Halloween questions to ask your family: hands of different ages reaching into a carved pumpkin filled with folded paper slips on a candlelit table

Want your Halloween gathering to be about more than who got the most sweets? The best Halloween conversation starters for families are playful, a little spooky and easy for every age to answer, like "If you could be any monster for one night, which would you pick?" or "What's the spookiest story anyone in our family tells?"

There's something fitting about it, too. Long before costumes and chocolate, the old Celtic festival of Samhain, which Halloween grew out of, was a night for gathering round a fire and telling stories as the dark half of the year began. A good question simply brings that back.

Below are 40 questions, sorted so you can pick the right ones for your crowd, plus a simple pumpkin bowl game for Halloween night, which falls on Saturday 31 October this year.

40 questions, five kinds of Halloween night

Eight in each group. Mix and match for your crowd.

  • 1 to 8Little onesSpooky, but silly rather than scary.
  • 9 to 16Costumes and treatsEasy openers for any age.
  • 17 to 24Would you ratherQuick picks with big debates.
  • 25 to 32Family storiesFor grandparents, aunties and uncles.
  • 33 to 40Teens and grown-upsA little deeper, still fun.

Spooky but silly questions for young children

Little ones love Halloween when it's more giggly than scary. These questions let them be in charge of the monsters.

  1. If you had a friendly monster as a pet, what would it look like and what would you name it?
  2. What does a ghost do on its day off?
  3. If our house were haunted, what would the ghost be called?
  4. Which is scarier: a spider the size of a cat, or a cat the size of a bus?
  5. If you were a witch or a wizard, what would your first spell do?
  6. What would a vampire eat for breakfast if it didn't like blood?
  7. What would a pumpkin say if it could talk after being carved?
  8. Which friendly monster would make the best babysitter?

Costume and treat questions for everyone

These are the easy openers. Everyone at the table has an answer, from the four year old to the grandparent who insists they're too old for costumes.

  1. If you could wear any costume at all, with no budget and no rules, what would you be?
  2. What's the best costume you've ever worn, and who made it?
  3. Which sweet or treat would you trade everything else for?
  4. Which treat is the most disappointing to get in your bag?
  5. If our family did a group costume, what theme should we choose?
  6. Who in this family would make the most convincing vampire?
  7. What's the best Halloween snack you've ever made or eaten?
  8. If you could design a brand new Halloween sweet, what would it taste like?
A glowing carved pumpkin and a basket of sweets on a veranda step at dusk.
Costume and treat questions are the easy way in. Everyone has an answer, whatever their age.

Halloween would you rather questions

Read one out, everyone picks, then everyone has to explain. The explaining is where the fun is.

  1. Would you rather spend a night in a haunted house, or a night in a graveyard?
  2. Would you rather be a vampire who can't have garlic, or a werewolf who can't have chocolate?
  3. Would you rather have a ghost that tidies your room, or one that does your homework?
  4. Would you rather be able to turn invisible, or walk through walls?
  5. Would you rather trick or treat in the rain, or in a costume that itches all night?
  6. Would you rather carve a pumpkin with your eyes closed, or eat a whole raw pumpkin slice?
  7. Would you rather live in a castle with bats, or a cottage with a black cat that talks?
  8. Would you rather get only fruit when you trick or treat, or only toothbrushes?

If your family enjoys this round, there's a whole list of would you rather questions on our site, and plenty of them work round a family table too.

Questions that bring out family ghost stories

This is where the grown-ups get a turn. Aim these at grandparents, aunties and uncles, and give them time. In many Caribbean families, someone still remembers a duppy story told on a dark veranda, and those are exactly the stories worth hearing again.

  1. What did Halloween, or the nights around it, look like when you were a child?
  2. What's the spookiest story anyone ever told you when you were young?
  3. Did anyone in the family tell duppy stories or ghost tales? Can you remember one?
  4. Was there a house, a tree or a road near where you grew up that everyone said was haunted?
  5. What were you most afraid of as a child, and when did you stop being scared of it?
  6. What's the strangest thing that has ever happened to you that you still can't explain?
  7. Which relative always had the best stories, and what did they sound like telling them?
  8. Is there a family superstition we still follow without knowing why?

These are the answers children remember for years. If your family enjoys them, keep going on another night with our 50 questions for family dinners, which has a whole set for family stories.

Empty chairs with blankets drawn close around a glowing garden fire pit at night.
Ghost stories were told round fires long before Halloween had costumes. Give the storytellers time.

Halloween questions for teens and grown-ups

Older kids often go quiet at family gatherings, but many of them light up when they're asked for a real opinion. Answer honestly yourself, and don't turn it into a lesson.

  1. Which horror film cliché annoys you the most?
  2. In a zombie story, would you be the planner, the fighter or the one who hides? Be honest.
  3. Who in this family would be first to go and investigate a strange noise downstairs?
  4. What's something that genuinely scares you that other people find silly?
  5. Do you enjoy being scared, or do you avoid it? Why do you think that is?
  6. What's a scary film, book or game you think the rest of us should try?
  7. If you could ask one ghost from history a question, who and what would you ask?
  8. What's a fear you've faced this year that you're quietly proud of?

How to play the pumpkin bowl question game

You don't need a board, cards or an app for this. You need a bowl, some paper and about five minutes to set it up before everyone arrives.

The pumpkin bowl game

A small ritual that works at the table, by a fire pit or between trick or treat rounds.

  1. Before the nightWrite the slipsTen to fifteen questions from this page, one per slip.
  2. Fill the bowlFold and dropA bowl or a hollowed-out pumpkin, if you've carved one.
  3. Take turnsDraw and readThe youngest reader goes first. Everyone answers.
  4. AlwaysPass is allowedNo one has to answer. They'll join in on the next one.

A few twists keep it lively:

  • Answer apart, then reveal. For the would you rather questions, everyone writes their pick on a scrap of paper first, then you all turn them over at once. No copying the person next to you.
  • Guess the answer. Before Grandma answers, everyone guesses what she'll say. Points for the closest guess, if your family likes keeping score.
  • Torch rule. Turn the lights down and pass a torch. Only the person holding it can talk, which is especially good for the ghost story questions.

Three slips to get the bowl started

Fold them up, drop them in, and add your own.

  • What does a ghost do on its day off?
  • What's the spookiest story you heard as a child?
  • Who here would investigate a strange noise first?
Let the children write some slips themselves. Their questions are usually the best ones of the night.

Making it work on the night

Halloween gatherings are busy, noisy and full of sugar, so keep expectations light. One or two good conversations are a win.

  • Start the questions while people are eating or waiting, not when everyone is heading out of the door.
  • Pick questions for the youngest person present first, so nobody feels left out.
  • If a question lands flat, laugh and draw another. There's no wrong way to play.
  • When a story takes off, let it run and forget the bowl for a while. That's the whole point.
  • Jot down a favourite answer or two afterwards. Next Halloween you can read them back.

For relatives who live far away, the same questions work on a video call. Send each household three questions in advance, and let them answer in costume. And if the grown-ups want to keep talking once the children are in bed, our questions to ask your best friend work just as well between siblings and cousins.

If your family would like a question on ordinary days too, Our Little Thing has a Family option with its own questions: you each answer in private, passing one phone across the table or pairing two, then reveal your answers together. Our free question of the day is a simple way to try the idea first.

Questions about Halloween family conversation

What are good Halloween conversation starters for a family?

Questions that are playful, a little spooky and easy for every age, like which costume you'd wear if you could be anything, or which family member would survive a haunted house. Mix in a few that ask grown-ups for a story, such as their best Halloween or the spookiest tale they heard as a child.

How do you play a Halloween question game at a party?

Write questions on slips of paper and put them in a bowl or a hollowed-out pumpkin. Take turns drawing one, read it out and let everyone answer, with passing always allowed. It works at the table, round a fire pit or between rounds of trick or treating.

What are some spooky questions to ask family that won't scare young children?

Keep them silly rather than frightening: which friendly monster would make the best babysitter, what a ghost would do on its day off, or what a haunted house in your street would be called. Save the ghost stories for older children and grown-ups.

What are fun Halloween questions for game night with teens?

Teens usually enjoy would you rather questions and ones that ask their opinion, like which horror film cliché annoys them most or who in the family would be first to investigate a strange noise. Let them read the questions out, and answer honestly yourself.

How many questions do you need for a Halloween gathering?

Ten to fifteen is plenty for an evening, and even three or four will get a table talking. Stop while everyone is still laughing, and keep the rest for next year.