80 Pen Pal Questions for Adults, From First Letter to Old Friends

The hardest part of having a pen pal isn't finding one. It's the blank page after "Dear...". These pen pal questions are written for adults and sorted by stage, so you always know what fits: easy ones for the first letter, everyday ones to keep it going, and deeper ones once you know each other.

The short answer: ask two to four open questions per letter, put them near the end, and build on what your pen pal told you last time. Start with everyday life and where they live, move to interests and memories, and save values and big questions for when you're friends.

Want a pen pal who replies today? Try a chat

New to pen pals? Start with what is a pen pal and how to get a pen pal.

How to ask pen pal questions well

• Answer before you ask. Reply to their letter first, then add your news, then your questions.
• Open, not yes/no. "What's your town like in winter?" beats "Is it cold there?"
• Follow up. "You said you started a new job. How's it going?" shows you read their letter. Follow-ups are better than any list.
• Share your own answer. If you ask about their favourite meal, tell them yours.
• Let skipped questions go. You can repeat one that seems forgotten, once. If they skip it again, they'd rather not say.

First letter questions (getting to know you)

Easy, friendly and safe to answer.

1. Where do you live, and what's it like there?
2. What does a normal day look like for you?
3. What do you do for work or study, and do you enjoy it?
4. What do you like doing when you have a free afternoon?
5. What made you want a pen pal?
6. What languages do you speak, or want to learn?
7. What's the weather doing where you are right now?
8. What three words would your friends use to describe you?
9. Do you have any pets?
10. What are you looking forward to this month?

Everyday life

Small questions get big answers in letters.

11. What did you have for breakfast today? 12. What's the view from your window?
12. How do you get to work or school?
13. What's a small thing that made you happy this week?
14. What's on your to-do list that you keep putting off?
15. What does your weekend usually look like?
16. What song have you been playing a lot lately?
17. What's the best thing you've bought for under ten dollars?
18. Are you a morning person or a night person?
19. What's something you do every day without fail?

Where you live and your culture

The best part of an international pen pal.

21. What's one thing tourists always get wrong about your country?
22. What's a dish from your home I should try, and how is it made?
23. Which holiday matters most to you, and how do you celebrate it?
24. What's a word in your language that has no good translation?
25. What do people in your town do on a Friday night?
26. What's a typical wedding or birthday like where you live?
27. Which place near you would you take a visitor first?
28. What's a common saying or proverb in your language?
29. What surprised you most about my country from what I've told you?
30. What's school like in your country, from what you remember?

Food, books, films and music

31. What's your comfort food?
32. What's the last book you couldn't put down?
33. Which film could you watch again and again?
34. What music did you grow up with at home?
35. What do you always order at your favourite café or restaurant?
36. Is there a book or film from your country you'd recommend to me?
37. What's a food you hated as a child but love now?
38. Which singer or band would you most like to see live?
39. What are you watching at the moment?
40. If you hosted a dinner, what would you cook?

Work, learning and plans

41. What did you want to be when you were little?
42. What's the best part of your job, and the worst?
43. What's something you're learning right now?
44. What skill would you like to have by next year?
45. What's the best advice anyone gave you about work?
46. If money didn't matter, how would you spend your days?
47. Where would you like to live one day?
48. What's on your travel list?

Memories and stories

49. What's your favourite memory from childhood?
50. What's the best trip you've ever taken?
51. What's the funniest thing that happened to you this year?
52. Who taught you the most when you were growing up?
53. What's a tradition from your family you want to keep?
54. What's the bravest thing you've done?
55. What was your town like when you were younger?
56. What's a moment you'd love to live again?

Fun questions and "would you rather"

Good for lighter letters, once you've settled in.

57. Would you rather live by the sea or in the mountains?
58. If you could have dinner with anyone, past or present, who would it be?
59. What animal best describes you, and why?
60. If you could instantly speak one more language, which would it be?
61. Would you rather visit the past or the future?
62. What would your perfect day off look like, hour by hour?
63. If you opened a small shop, what would it sell?
64. What's a strange talent you have?

For more like these, see our hypothetical questions.

Deeper questions (for when you're friends)

Wait until the letters feel easy and warm. Ask one at a time, and answer it yourself too.

65. What's something you believe that most people around you don't?
66. What has changed most about you in the last five years?
67. What does a good life look like to you?
68. What are you most proud of?
69. What's something hard you've been through that shaped you?
70. Who in your life do you most admire?
71. What do you worry about that you rarely tell anyone?
72. What do you think makes a good friend?
73. What would you tell your younger self?
74. What are you hoping for in the next year?

There are more in our questions to get to know someone deeply and philosophy questions.

Follow-up questions (the secret to long friendships)

Fill in the blanks from their last letter.

75. How did ___ go in the end?
76. You mentioned ___. Can you tell me more?
77. What happened next with ___?
78. Did you ever try ___ that you were talking about?
79. How are you feeling about ___ now?
80. What's changed since your last letter?

Pen pal letter ideas (besides questions)

A good letter gives as well as asks. Try adding:

• A "day in my life" told hour by hour.
• A photo or description of your street, your desk or your lunch.
• A recipe for something you cook often.
• A short playlist of songs you're listening to.
• A local word or phrase and what it means.
• A small story from your week, with a beginning, middle and end.
• Something you'd both do: read the same book or watch the same film, then write about it.

What not to ask (at least at first)

• Their home address, full name, workplace or phone number.
• Money, salary or anything about sending money.
• Looks, relationships or anything romantic.
• Politics and religion, unless they bring it up and you know each other well.

If someone pushes on these, it's fine to stop writing and block them. More in our safety tips for chatting with strangers.

Writing to someone in another language?

Keep questions short and clear, one idea per sentence, with no slang. That helps learners and translation tools alike. On Olu, a free, text-only chat for adults 18+, every message is translated both ways, so you can ask any of these questions to someone online now in another country, in your own language. It's instant chat rather than letters, and the community is small, so it's busiest at World hour, daily at 19:00 UTC (check yours with the time zone tool). Any AI partner is always labelled AI.

The short version

Answer first, ask two to four open questions, and follow up on what they told you. Start with everyday life, move to culture and stories, and save deep questions for later. And when you're stuck, describe something small and real. Those are the letters people remember.