50 Thought-Provoking Questions to Ask Your Teen

  1. Which would you rather have: $1 million today or 1 cent doubled every day for 30 days? (This teaches your teen about compound interest.) 
  2. Would you rather be the boss or employee, and what would make you better at one position versus the other? 
  3. If you could have only one superpower, what would it be? 
  4. Describe yourself in 5 words or less. 
  5. If you could give every person in the world a gift but it would have to be the same gift, what would that gift be? 
  6. Imagine you’re the President and you need to have 3 people to assist you. Who would you pick and why? 
  7. If you could set one rule for the family that we all have to follow, what would it be? 
  8. If you could live anywhere in the world, where would it be? 
  9. When do you feel a child or teen becomes an adult? 
  10. What have you learned in life that you feel will be the most useful? 
  11. Describe what a perfect day would be from the moment you wake up until bedtime. 
  12. If you could change anything in the world, what 3 things would it be and why? 
  13. If you could eat dinner with 3 people you don’t know, who would it be and where would you go? 
  14. Do you think it’s better to have one great skill you’re an A+ at or many skills you’re a C at and why? 
  15. What’s the best invention you’ve seen most recently and what do you like about it? 
  16. What makes our family amazing that you feel is unique about us? 
  17. What are 3 things you are grateful for in your life, and why? 
  18. What are 3 really small victories that you’ve had in the last few days that you’re proud of? 
  19. What’s a hobby that you don’t currently have that you’d love to learn? What’s holding you back? 
  20. What do you feel are the most important things to living a great life? 
  21. If we lost everything we owned today but could keep 3 things, what would you pick and why? 
  22. Imagine you’re the teacher tomorrow at school. What are 3 things you’d teach that you think would help make school more useful for one’s future? 
  23. When someone is feeling stressed, what are 3 suggestions you’d share with them on how to feel less stressed? 
  24. What do you feel is the hardest job in the world and why? 
  25. How would you explain the word “love” to someone without using the word “love?” 
  26. Do you believe money can or can’t buy happiness? 
  27. Think of the worst thing that’s happened to you…what did you learn from it? 
  28. Of all the things you’re learning, what do you think will be most useful as an adult? 
  29. If you could travel back in time 3 years, what advice would you give yourself? 
  30. Which of your friends do you think I would like most? Why? 
  31. If you could grow up to be famous, what would you be famous for? 
  32. How would you change the world if you could? 
  33. How can you help someone today? 
  34. If you could make one rule that everyone in the world had to follow, what would it be? 
  35. If you had enough money that you never had to work, what would you do with your time? 
  36. Have you passed up on any chances that you now regret? What were they? 
  37. If you were told you would live forever, what would you change about your life? 
  38. What are you most afraid of? 
  39. What do you think is keeping you from complete happiness? 
  40. What’s your greatest strength and your greatest weakness? 
  41. What is the achievement you’re most proud of and why? 
  42. What’s one thing you did in the last 24 hours to make someone’s life better? 
  43. Where in the world would you most like to live? 
  44. What’s had the greatest impact on your life, good or bad, and why? 
  45. What do you do when you can’t sleep at night? 
  46. If we experience our greatest moments of growth and learning from failure, why are we so afraid to fail? 
  47. What product would you stockpile if you found out it wasn’t going to be sold anymore? 
  48. Do you have any bad habits you wish you could break? What are they? 
  49. If you had no physical, financial or other obstacles, what skill would you like to have?