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20 Pillow Talk Questions for You and Your Child

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Before you tell your children good night, ask them a Pillow Talk question. I started doing Pillow Talks with my children when they were very young.

These conversation starters are a great way to connect with your child at a heart level, instead of at the “do this, do that” level where we engage with our children during most of the day.

And, if you’d rather connect before bedtime, here are 15 more ways to use these conversation starters. Here are 20 engaging pillow talk questions for you and your child.

  1. What do you like to dream about?
  2. What is your best memory this school year?
  3. Who is your hero? Why?
  4. How would you describe your family?
  5. If you could change anything about yourself, what would it be?
  6. What are you most proud of yourself for?
  7. Who is the kindest person you know? Why?
  8. What do you like most about your best friend?
  9. What is one thing you would like to learn to do well?
  10. If you were an animal, what one would you be and why?
  11. When is the last time someone hurt your feelings? How did you react?
  12. Do you know someone who is going through a hard time? How can you help them?
  13. What is the scariest thing that happened this year?
  14. If you could keep only one thing, out of everything you have, what would it be?
  15. Who do you think is really successful? Why?
  16. What’s the best thing about your teacher this year?
  17. When do you feel misunderstood by grown-ups?
  18. What three words best describe you?
  19. What’s something that makes you angry?
  20. What’s the best compliment you ever received?

What’s your favorite question above and why?


What is your favorite time of the day and why?

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