225 questions to ask your kids

....because better conversation leads to better relationships.

If there's one thing I’ve learned as a teacher, it’s this: conversation is the gateway to connection.

The more we talk with kids — like, really talk — the better we understand their world, their needs, their fears, and their dreams. But conversation doesn’t just happen…it needs a spark.

In this dance of dialogue, questions lead. They invite curiosity, build trust, and open doors to stories we might never hear otherwise.

I’ve always taken pride in being able to strike up a real conversation with any kid, whether they’re an open book or barely saying a word. Over the years, I’ve gathered a stash of go-to questions, which I’ve used for icebreakers, community building exercises, journal prompts, talking circles, restorative justice activities, goal-setting, casual conversation, and more.

In this post, I’m sharing 225 of my favorites (the first 50 are free), grouped into nine categories I use all the time in the classroom and beyond:

• Breaking the Ice

• Getting Acquainted

• Wellness Checks

• Exploring Values

• Community Building

• Taking Responsibility

• Curriculum Connections

• Hopes & Dreams

• Discussion & Debate

  

  “How was your day?” is boring and hard to answer. Try a “wellness check” question instead.

Just a quick note — these questions aren’t meant to be rattled off like an interview. Think of them as conversation starters, little sparks to help something meaningful unfold. Some will click right away, others might fall flat (and that’s totally normal). Use what feels right, skip what doesn’t, and let the dialogue flow naturally.

More than anything, I hope this list helps you feel a little more connected to the kids in your life, and gives you a few new ways to really hear them.

Icebreakers

Use these questions to start a talking circle or difficult conversation.

The purpose of "icebreaker" questions is to ease into open and honest conversation.

• If you could be an animal for a day, what would you be?

• If you had a time machine, where would you go?

• If you could only eat one food forever, what would it be?

• If your life had a theme song, what would it be?

• If you could have any superpower, what would it be?

• If you could meet any character from a book, who would it be?

• What is the worst haircut you've ever had?

• Would you rather it be permanently daytime or nighttime?

• If aliens came to earth & invited you to their planet, would you go?

• If you could travel anywhere in the world, where would you go?

• If your favorite color had a smell, what would it smell like?

• What do you think is the best job in the whole world?

• If you were a potato, how would you like to be cooked?

• What is your favorite month of the year?

• What is your favorite subject in school?

• What is the most unusual thing in your backpack right now?

• If you had to change your name, what would you change it to?

• What is your least favorite chore?

• What is your favorite game?

• What is your favorite show or Youtube channel?

• What is the worst injury you have ever had?

• If you had to be one age forever, what age would you be?

• How do you like your eggs cooked?

• Which emoji best describes you?

• Would you rather be too hot or too cold?

Getting Acquainted

Use these questions to introduce individuals or ideas.

"Getting acquainted" questions gently ease participants into deeper, more introspective topics.

• What are three words that friends would use to describe you?

• If you had one day to do anything, what would you do?

• What is something that makes your family special?

• If you could invent something to make life easier, what would it be?

• If you were mayor for a day, what would you do first?

• What is something that scares you?

• If your life was a movie, what would it be called?

• If you became famous, what would you be famous for?

• What is one of your happiest memories?

• What is something that makes you laugh?

• What is your favorite quality about yourself?

• If you could only take one item to a deserted island, what would it be?

• What is something that annoys you?

• If your life had a theme song, what would it be?

• Where do you feel most comfortable?

• If you found $100 right now, what would you do with it?

• What is the meaning of your name?

• Describe yourself using only one word.

• If you started a business, what would it be?

• What is your favorite holiday or tradition?

• Would you rather be able to pause or rewind your life?

• What is your favorite after-school activity?

• If you had an unlimited supply of only one item, what would it be?

• Are you a competitive person?

• Do you consider yourself to be normal?