100 More Questions to Ask Your Pen Pal

Hello, my friends!

If you love writing letters but don’t know what to talk about, this post is for you! Even if you don’t have a pen pal, you can use these questions as conversation starters with your friends or family. Questions are just fun, and a great way to get to know someone better. If these aren’t enough, check out my first pen pal questions post here.

Okay, enjoy this huge variety of questions with some happy mail inspiration along the way!

  1. If you had to live in another country, which one would you choose?

2. How much sleep do you usually get? Do you feel like you get more or less than you should?

3. Does your family have any traditions?

4. If you were an animal, what animal would you be? What is your “spirit animal”?

5. What website or app do you spend the most time on? 

6. Do you like car rides? Can you drive/are you learning to drive/do you like driving?

7. Have you ever been unconscious before?

8. Favorite flower?

9. Do you like listening to music while studying or doing other things? If so, what kind?

10. Do you know what your reading or typing speed is?

instagram 518

11. What is your favorite ethnic cuisine? (Mexican, Italian, Chinese, etc.)

12. What superpower would you choose and why? 

13. Favorite artist? Art style? Art period? Painting? Sculpture?

14. What is your least and least favorite day of the week?

15. Are you a saver or a spender?

16. Do you like to sing, hum, or whistle?

17. Do you prefer to plan things out and know what’s coming, or be spontaneous and let yourself be surprised?

18. What kind of humor is funniest to you? (Satire, puns, slapstick humor, etc.)

19. What’s your favorite virtue to find in other people? How about your least favorite vice?

20. Do you like water? The ocean? Swimming pools? Water parks? Rainy days? Mud puddles?

instagram 522

21. Do you know what your “love language” is?

22. If you could only listen to music from one decade the rest of your life, what years would you pick? (80s, 90s, etc.)

23. What would you do today if you knew tomorrow was your last day on earth?

24. Are you organized or messy?

25. What is something you like and something you dislike about yourself?

26. Do you tend to make meals from scratch, buy already prepared meals, or go out to eat?

27. What is your opinion on inside pets?

28. What is your favorite Disney prince or princess?

29. What’s an experience you’ve had or period of your life that helped you mature or grow?

30. Do you have any special mementos or objects you keep for sentimental reasons? If so, what’s the story behind them?

instagram 645

31. What does your name mean?

32. How many children would you want if you had a family?

33. When is your birthday?

34. What is your favorite scent?

35. Baths or showers?

36. Do you gravitate toward consistency and routine or adventure and change?

37. Are you mostly right-brained or left-brained? (Creative or logical.)

38. If you could choose (or go back and choose), would you go to public school, private school, or be homeschooled? Where would/do you want to go to college?

39. What’s the worst thing ever? Best thing ever?

40. What was your worst injury?

instagram 722

41. What is your testimony?

42. What was your first dream job? What is it now?

43. How do you fit or not fit into your gender stereotype? (For instance, if you’re a girl – are there any tomboyish things about you?)

44. Are you good at acting? Do you like it?

45. Favorite bird? 

46. What is your favorite and least favorite part about being _____? (An adult, a teenager, the oldest, the youngest, etc.)

47. If you could freeze your life so you were a certain age forever (only including years you’ve already lived), which would you choose?

48. What was the best day of your life? The worst day?

49. Would you rather lose your sight or your hearing?

50. What’s the most well-written book you’ve ever read?

instagram 723

51. What’s the longest you’ve been without sleep?

52. Do you snore, sleepwalk, or talk in your sleep?

53. Are you a procrastinator?

54. What is your opinion on adoption? Would you ever adopt?

55. A few of the most important traits you’d look for in a person you’d want to marry (or already did)?

56. Do you ever reward yourself for accomplishing something? If so, how?

57. What’s your dream car?

58. Are you more of a leader or a follower?

59. Any foods or restaurants you cannot abide?

60. Do you dip cookies in milk? Graham crackers? Oreos?

instagram 744

61. What’s a weird food combination you enjoy?

62. If you had three wishes, what would you wish for? (You can’t wish for more wishes!)

63. Do you have perfect vision? If not, do you wear contacts or glasses?

64. Are you protective?

65. Do you like fixing things? How about making things?

66. Are you ticklish?

67. What are your parents’ names?

68. What ethnicity are you or were you ancestors?

69. What do you call your grandparents?

70. If you knew you wouldn’t die/get sick/get injured for one day, what would you do?

instagram 748

71. How often do you go to the dentist? Brush your teeth? Floss?

72. Do you like tattoos? Would you get one?

73. Have you ever dyed your hair? What color would you dye it?

74. Do you usually make birthday/Christmas lists, or let people surprise you?

75. Do you like driving/riding with the windows down? Do you like opening the windows in your house?

76. When you listen to music, do you sing along?

77. Who is your favorite villain/antagonist?

78. Seedless watermelon or regular?

79. What is something that helps you fall asleep?

80. Do you believe in soulmates? 

instagram 675

81. Do you think you act differently in writing vs. in person? If so, how?

82. Do you like mushrooms? Spinach? Broccoli? Peas? Coconut?

83. What do you keep in your purse/bag/wallet/backpack?

84. Are you good at memorization?

85. Which one would you choose: power, fame, or fortune?

86. Where is your favorite place to shop?

87. When you read a book, how clearly can you picture the characters, places, or what is happening?

88. Do you think or remember in words, pictures, sounds, or emotions?

89. How was your day? What did you do?

90. What is your favorite meal, snack, or food to make?

instagram 676

91. How often do you get sick?

92. What is your favorite kind of chair or seat to sit on?

93. Do you usually remember your dreams? What was the best or worst dream you ever had? Any recurring dreams?

94. Would you take a bullet for anyone? If so, who?

95. Do you share a room? Would you change that if you could?

96. What is your favorite thing to drink?

97. What is a bad habit you have? A good one? 

98. Do you tend to initiate conversations or wait until someone else does?

99. Have you ever moved? If so, when and where?

100. What is something you wish more people knew about you?


And that’s it, guys! Here are a couple of graphics if you’d like to pin your favorite list(s) for future reference, or print it out to check off as you go. 🙂

100 More Pen Pal Questions part 1
100 More Pen Pal Questions part 2
100 More Pen Pal Questions part 3
100 More Pen Pal Questions part 4

I hope you guys enjoyed that list and the happy mail inspiration mixed in. 🙂 (If you want an easy way to take your happy mail to the next level, check out the decorated envelopes here on my Etsy shop!) 

I challenge you to pick a number from 1-100 and answer that question in the comments. 😀

Thanks so much for reading, my friends, and have a lovely day!



55 thoughts on “100 More Questions to Ask Your Pen Pal

  1. Great list Allison! Here is maybe a couple of questions I can ask my husband to whom I’ve been married to for 25 years 😉.
    I’ll answer nr 51 – what is the longest you’ve been without sleep: Must be close to 34 hours 👀👀 … it was just as Covid-19 broke out in the world last year March. We’ve been in Egypt for a diving holiday and had to get back to South Africa as quick as possible. After hours of struggling to get flights back to South Africa, we’ve spent endless hours on different airports and in planes until we’ve eventually we’ve got home about 34 hours later. Maybe I did close my eyes for a quick nap during the times on the different planes … but then, when we got home, we almost slept for 24 hours continuously 😄.

    Liked by 1 person

    1. Thank you! Hehe, I love that. Hope you two have fun. 🙂
      34 hours without sleep… good grief. That sounds MISERABLE. Man, what a rough few days! Thank you so much for sharing that story, though – I really enjoyed reading it even though it doesn’t sound fun to live through. I bet that 24 hours of sleep felt blissful. 🙂

      Liked by 1 person

  2. Awesome questions Alison😁. I include a “question of the day” at the end of every post and I’ve kinda been struggling to come up with some😛. These are a great help❤. And they could start a whole conversation 😁.
    I’m gonna answer number 58. I’m more of a leader
    And as for number 76, I always end up singing along😅. I’ll always be like I’m not gonna sing I’m just gonna listen and I’ll find myself singing😂😅.
    Once again awesome post❤

    Liked by 1 person

    1. Thank you so much! Well YAY, I’m so glad it’s helpful for you! Yeah, a lot of them are great conversation starters!
      Good for you. I admire leaders but I’m more of a follower. And ha, I sing along a lot too! It’s just hard not to sometimes… YEAH, I feel you. I’m so glad you enjoyed the post, Sabrina! I enjoyed your comment too. 🙂


  3. Ohh, great post!! I love reading questions to ask your pen pal posts because I have like my second official pen pal and I am constantly needing new questions to ask! XD

    #36 Do you gravitate toward consistency and routine or adventure and change? Ummm, consistency and routine! I do like adventure and change, it just depends on what it is….. well, adventure at least. I hate change! XD

    Have a wonderful day!!!!

    Liked by 1 person

    1. YAY, I’m glad this could come in handy for you! I know, I run out of questions when I don’t have a list too. XD
      Yeahhhh, I feel you. That’s pretty much how I am too. Adventure is fun, but it depends. I usually gravitate toward consistency because it makes me feel safe. And change is almost always upsetting but also exciting if it’s a good change!

      Liked by 1 person

    1. Ooh yeah, good answer. I’d rather lose my hearing because I’m more of a visual learner, but I would DEFINITELY miss music. I’m grateful I have both vision and hearing, haha! And that’s a great idea to use these questions as journaling prompts!

      Liked by 1 person

  4. So cute! And much needed, absolutely gonna use these! Also the art OH MY GOODNESS GIRL!! So much talent I absolutely love it all!
    I picked a random number and it was 72. Do you like tattoos? Would you get one? Yes and yes! I already have so many planned out 🙂
    Also any tips on getting a pen pal?? I Have a few friends I do it with here where I live but I would love to have an international or just across the states one 🙂


    1. Well wonderful! I’m so glad to hear it. And AGH THANK YOUUUU.
      Hehe, what is one of the designs you have planned?
      Most of my pen pals are blogger friends I’ve known for a while! But you can also do friends or family you don’t see often that live far away. That’s fun too!

      Liked by 1 person

      1. Well…it has so many farm supplies and farm-y things. they have animal supplies and farm toys and even more stuff! It’s a very cool place!!!


  5. You’re welcome!!
    And I have a few I want to get for my family! My dad always tells me he loves me in sign language so I’m going to get the I love you sign tattooed on my wrist 🙂 My brother and I are also getting matching glow in the dark tattoos!
    Those are really good ideas! Thank you 🙂


  6. This is my first time on this page (or any page) in a while. Your stationery and handwriting as well as your tips are incredible. Keep posting this kind of stuff! It gives me ideas for my pen pals 🙂


  7. I really needed this, haha, lately I’ve been having a hard time finding interesting and unique questions for letters so this is literally perfect! 😀 Thank you so much! ❤


  8. Perfect timing for this post, Allison! I’ve been running out of questions for my pen pal’s mail tag, besides the “what’s your favorite…” questions. I’ll also use some of these as I complete my 52 letter writing challenge. I’m almost there! Here’s a few answers:

    9. If you hear strings and piano music, it’s probably me studying or reading while listening my favorite genre: Classical music. 🙂

    24. I always try to stay organized, but messes always happen, especially when I’m crafting. ‘

    95. Yup, I share a room with my 8-year old sister, and although we’re 10 years apart, I wouldn’t change a thing! In fact, my older sister who is now moved out used to be in our room too. The best memories are made by sharing a room. 🙂


    1. Wonderful! Whoa, the 52 letter writing challenge sounds so neat! Is it one a week?
      Ooh, classical music is lovely to listen to as backcground music.
      Ha, I feel you with messy crafting.
      Aww, that’s so sweet. ❤ I know, I love the memories from sharing a room! I share a room with my sister and have practically since she was born.
      Thanks for the lovely comment! I loved hearing your answers.


      1. Yup, the 52 letter writing challenge is one a week! I’m actually posting pictures every week over on my blog to hold myself accountable. I’ve gotten behind on blogging (thanks to a new full time job), but I’m hoping to catch up on posting soon! I only missed one week and I got ahead in the beginning, so I’m at 32 letters so far. It has been really fun to get replies back from people I’m not expecting to write back. 🙂


        1. Whoa, that’s neat! Actually I think I follow or follow someone who was doing that challenge on Instagram. My goodness, 32 so far?! Wow! That does sound really fun.


  9. 1. If you had to live in another country which one would you choose?
    It’s my dream to go to Europe, I think I would choose France😍
    Thank you so so much for this! Always can use more questions!!! I honestly don’t know how you came up with 100 more! That’s amazing😄
    And your envelope art, BEAUTIFUL.
    You have inspired me so much, Thank you!!!


    1. Yesss France sounds so beautiful. ❤ Would you go to the city, like Paris, or the country?
      I'm so glad you enjoyed! Haha well I didn't come up with all of them – I asked if I could use some from my friends and siblings. 😉
      THANK YOU! I'm so happy to hear I've inspired you, dear!


  10. Oh this is sooooo helpful! Thank you so much! I definitely find myself running out of questions to ask my long-term pen pals haha! (also your envelopes are just AMAZING)


Your comments make my day! Please keep them clean and respectful so everyone can enjoy this blog. :) Thank you!

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s