52 Engaging Prompts for Grandparents Writing Letters to Grandchildren

As an Amazon Services LLC Associate, some of these items contain affiliate links, meaning if you click a link and make a purchase, we earn a small commission at no extra cost to you. Our recommendations are made to be genuinely helpful and useful.

I love opening up my mailbox and discovering what I like to call ‘real mail’! I love seeing the handwriting of someone I love. The fact that someone shared their time with me as they wrote brings joy to my heart. I can only imagine how my grandkids feel when they open their mailbox which is hours away from me and discover a letter from Amma. Suddenly the miles are non-existent. Writing letters to grandchildren is a heartfelt way to bridge the distance and maintain a close connection, no matter how far apart we are.

We’re taking a look at two of the oldest and easiest ways to correspond through mail, postcards and letters to grandchildren, and how they are a key component to bridging the distance with our grandkids.

Postcards

Postcards were developed as a quick and easy way to communicate, and that still holds true today! It’s true that the text that fits on a postcard could be similar to a text message. That message has so much meaning when received in the mail.

For this purpose, when you’re out and about, pick up a postcard, write a quick message and pop it in the mail. Even if it’s not a grand vacation!

• Send a postcard from your hometown. It will absolutely delight your grandchild because “this is where Amma and Papa live!”
• Share a fun kid’s joke with them.
• Create a short custom poem just for them – use their name in it if possible.
• If they love your pets, have fun sending a postcard ‘from’ your pet.
• Think about the things that they are interested in or involved in. Share a fun fact or recent stat about that subject.

Letters

Letters have been called a ‘lost art’ by many. Upon researching the history of letter writing, I discovered the great lengths people went to to write down important observations, traditions, and memories.

They used bricks of clay, stone, plant leaves, or bark long before paper was available. To write they used tools made from wood, metal, bone or reeds before the pens and pencils of today. Let’s not forget that those early ‘letters’ were then delivered by carriers with chariots and horses!

Well, that takes away any ‘reason’ I have for simply grabbing a piece of paper, jotting down some thoughts, putting it in an envelope, and walking it ‘all the way’ to my mailbox. Goodness, let’s get writing!

Remember! Some of our grandchildren are very busy. We may not always receive a response in the mail, but don’t let that stop you from using these prompts to send letters to grandchildren! And speaking of busy, check out these 26 Effective Tips for Communication with Busy Grandkids.

52 Ideas for Writing Letters to Grandchildren

Personal Experiences:

1. Describe a time when you struggled and how you persevered.
2. Share about a recent celebration.
3. Describe a funny or embarrassing moment from your past.
4. Write about a goal you set and how you achieved it.
5. Describe your first car and how you got it.
6. Write about a special talent you have.
7. Describe an adventure you had as a child.
8. Write about a time when you had to be brave.
9. Share a time when you helped someone in need.
10. Describe a time when you felt really proud of yourself.
11. Write about a time you overcame a fear.
12. Describe a memorable experience you had with nature.
13. Write about a time you had to apologize and how it felt.
14. Share your favorite way to relax and unwind.
15. Share a life lesson you’ve learned.
16. Describe a favorite season and what you love about it.
17. Write about your favorite holiday and how you celebrate it.
18. Describe your favorite place to visit and why.
19. Describe your dream vacation and what you would do.
20. Write about a historical event you lived through and its impact on you.
21. Write about a dream you had. Funny or serious!

Family and Relationships:

21. Describe your favorite childhood memory.
22. Share a story about your parents.
23. Write about the day their parent was born.
24. Share a funny family story.
25. Describe a favorite family vacation.
26. Describe a family tradition that you cherish.
27. Write about a special friendship and what made it unique.
28. Describe your favorite family recipe and how to make it.

Personal Beliefs and Values:

33. Share your thoughts on kindness and why it matters.
34. Share a piece of advice for making friends.
35. Share your thoughts on the importance of honesty.
36. Share a piece of advice you would give to your younger self.
37. Share a favorite quote and what it means to you.
38. Write about the value of hard work.
39. Share your thoughts on what makes a good friend.
40. Share your thoughts on the importance of staying positive.

Hobbies and Interests:

41. Write about your favorite book and why you love it.
42. Write about a favorite game or sport you played as a child.
43. Describe your ideal day and what you would do.
44. Share a recipe and why it’s special to you.
45. Describe a book you loved as a child and why.
46. Write about a hobby you enjoy and how you got started.
47. Write about your favorite movie and why you love it.
48. Describe a fun family game you used to play.
49. Write about your favorite type of music and why you love it.

Educational and Career Experiences:

49. Share about your education and what you studied.
50. Describe your first job and what you learned from it.
51. Write about a favorite teacher and the impact they had on you.

Interactive and Creative Prompts

52. Send an interactive fill-in-the-blank letter they can send back.

We are huge fans of providing simple ways to encourage grandkids responding through mail. Personally, I have seen huge success through utilizing mail to stay connected with my grandkids using the PLUS membership. I simply print out what I want to send each month and provide an extra copy for them to return. We love it!

The sending of mail is nothing new. Throughout history, mail has been delivered by horseback riders, stagecoach, steamboat, pony express, motorcycles, and planes, trains, and automobiles. It’s clear that mail was important! It seems every possible avenue of delivery was pursued. And that leads me to believe I need to pursue the act of writing letters to grandchildren with equal intentionality – it truly makes a difference in the lives of those sweet grandkids who are opening their mailboxes just hoping for a letter from you.