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  • Writer's pictureKelly

50 questions to ask your penpal and what not to ask.

Updated: Apr 16, 2020

When we first started with penpals, we were unsure what to ask. We didn’t want to ask questions that made people think what the actual heck, so we started making a list of questions that we considered suitable.

Growing up I always had a penpal, but in my teens I lost contact with them and I never found out why. Then when my kids started asking about finding pen pals I was hesitant. I didn’t want them to expect letters from others when they could end up with no reply. That is exactly what happened.

They found age suitable penpals exchanged a few letters and then nothing. So what do you ask a penpal? We have put together a list of what we think are great questions to ask your penpal. Hopefully you have better luck than we did!

Questions to ask your Pen Pal

Start with the obvious ones such as:

  1. What countries have you visited if any?

  2. Which celeb would you invite to dinner?

  3. What family members do you have?

  4. Have you ever made a time capsule?

  5. What did you put in the time capsule?

  6. What would you change about the world?

  7. What are you really good at?

  8. What are you bad at?

  9. Do you have a daily routine?

  10. What have you dressed up as for Halloween?

  11. Any unusual facts about yourself?

  12. What makes you happy?

  13. Do you do anything for work?

  14. What can you see right now?

  15. Do you collect anything?

  16. What are your goals for the month?

  17. Have you ever won anything?

  18. Do you have a nickname?

  19. Do you play any sports?

  20. Do you have any hobbies?

  21. What type of letter do like to recieve?

  22. What’s the most daring thing you’ve ever done?

  23. Hot or Cold?

  24. Dog or cat?

  25. Do you believe in God?

  26. Do you believe in ghosts?

  27. Do you believe in Aliens?

  28. Do you have own a car?

  29. How Tall are you ?

  30. When is your birthday ?

  31. What is the last movie you went to the cinema to see?

  32. Do you have a fashion style ?

  33. Tell me your life in 9 words?

  34. What shoes do you wear most of the time?

  35. What music do you like?

  36. Are you scared of anything?

  37. What was your school like?

  38. What is life like where you are from ?

  39. What would you wish for right now?

  40. What is the silliest thing you’ve ever done?

  41. Do you have any pets?


  1. What is your favourite colour?

  2. What is your favourite song?

  3. What is your favourite food?

  4. What is your favourite Movie?

  5. Who is your favourite superhero?

  6. Do you prefer a certain season?

  7. Do you have a favourite quote?

  8. Have you got a favourite book?

  9. What is your favourite animal?

My boys have a few really awesome penpals who they really need to get on with replying to them. They send things to each other like drawings and photos, coins and small items of no value. I love this, I love seeing how excited they get when they open a letter and see a drawing that someone has done for them.

What not to ask. The ultimate stay away sign!

The one thing that I have had in the past that really put me off was a letter from a guy who constantly went on about can you send me this? Can you send me that? All I want is to find a woman……… This really puts me off. I am just interested in being friends and sending mail. I have been ignored before when one found out I was married too! The boys have had a few people who never replied to them which made us think they just wanted freebies.

Hopefully you can gain some ideas from the questions above to get you started, once you discover things about each other it becomes a lot easier to keep the conversation flowing.

Hooperland X



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