: a fear, a regret, a decision you are still unsure about.
Keeping What They Tell You
Keeping What They Tell You
- Keep a cheap notebook by your chair and write the date, the question and a line of their answer right after they leave.
- Ask permission before recording, then record audio rather than video, since a phone pointed at a child changes how they talk.
- Ask one repeating question every birthday, such as what is the hardest part about being your age, and keep the answers together.
- Read last year's answer back to them the following year and ask whether it still holds.
- For long distance, put one question in a text or a letter and let them answer whenever they want, which suits teenagers far better than a surprise phone call.
- Write down the follow-up they asked you for, like teaching them a recipe, and do it before the next visit.