100 Original Random Questions to Ask a Teenager

This post contains affiliate links. If you click and buy we may make a commission, at no additional charge to you. Please see our disclosure policy for more details.

Sharing is Caring!

Coaxing teens into starting a conversation with you is not often an easy feat! Depending on whether or not they like what you’re asking them, they may avoid you entirely.

But, fostering your relationship through conversation is vital at this time. Your teen is growing into their own person, and it’s worthwhile getting to know who that is!

Try out some of these fun, original random questions to take them by surprise!

Best Random Questions to Ask Teens

The Best Random Questions to Ask Teens

  1. What is your favorite flavor of soda?
  2. If you could only eat at one takeaway restaurant for the rest of your life, which would you choose?
  3. If you saved 10 cents every week for twenty years, how much money would you save?
  4. How old do you want to be when you have your first child if you want to have any?
  5. Do you think that cigarettes and alcohol should be legal?
  6. Where would you book tickets to if you could go anywhere in the world right now for free?
  7. Which would you choose – a beach holiday or a winter getaway?
  8. What exotic cuisine do you like the most?
  9. What vegetable is your least favorite to eat and why?
  10. How many of your friends share the same religion with you?
  11. What is your favorite candy?
  12. If you could paint your room any color, which color would you choose?
  13. Ice cream cake or sponge cake – which would you prefer for your next birthday?
  14. What would your ultimate vacation look like?
  15. Which theme park would you want to visit one day and why?
  16. Would you rather be rich or famous?
  17. How many kids do you want to have in the future?
  18. In your opinion, who is the coolest celebrity, and why?
  19. Which university or college do you want to go to after you graduate and why?
  20. What hobby would you like to take up in your spare time?
  21. What does the perfect gift look like to you?
  22. What activities do you like to do with your friends?
  23. Which is your oldest friend, and how long have you been friends?
  24. What is your favorite ice cream flavor?
  25. Which is your ultimate takeaway meal and why?
  26. Tell me your funniest joke?
  27. What is your favorite family meal?
  28. What is your best memory?
  29. Which board game is your favorite to play with friends and family?
  30. Which is your favorite relax spot around town?
  31. Who is your favorite teacher?
  32. What is your theory of why the chicken actually did cross the road?
  33. Where do you think is the best place to grab a coffee or tea in town?
  34. How do you think the universe came to be?
  35. Do you think there is a purpose to life? If so, what?
  36. What do you think about marriage?
  37. Who’s your favorite – your dad/mom or me?
  38. Who’s your favorite sibling?
  39. What’s the scariest dream you’ve ever had?
  40. What’s the best dream you’ve ever had?
  41. What’s the most embarrassing thing that’s ever happened to you?
  42. What is your favorite animal?
  43. Which weird animal would you be willing to take on as a pet?
  44. Would you ever swim with sharks?
  45. Would you bungee jump for $1000?
  46. How would you get your hair styled if you could do it any way you liked?
  47. What is your favorite outfit to wear out?
  48. What is your favorite band or song currently?
  49. Would you ever learn a musical instrument? If so, what?
  50. Would you ever learn another language for fun? If so, what?
  51. What is your least favorite school subject?
  52. Would you ever drink pickle juice?
  53. What do you think about eating animals, eggs, and dairy?
  54. What is your proudest achievement?
  55. How do you handle feelings of jealousy, rage, anger, and hurt?
  56. Who would you have dinner with if you could choose anyone, including people from history and celebrities? Why?
  57. What genre of music is your favorite at the moment?
  58. What would you be willing to die for?
  59. Where would you like to travel to in the future?
  60. Where would you like to live when you’re older?
  61. Which three things can’t you live without?
  62. Which is worse – Brussell sprouts or broccoli?
  63. Which holiday is your favorite – Christmas, Easter, Halloween, or another occasion?
  64. Are you a cat person or a dog person?
  65. What is your favorite joke?
  66. What is your dream career?
  67. Where do you see yourself in twenty years?
  68. What food would you eat for the rest of your life if you could only choose one thing?
  69. What would you do if you won the lottery?
  70. Do you want to be wealthy when you’re older?
  71. What’s the best thing in your life right now?
  72. What are you saving up to buy at present?
  73. Do you prefer sweet treats to savory snacks?
  74. What is the most dangerous thing you’ve ever done?
  75. Which board game is your favorite to play with friends and family?
  76. If you could travel back in time to any moment in your life, which would you choose?
  77. How many pets do you want to have when you live on your own?
  78. Would you rather adopt a child or have your own?
  79. Would you rather adopt a cat or dog or buy a puppy or kitten?
  80. What does the perfect partner look like to you?
  81. What personality traits are most important to you in a partner?
  82. Do you think that everyone should be free to dress however they want?
  83. What clothes do you think will be fashionable in your kid’s time?
  84. What hairstyles do you think kids of the future will be wearing?
  85. How would you dress if you had no budget?
  86. Do you think that kids and teens should get pocket money? If so, why?
  87. What card games do you know how to play?
  88. What are your three favorite things about yourself?
  89. What is your favorite flavor of chips?
  90. What is the name of your favorite restaurant?
  91. What do you want to do for your next birthday?
  92. What does your ultimate birthday party look like?
  93. Would you choose never to age if you had the chance?
  94. What superpower would you love to have and why?
  95. What do you think happens after we die?
  96. Are you religious or spiritual?
  97. Are there any special skills you want to learn this year?
  98. What hobbies do you want to take up if you could do anything?
  99. Do you like to spend time alone or prefer to spend time with friends?
  100. Do you consider yourself an introvert or an extrovert?


Fostering a relationship with teens can be challenging but very worthwhile! Hopefully, these random questions spark a meaningful conversation with them.

Sharing is Caring!

Leave a Comment