For many, slowing down and spending quality time with our loved ones is often the best part of the holidays— even if that time is virtual this year. While adults may engage more easily, conversations with children often stall out after “yes” and “no.” Here are some open-ended questions to help get a meaningful conversation started!


• If you could be a part of any TV show/book – what show/book would it be?
• What is something you’re thankful for?
• If you had to give away your toys to someone, who would you give them to?
• What does a hug feel like?
• What do you think is in outer space?
• What’s your favorite shape?
• What are you really good at?
• Would you rather play in the rain or the snow?
• What is the weirdest thing you’ve ever eaten?
• Do you like when people share with you? Why?


• What are your friends talking about on the playground?
• What’s the best thing that happened to you today?
• What was the hardest part of your day?
• If you could make up a holiday, what would it be called?
• What word would you use to describe yourself?
• Would you rather sail the seas or climb a mountain?
• How many stars are in the galaxy?
• Can you describe a color without mentioning its name?
• If you could sit anywhere in class, where would that be?
• Tell me three times that you used your pencil today.

Middle School

• What’s one thing you really like about yourself? Why?
• What do you miss about being little?
• What have you heard about in the news? How did it make you feel?
• Would you rather work alone on school projects or in a group?
• What’s your favorite place to spend time?
• What do you worry about the most?
• If you could have one song play every time you entered a room, what would it be and why?
• Would you rather eat breakfast, lunch, or dinner for all of your meals?
• When was a time you laughed so hard that you cried?
• If you started your own business, what would your business do?

High School

• How did you help someone today?
• What’s the best part about growing up?
• What’s the coolest app I don’t have on my phone?
• What five words would you use to describe yourself?
• If you were President, what would you change first?
• Do you believe money can or can’t buy happiness?
• What’s something you’d stockpile if you found out it wasn’t going to be made anymore?
• What is your favorite book you’ve ever read?
• If you were going to bury a time capsule, what would you put in it?
• What is one thing you don’t know how to do yet, but wish you did?

And Beyond

• Which of your friends are you proudest of? Why?
• What’s the first thing you do when you get home for the day?
• If you were guaranteed to be good at something, what would you do?
• If someone gave you $50, what would you do with it?
• Which celebrity would play you in the movie of your life story?
• What personality trait has helped you the most?
• What have you waited in a really long line for?
• Who’s the last person you friended on social media?
• What’s the weirdest or best dream you had recently?
• Do you believe in love at first sight?

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