100 Fantastic Questions To Ask Your Penpal

Has your mind gone blank? Have you hit a snail mail wall? It can be difficult to think of new questions and subject to chat about, especially with a new pal.. You could even try making a mail tag with a few questions.

I hope my list of 100 questions to ask your penpal will help you out.. I have used this on my own penpals in the past with great success..





  1. If you were granted three wishes what would you wish for?
  2. What is your favourite flower?
  3. What is your favourite cocktail and how do you make it?
  4. If you could relive any day of your life which would you choose and why?
  5. When did you last cry and why?
  6. What song can you always listen to that will instantly make you happy?
  7. What did your/do your parents do for a living?
  8. What career did you want when you were a child?
  9. What was your first pet and what was it called?
  10. What is your favourite boardgames and do you usually win?
  11. Have you ever broken the law? What happened?
  12. What animal would you like to be reincarnated into?
  13. If you had one super power what would you choose?
  14. If you were invisible for one day what would you do?
  15. What is the first thing you do when you wake up in the morning?
  16. What one possession can you not live without?
  17. What is in your handbag right now?
  18. What was your first cellphone?
  19. What film have you watched more than 10 times?
  20. Your favourite childhood book?
  21. Describe yourself in 3 words…
  22. What is your favourite way to exercise?
  23. What is your favourite milkshake?
  24. Do you have any bad habits?
  25. What is your favourite way to relax?
  26. Describe your perfect Sunday…
  27. What was your best vacation, where did you go and who with?
  28. If you could only eat one food for the rest of your life what would you choose?
  29. If someone locked you in a room for 24 hours and you could only hear one song over and over what would it be?
  30. Can you dance?
  31. Have you ever met anyone famous?
  32. If you could have a meal with anyone alive, dead, famous, not famous who would it be?
  33. What is your favourite season?
  34. What is your favourite mode of transport?
  35. Would you rather spend a day off exploring or sleeping?
  36. What time do you usually wake up in the morning?
  37. Are you an early bird or a night owl?
  38. What is your favourite TV show?
  39. What one TV show could you binge watch over and over?
  40. If you were a Sex and the city character who would you be?
  41. Dirty Dancing or Grease?
  42. Who was your childhood famous crush?
  43. What childhood toy would you still play with today?
  44. What is your favourite video game?
  45. Mario or Sonic?
  46. Tell me a fact about you that not many people know?
  47. Who was your first love?
  48. Did you have a teddybear when you were a child and what was its name?
  49. Barbie or Sindy?
  50. What is your favourite snack at the cinema?
  51. Can you swim?
  52. Do you have any tattoos?
  53. Do you have any piercings?
  54. Do you have a tattoo or a piercing that you regret?
  55. What is your least favourite feature about yourself?
  56. Are you closer to your mother or father?
  57. Do you have any siblings?
  58. Do you have any pets?
  59. Do you have a top 5 travel bucket list?
  60. How do you take your coffee?
  61. Do yo follow any sports religiously?
  62. What one food do you really hate?
  63. Is there a smell that you really hate?
  64. Have you ever sent a text message that you regretted?
  65. What is the worst hangover you ever had?
  66. What was your most embarrassing moment?
  67. Cats or dogs?
  68. Have you ever been on a motorbike?
  69. Have you ever ridden a horse?
  70. What is your most hated household chore?
  71. What is your favourite household chore?
  72. If you could change one thing about your past what would it be?
  73. If someone was to play you in a film about your life who would it be?
  74. If you only had 24 hours to live what would you do?
  75. If the world was going to end where would you go and what would you do?
  76. What is your favourite website?
  77. Where is your favourite place to buy stationary?
  78. What is your favourite App?
  79. Are there any games you are currently addicted to?
  80. Do you read any magazines?
  81. Who is your favourite actor and actress?
  82. Who is your favourite singer?
  83. Have you ever had any fashion disasters?
  84. Have you ever been in a fight?
  85. Have you ever broken a bone?
  86. Have you ever had an operation?
  87. Where do you seen yourself in 10 years?
  88. Would you like to be famous?
  89. What is the biggest bargain you ever found?
  90. What was your first car?
  91. What would be your ideal car if money was no option?
  92. If you won the lottery what 3 top things would you do?
  93. Would you ever go on a world cruise?
  94. Do you support a football team?
  95. Have you ever been bitten by an animal?
  96. Are you scared of anything?
  97. What is your favourite colour?
  98. What are you three favourite pastimes?
  99. What word do you overuse?
  100. Who is your best friend?

That should certainly keep you and your penpal busy for a while 🙂 I would love to add to this list so if you can think of any more questions please add them in the comments below and I can add them to the list…

Happy snailmailing x