Endearist
DE EN Get Endearist

Question set · Kid

30 Fun What-If Questions to Ask Your Kid

30 playful what-if and would-you-rather questions to ask your kid — silly, imaginative scenarios that quietly reveal how their mind and their heart work.

By Endearist 30 questions

Ask a child what they did at school and you get three words. Ask them what they'd do with a pet dragon and you get a whole world. Hypotheticals slip past the shrug — they're a game, not an interview, and a kid will tell you who they are inside a made-up story long before they'd tell you straight out. These are the what-ifs and would-you-rathers that make a car ride fly and quietly show you how your child thinks.

Warm-up questions

  1. Would you rather be able to fly or be able to turn invisible? A perfect opener. Whichever they pick, ask what's the first thing they'd do with it.
  2. If you could have any animal in the world as a pet, what would it be? Follow with where it would sleep and what you'd feed it. The logistics are where the imagination really goes.
  3. Would you rather eat pizza every single day or ice cream every single day?
  4. If our house could be made of any food, which food would you pick? Ask which room would be which food. Silly architecture keeps the game rolling.
  5. Would you rather be as tall as a tree or as tiny as a mouse? The choice often hints at whether they crave being big and seen or small and sneaky. Just notice, don't analyze out loud.
  6. If you could swap places with any animal for one day, which would you be?
  7. Would you rather have a dragon that breathes fire or a unicorn that grants wishes? If they pick the wish-granter, sneak in: what's the first wish? You'll learn a lot.
  8. If you woke up tomorrow and could speak every language, who would you talk to first?
  9. Would you rather it rained chocolate or rained your favorite toys?
  10. If you had a robot that did one chore for you forever, which chore would it be? Their most-hated chore tells you something useful, dressed up as a game.

Going deeper

  1. If you could make one rule that everyone in the whole world had to follow, what would it be? Their rule shows what they think is unfair. Listen for the small injustice behind the big idea.
  2. If you found a magic button that could undo one mistake, would you use it? Stay light. If a real mistake surfaces, follow gently; if they keep it pretend, keep it pretend.
  3. Would you rather be the funniest kid in school or the smartest? What they reach for here often mirrors what they think gets them loved or noticed. Just take note.
  4. If you were in charge of our family for a whole day, what would change? A safe way to hear what your kid wishes were different at home. Take the answer seriously, even in a silly wrapper.
  5. If you could invent something brand new that nobody has ever made, what would it do?
  6. Would you rather always know when someone is lying, or always know what they're feeling? A surprisingly deep one in disguise. Whichever they choose, ask why that one matters more to them.
  7. If you got to design a brand new holiday, what would everyone do on it? What they want a whole day devoted to tells you what they treasure. Often it's just time with someone.
  8. If you could be any age you wanted, what age would you choose? Younger means they miss something; older means they're reaching for something. Ask what, gently.
  9. Would you rather go to space or go to the bottom of the ocean?
  10. If you could give one superpower to me, your parent, which one would you pick? Their answer often reveals what they wish you had more of — patience, time, a way to feel less tired.

The vulnerable ones

  1. If you could keep just one of your toys forever and the rest disappeared, which would you keep? The why behind the chosen one is usually a memory, not a feature. Ask for the story.
  2. If you could spend one whole day with anyone in the world, who would you choose? If they pick someone far away or no longer here, that's a window into who they miss. Stay soft.
  3. If you could give one wish to every kid in the world, what would you wish for them? Notice when the wish turns from candy to kindness. That shift is your kid's heart showing.
  4. If you could make one worry disappear forever, which worry would you pick? This is the gentlest way to learn what's quietly weighing on them. Don't fix it on the spot; just hear it.
  5. If you could be remembered for being really good at one thing, what would you want it to be?
  6. If you could send a message to yourself when you're all grown up, what would it say? Write down what they say word for word. Your future self and theirs will both treasure it.
  7. If you could make grown-ups understand one thing about being a kid, what would it be? This question quietly invites a real complaint in safe clothes. Receive it without getting defensive.
  8. If you could keep one feeling forever and never lose it, which feeling would you keep?
  9. If our family had a magic spell that always worked, what should the spell do? What they want the family magic to do is often what they most want for the people they love. Listen closely.
  10. If you could keep one memory forever, even when you're very, very old, which one would you choose? A lovely place to end. Whatever they name, tell them you'll remember it too. Then actually do.

What to do with the answers

The most honest answer you'll get tonight is gone in three months unless you write it down. Endearist keeps it — per person, end-to-end encrypted, with a cadence reminder so you can pick the thread back up next time without scrolling through your messages.

More questions for your kid

More questions about hypotheticals

Related tools

Frequently asked

What age are these questions best for?

Roughly five to twelve, with the warm-ups landing for the youngest and the deeper ones for kids around eight and up. You know your child best — if a question is too big, swap it for a sillier one and circle back in a year. The whole list is built to be playful first, so there's never any harm in skipping ahead or starting over.

My kid just says 'I don't know' to everything. What now?

Answer first yourself, with a genuinely silly choice. Kids mirror — once they see you'd live in a house made of waffles, the floodgates open. You can also offer two funny options and let them pick, which is easier than inventing from a blank page. And don't push; some days a child just wants quiet, and forcing the game is the fastest way to kill it.

When is the best time to ask these?

Side by side beats face to face for kids — in the car, on a walk, at bath time, doing a puzzle. Children open up most when there's no eye contact pinning them down and the question feels like part of the play, not a sit-down talk. Bedtime is gold for the gentler ones. Mealtimes work too, as long as it stays a game and not a round of questioning.

A silly question made my kid say something serious or sad. Should I have avoided it?

Not at all — that's the quiet gift of hypotheticals. They give a child a safe, pretend doorway to say a real thing they couldn't say head-on. When it turns tender, just follow their lead: slow down, listen, don't rush to fix or to cheer them back up. If they want to return to silly afterward, let them. You learned something they trusted you with.

How do I remember the funny and tender answers before I forget them?

Jot them down the same evening, while the exact words are fresh — the wording is half the charm and it fades fast. Endearist gives each child their own private, end-to-end encrypted page where these little gems can live, so years from now you can read back the day they wanted a house made of waffles. These are the lines you'll wish you'd kept, and almost nobody does.