100 Questions to Ask Your Pen Pal

Hello, dears!

I’m super excited for this post! (How unusual. πŸ˜› ) One of my readers recently requested I write about pen pal questions, so here we are. Asking/answering questions in letters (or in life!) helps you connect with and get to know someone better, plus, pro tip: including questions is one secret to making your letters a lot longer and more interesting. πŸ˜‰ For some of my pen pals, we insert a list of questions in the letter, and for others, we just ask questions as they come up about whatever subject we’re on.

Today I’m going to give you a ginormous list of 100 questions to ask your pen pal – some serious, some funny, all across a variety of topics and categories. If you’re at a loss for what to write, try some of these! I’ll also stick in a little happy mail/envelope art inspo along the way. πŸ˜‰ Alright, let’s do this!

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1. If you had to talk for fifteen minutes about something, what would it be?
2. What is something you wish you could change about the world?
3. Favorite ice cream flavor?
4. What was the last thing that made you laugh?
5. What colors do you wear, mainly?
6. Do you prefer writing things down digitally or on paper?
7. What are a few things that remind you of your childhood?
8. What is your favorite and least favorite part of ____ (whatever season you’re in)?
9. What stresses you out?
10. Are you more of a girly-girl or a tomboy?

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11. What is your middle name?
12. What are your favorite girl or boy names?
13. What does your morning/evening routine look like?
14. What’s something you’re oddly passionate about?
15. Do you have any hidden talents?
16. Which freaks you out the most: mice/rats, bugs, spiders, or snakes?
17. What is your greatest fear?
18. What is your favorite color scheme?
19. How do you spend your free time?
20. What are a few of your favorite Bible verses or quotes?

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21. What are your thoughts on social media?
22. Do you like wearing makeup?
23. What makes you really sad?
24. What are some things that make you really happy?
25. What do you daydream about?
26. Are you an introvert or an extrovert?
27. What do you believe about ____? (God, relationships, current issues, etc.)
28. What are your thoughts on personality typing?
29. What does eating healthy mean to you?
30. What would be the tastiest meal, in your opinion?

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31. Have you broken any bones or gotten stitches?
32. How tall are you?
33. What was one of the scariest moments/days of your life?
34. Do you like wearing jewelry?
35. What was the highlight of your day?
36. If you could travel anywhere for free, where would you go?
37. What kind of car or truck do you want to get?
38. What would your dream house look like?
39. What “aesthetic” do you love?
40. What style of decor do you love? (i.e. farmhouse, modern, vintage, etc.)

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41. Are you a hugger?
42. Do you like music? How do you usually enjoy it? (i. e. singing, listening, playing)
43. Do you play any instruments?
44. How many siblings do you have?
45. Do you have a big or small extended family?
46. Does your family have any inside jokes?
47. What is one thing you’re excited for and one thing you’re afraid of in the future?
48. What are a few of your favorite movies?
49. Does your family have any ____ traditions? (i. e. summer, Christmas, weekend, etc.)
50. What are some of your favorite memories?

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51. What are a few of your favorite books?
52. Do you prefer real books, e-books, or audiobooks?
53. What is something you’re struggling with right now?
54. What is something you’re super excited about right now?
55. Do you like nicknames? Do you have any?
56. Coffee, tea, or hot chocolate?
57. Beach or mountains?
58. One unpopular opinion you have?
59. What do your vacations usually look like?
60. How do you say ____? (i. e. “pecan,” “soda/pop/soft drink/etc.” “supper vs. dinner”)

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61. Where have you traveled?
62. How would your friends describe you?
63. What do you think people’s first impression of you is?
64. How do you want to be remembered?
65. What are a few words that describe you?
66. Do you write your letters over a long period or all at once?
67. Do you prefer writing with pencils or pens?
68. What is your favorite craft/art supply?
69. What are a few of your favorite songs or artists right now?
70. Math or science?

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71. What is your favorite thing to do with friends?
72. What is your love language?
73. What is your favorite and least favorite chore?
74. What are a couple of your pet peeves?
75. Where do you usually write letters?
76. What is your favorite animal?
77. What are your hobbies or interests? (i. e. reading, horseback riding, architecture, art, etc.)
78. Do you have any pets?
79. Do you put water on your toothbrush before or after the toothpaste?
80. Do you like pineapple on pizza?

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81. What does your week normally look like?
82. Do you live in the city, country, or somewhere in between?
83. What are a few things you’re grateful for right now?
84. What do you imagine your life will look like in ten years?
85. Who are your role models?
86. If you could meet with any person, past or present, who would it be?
87. What is your favorite and least favorite thing about your appearance?
88. What is your favorite and least favorite part of your character/personality?
89. What would a perfect day look like to you?
90. What is your favorite flower?

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91. Do you have a favorite number?
92. Do you imagine shapes, numbers, days of the week to have colors or personalities?
93. What color is your hair? Your eyes?
94. What is the view out the nearest window?
95. If you could take any class you wanted, what would it be on?
96. What makes you cry?
97. What makes you laugh?
98. What is your favorite snack?
99. When do you usually get up, and go to bed?
100. How can I pray for you?


Need even more questions? Check out my second post here:

Otherwise, 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. πŸ™‚

Pinterest Questions 1
Pinterest Questions 2
Pinterest Questions 3
Pinterest Questions 4

I hope you guys enjoyed that list and the happy mail inspiration mixed in. πŸ™‚ (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.) This post was honestly so much fun to put together! Would you like to see more like it in the future?

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

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


P. S. Photos taken with my Nikon D3400 and a 35mm lens.


74 thoughts on “100 Questions to Ask Your Pen Pal

  1. What a wonderful idea! πŸ˜€ Since I wrote letters a LOT, this is VERY useful!! Also, the pictures were extremely pretty. 😍😍


    Liked by 1 person

    1. She is doing amazing, thanks for asking! She’s much stronger and while she still has to rest a lot of the day, she is able to be with us for meal times and go outside and such. Praise God. ❀

      Liked by 1 person

  2. Wow! That’s a lot of questions! I will definitely be using some of these first chance I get! For now, though, I’ll take you up on the challenge and answer questions 1 and 16.

    1. I could totally talk about history or my latest writing project for fifteen minutes.(But I’ll stop here before I actually do that. XD)

    16. Right now, spiders freak me out the most, but only because I found one crawling on my dress this morning. I’m not usually freaked out very easily, though. I well remember the days when I would catch garter snakes with my brothers just because we thought it was fun. πŸ˜€

    Liked by 2 people

    1. It IS! Ha ha. And ooh, thanks for answering the questions!
      1. Heh heh, good for you. I am not wonderful at history, although I just watched Hamilton on Disney+ with my friends and loved it. Does that count? XD
      2. EW. GROSS. Haha, that’s great. Yeah, I like spiders from a distance because they’re fascinating, but I wouldn’t want them (or snakes) to actually crawl on me. :[]


  3. Amazing questions and photos. For the question 1 challenge, here’s my answer: I’ll tell my school friend all the fun and exciting things happened to me during the lockdown. Actually, I’ll be able to talk for more than 15 minutes. I can literally make a post on it! Yesterday, I and my friend texted about all this and we had a whopping 600 texts exchanged between us in a day! Sorry if I talked a lot about myself. This post is totally awesome.

    Liked by 1 person

    1. Thanks so much! WOW, that’s great, ha ha! I love getting updates from my friends like that. (But we often do long emails instead of texts.) Oh no, I love getting to know you guys better!

      Liked by 1 person

  4. Your post rocked. Still, I’ll like to suggest that it would be fun if more gossip y questions are added to your list. You know, the kinda stuff we talk with a BFF. Coz after you know your pen pal better, you can confide them in your secrets,incidents etc.😊 Other than this TINY detail, I liked your post a lot!!!


    1. Thanks! Ha ha, well I try not to gossip in my letters because that can be hurtful to others, but I know what you mean – it IS nice to be able to “confide” in your pen pals. πŸ™‚ I’m glad you liked the post!

      Liked by 1 person

  5. Great questions!! I’m answering two just because :).
    Some of my favorite books? *puzzles out how to narrow them down*
    The Lord of the Rings, The Silmarillion, The Hobbit, Someone Named Eva, And Then There Were None, The Mysterious Benedict Society (the whole series, I should say), and Ella Enchanted. And a thousand others, hehe.
    Audiobooks sometimes frustrate me because I have the characters’ voices in my head when reading for myself and when other people read them it doesn’t sound the same as I had imagined. E-books are all right, but after a while they can give you a headache from just staring at a a screen for several hours. Also, the downside of both of those is you aren’t actually holding a physical copy of the book. I prefer having the actual book there with me, just because I think you get a better feel for the story and can lose yourself in it more than with an audiobook or e-book.

    Liked by 1 person

    1. YAY ANSWERS! That makes me happy.
      51. Excellent choices! I’ve read LOTR, The Hobbit, MBS, and Ella Enchanted, which are all great books. I’ll admit I am not brave enough to read The Silmarillion (XD), but now I want to check out the other two I haven’t read!
      52. Oooohhh good point. And YES. I definitely prefer a physical book! Although I do find audiobooks helpful for, like, non-fiction books that don’t have a lot of characters. Otherwise I don’t care for them because I can read at a much faster speed than the person talks, which is annoying. πŸ˜›


  6. I love this idea. I love the questions about what you believe and how you would decorate a home. Those say a lot about a person. I would love to begin letter writing, but I don’t really know anyone who would want to receive a letter.

    Liked by 1 person

    1. Thank you so much! And I know, right? They really do. Aww, that’s too bad. :/ Do you have any friends out of state? Often you can ask blogger friends you know as well! Sadly I already have as many pen pals as I can keep up with, but I hope you can find one!

      Liked by 1 person

  7. GREAT ideas! I recently gained a pen pal, and I’m having so much fun writing and receiving letters! But I will admit, that sometimes my well of questions to asks seems to run dry. But this post has come to the rescue!! Thank you, Allison! πŸ™‚

    A note about “And Then There Were None”, by Agatha Christie… I saw this book recommended in another comment. While Agatha Christie shows what a genius she is in that book, it is extremely creepy and not for someone who lets themselves get fully immersed in books. Especially this one, because you as the reader are allowed to be inside each character’s heads in turn. And oh boy… that just takes the already immense creepiness to the next level. I… I was sickened, terrified, and had a super hard time sleeping that night. At the age of 17, for the first time in many years, had the urge to flee to my parents room.

    So. If you can handle scary books that get psychological and… well… as the title suggests, everyone dies, then go ahead and read this book! I definitely appreciated the genius of it, even though I could barely handle the creeps. But this book is NOT for the faint of heart, even if they consider themselves pretty brave people (i.e., I consider myself pretty brave when it comes to books and movies but I couldn’t handle this one).

    I read the book for the first time this past Sunday in basically one sitting and now I’m suddenly seeing people mention this book everywhere. It’s the weirdest thing.

    Anyway, sorry for the long comment and semi-rant. I just had to warn you before you picked up ATTWN. *shudders*

    Liked by 1 person

    1. Well yay! I’m so glad this post was helpful to you!
      Wooooow. That sounds like quite the book. O.o Thanks for the warning, Kendra! I have read a couple of Agatha Christie’s books in the past and they were fine, but that is definitely good to know. :[]

      Liked by 1 person

      1. I have read Agatha Christie books previously too, and I really enjoyed them (especially Murder on the Orient Express), but this one completely took me by surprise. In retrospect, after it’s been a few days, I might read it again at some point because it really was a very thrilling mystery with a lot o genius behind it. I think I’ll just wait a few years. XD

        Liked by 1 person

  8. Thanks so much for doing this post! I was so excited when I saw this in my Reader! Me and one of my pen pals are starting to write longer letters (it feels more like a conversation now and we are getting to know each other a lot more), so I am making a list of questions to ask her for future letters. I am definitely going to add some of these to my list!

    Liked by 1 person

  9. Yayyyy!! I’ve been hoping you would do a question’s list post!! So, huzzah! πŸ˜€ These are all wonderful! I’m gonna go print them out right now! πŸ™‚

    -Laura ❀ πŸ™‚

    Liked by 1 person

  10. I recently got a lot of pen pals and LOVE writing letters! This post was amazing! Sometimes I run out of things to ask so thank you so much for restocking my supply of questions! Now I will answer Two of the questions #44 I have 8 siblings. #75 I usually write letters at my desk. Oh, and one last thing I just wanted to let you know that I am praying for your mom and glad to hear that she is getting better!

    Liked by 1 person

    1. That is SO fun, Eliana! Yay! I’m so glad this post was helpful, and I loved hearing your answers! Also thank you so, so much for your prayers. ❀


  11. This is an awesome post! I have a lot of pen pals and sometimes run out of questions to ask, so I’ll definitely be bookmarking this to come back to later! I chose the random number 36 – if I could travel anywhere free, I would love to go to Copenhagen πŸ™‚

    Liked by 1 person

  12. #99: I usually go to bed by 9:30 but there are times I end up going later. IN the morning I get up at 5:30 to start the day which includes feeding my two cats. These are great questions.


      1. It is an early Morning. Thank you. Yes I have two cats a brother and sister name Sky and Tiger. I got them at Christmas time in 2014. They have been my source of comfort.


  13. Allison, thank you SO Much For this!!! 🌻❀️It’s been so helpful because I write a lot of letters!
    I appreciate you and your posts and the pictures of the letter and extras were also very inspiring!
    I am in my teens, and a friend and I started pen palling about last year and I’ve become obsessed with it and now I have several penpals, actually not several, A LOT. πŸ˜‚ but that friend and I have stuck with it the longest and go ALL OUT with our letters, it really is a fun old fashion thing to do!😍🌻
    Thank you!


    1. YAYYYY, I’m so happy this was helpful, Alana! That means a lot. Haha good for you. I agree, having pen pals is such a fun “old-fashioned” thing to do, as is going all out with your letters. πŸ˜‰ Thanks for this comment! It made me smile.


  14. Allison, fine job here; I don’t have Pen Pals per-say but if I ever do this is my road map to doing it perfectly! What an elaborate fine-tuned explanation of the ins and outs or how to get her done!
    I’m finding that with you it’s a matter of β€œdoing the job right” and that is very commendable! Good for you!
    My hat is off to you once again; and yes the hat we were just talking about the other day! πŸ˜‰ πŸ‘


  15. This was a very helpful post. It really inspired me giving me some interesting things to ask my pen pals. Thank you!

    10. I am definitely leaning towards being a tomboy.
    52. Real books are my go-to for sure!


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