50 Conversation Starters + Happy Mail Inspo

Hello friends!

You know those posts where I share questions to ask your friend or pen pal or spouse? I’m back with a slightly shorter list today, as well as some pictures of a happy mail package I sent recently. Once again, credit for a lot of these questions goes to my fiancรฉ, Sully. I hope you enjoy answering them as much as I have!

Enjoy some thought-provoking questions and springy art. ๐Ÿ™‚

featured image 264

1. Do you have an active imagination, or a hard time “playing pretend”?

2. If you lived in the Stone Age, what would you miss most about the modern world? What would you enjoy most?

3. Which do you tolerate better: heat or cold?

4. What would be your least favorite job to have?

5. If you could go back in time and give advice to your younger self, what would you say?


6. What was a recent bad idea you had? A good one?

7. Do you like seafood? Favorite or least favorite kind?

8. Do you like sports? Favorite sport to play? To watch?

9. How do you pass the time on long drives? Do you play road games? Listen to music?

10. Would you rather have a small wedding or a big wedding?


11. What would you invent if you could?

12. How do you feel today?

13. Did you have sleepovers as a kid? Did you like them?

14. Least favorite literary trope?

15. What is a small thing or detail that you tend notice more than other people?


16. What did you eat for (breakfast, lunch, supper) today?

17. Would you ever want to go in a submarine or go scuba diving?

18. Which makes you more uncomfortable – heights (a.k.a. mountaintops) or depths (a.k.a. underwater)?

19. One of your spiritual strengths/weaknesses?

20. What’s your favorite movie quote?


21. Do you sleep in regular clothes or pajamas?

22. If you had your own radio station, what kind of songs would you play on it?

23. Who do you hope you’ll be by the end of your life?

24. What do you want your grandkids to call you? Grandpa, Grandma, etc.

25. What are you thankful for today?


26. Have you ever won a contest or giveaway?

27. What is your favorite kind of tree?

28. What is your opinion on diets?

29. Are you good at multitasking?

30. What are a few of your favorite words?


31. What’s your favorite kind of cereal?

32. What was the time you were most embarrassed?

33. How long do your showers usually take?

34. Do you usually pack a lot or a little when you travel?

35. Do you like public speaking?


36. If you could rid the world of one animal, which one would you choose?

37. If you could only eat one food group for a whole week, what would it be?

38. Are you a “save the best for last” person or not?

39. Which family member are you closest to?

40. Have you or your parents ever gotten a ticket?


41. What’s your favorite kind of dance?

42. Who’s your favorite fictional character?

43. What Biblical character can you most relate to/identify with?

44. Did you get an allowance growing up or have to earn money?

45. What passion of yours do you wish more people shared in the world?


{Both of these postcards are for sale on my Etsy shop here!}

46. What is one particular thing you’d love to have in your dream home?

47. What’s your favorite vacation you’ve been on?

48. Do you tend to be a more private person or a public person?

49. Are there any social causes you would stand up for in public?

50. Which of your parents do you take after more, in appearance or otherwise?


There we go! I hope you enjoyed that conversation-starter list and the happy mail inspiration scattered throughout.

I challenge you to pick one or more of these questions and answer it in the comments! ๐Ÿ™‚

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


P. S. If you liked this post, check out my other two “questions to ask” posts:

100 Questions to Ask Your Pen Pal

100 More Questions to Ask Your Pen Pal


28 thoughts on “50 Conversation Starters + Happy Mail Inspo

  1. Aww, cute! (I loved your hand-lettered postcard!) Thank you SO much for the creative list of questions! I know I need to ask more questions even in conversations, so this is suuper helpful!


  2. 40. Have you or your parents ever gotten a ticket?
    No. *knocks on wood* My dad did get a warning in a different country because the speed limit was different. I am not legally allowed to drive yet, and have never driven. ๐Ÿ˜ƒ
    And may I just say your artwork for the happy mail is gorgeous!!!๐Ÿ˜


    1. Ooh, good for them! My mom has, and my dad got a ticket but got out of it in court, hehe. I bet it would be extra stressful driving in a different country!
      Aww thank you. โค๏ธ


  3. Thanks for the interesting questions๐Ÿ™๐Ÿผ๐Ÿ’–. I’ll definitely be using these for my questions of the day. Also, I tolerate the cold better. I feel useless in the heat. I would rather have a big wedding. Not big, big but big. Speaking of weddings, it’s almost time for yours๐ŸŽ‰๐ŸŽ‰. How are things going?
    How do I feel today? Well, I feel good, it’s been a good day so yeah. How are you feeling?
    And yes, I’m very good at multitasking, are you?


    1. You’re most welcome! YES, I agree with you! I am always cold, but I think I’d rather be cold than too hot because I also feel useless in the heat. It makes me exhausted. Yes, I’m excited to have a big wedding too! We’re thinking it’s going to be about 250 people! Things are going great, thanks for asking. I want to send out the last few invitations today and help Sully move into our new house this week. I’m so glad you feel good today! What have you been up to? I feel good too. I just woke up but I feel well-rested. Yep, I’m pretty good at multitasking too. It’s a handy skill, right? ๐Ÿ˜›
      I loved hearing your answers, Sabrina!


      1. YESSS๐ŸŽ‰๐ŸŽ‰. When it’s cold there’s a lot you can do to warm up but when it’s hot there isn’t really much you can do to cool downโ€๐Ÿคทโ€โ™€๏ธ.
        250๐Ÿ˜ฏ?? I didn’t think that there would be that much people but then I’m sure that it will be amazing to have as many of your loved as possible there on your big day๐ŸŽ‰๐ŸŽ‰. Ohh sounds like things have been going well. Hope it stays that way๐ŸŽ‰๐ŸŽ‰.
        I recently hit 300 followers and I finally decided on a new name for my blog because I’m not a fan of the one I currently have. The younger me had no taste๐Ÿ˜‚๐Ÿ˜…. But yeah, the 300 followers one was a huge surprise because I just came back from a hiatus๐ŸŽ‰. Other than that, I haven’t been up to much except school ๐Ÿคธโ€โ™€๏ธ.
        A very handy skill indeed๐Ÿ˜›๐Ÿ˜‚.
        I enjoyed answering them too๐Ÿ’–.


        1. Exactly!
          Haha I know – we invited close to 400 but that’s how many we expect to attend. We’ll see! And thank you!
          Ah, congratulations on hitting 300 followers! That’s super exciting. โค HA, I feel you on old blog names. I've been wanting to change mine for a while yet. Yay, school… hehe. Well thanks for the update! I always enjoy hearing from you. ๐Ÿ™‚


            1. That’s what I’m praying too!
              Sounds like a plan! I think I’ll change my blog’s name to something like “Allison Marie” if I can find an available URL.


  4. This is awesome! I will definitely use some of these questions! And the artwork is lovely!
    I hope the wedding planning is going well. I know that wedding planning can be stressful (not saying out of experience; I just have a very large extended family and have been to many weddings and helped with many weddings) :). I will be praying that all the details come together quickly and easily!


    1. Woohoo! Glad you enjoyed, Ellie.
      It is definitely stressful at times but can also be quite fun. ๐Ÿ˜€ I finally got my invitations sent which is a relief, haha. Now I’m excited for some upcoming bridal showers! Thank you so so much for your prayers. It’s so neat that you’ve gotten to attend and help out with so many weddings!

      Liked by 1 person

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