Discover why and how to write meaningful letters to your grandchildren. Get tips, prompts, and ideas for crafting heartfelt messages that bridge generations.

Do you have any letters from your grandparents? If you do, you know how special they are. There is no better way to stay connected than regularly writing letters to a grandchild! What’s more, letters are physical proof that you value your relationship with your grandchild. 

It’s not always easy to know what to write. It can be especially hard when your grandchild is too young to respond. You sometimes feel as if you are writing into a void! That’s why we’ve put together a year’s worth of prompts to help you get started. 

Each month has an overall theme and some questions to get you thinking about stories you can share with your grandchildren. To make things even easier, get our Grandparent Love Letters–you’ll have the perfect canvas for connecting month after month. 

The questions are just starting points, and some may not apply to your family. Feel free to go off on your own tangent after reading the prompts!

January: Share stories about winter

• What’s your favorite part about winter? Your least favorite?

• Did you live somewhere it snowed as a child? Did you ever get snowed in?

• What winter activities did you enjoy as a child?

• What did you do as a family during winter break?

• If you lived somewhere it didn’t snow, what were your winters like?

February: Share stories about Valentine’s Day.

• What was Valentine’s Day like when you were in school?

• Did you ever give a valentine to someone you had a secret crush on?

• Do you like celebrating it today?

• Do you like candy hearts or chocolates better and why?

• Did you make or buy valentines when you were young?

March: Share your favorite books and stories.

• If you could write a book, what would it be about?

• What was your favorite character as a child? What was your favorite book?

• What book did your grandchild’s parent love as a child?

• Do you like fiction or non-fiction better? Why?

• What story do you wish you could be part of?

April: Celebrate spring.

• What do you like about spring?

• Did you ever go on trips over spring break as a child?

• What makes you feel like it’s spring?

• Is there a season you like best and why?

• Do you have any rituals you follow in the spring, like cleaning the house or planting a garden?

May: All about animals

• What was your first pet? What sort of personality did it have?

• If you could have any kind of animal for a pet, what would it be?

• Have you ever seen any unusual wildlife?

• What’s your favorite animal? Share some trivia about it.

• If you could spend a day as any animal, what would it be and why?

June: Talk about travel.

• Where would you like to take your grandchild someday and why?

• Did you ever travel with your grandparents?

• What’s your favorite place you’ve ever visited?

• Would you travel to outer space if you had the chance?

• Have you ever traveled by boat, bus or train?

July: Share your hobbies.

• What hobbies do you enjoy? What do you enjoy about them?

• Is there anything you started doing as a child that you still enjoy doing today?

• What hobbies did your parents or grandparents share with you?

• Did your grandchild’s parents have any hobbies when they were kids?

• What’s a hobby you’d like to share with your grandchild and why?

August: Home is where you live.

• Would you rather live on a boat or in a treehouse?

• Why do you live where you do now?

• Where would you live if you could choose anywhere?

• What was your home like when you were your grandchild’s age?

• Did you ever live anywhere out of the ordinary?

September: Share your memories of school.

• What was your school like as a child?

• What did you like or dislike about school?

• What do you remember learning that has been useful in your life?

• What do you think is different about school now?

• Who was your favorite teacher and why?

October: Share memories of Halloween.

• What did you do for Halloween as a child?

• Do you remember any costumes you dressed up in?

• What did your neighborhood do?

• How is Halloween different today?

• What’s your favorite candy, and has that changed since you were young?

November: Share memories of news you have lived through.

• Where did you get your news when you were young?

• Do you remember any world events that impacted you?

• Did you know anyone famous?

• Were you or their parent ever in the newspaper?

• What’s happening in the world today that you think they will remember?

December: Holidays: share your holiday stories.

• What are your favorite holiday memories?

• What traditions did you enjoy as a child? As a parent?

• What was one of their parent’s favorite gifts or holiday foods?

• What holiday foods did your grandparents make?

Writing to children under five

Before your grandchild can read and write, your letters are not going to be very important to them. That doesn’t mean you shouldn’t write them, however! When they are older, they will have a written record of how often you thought of them, and they’ll treasure the stories you’ve shared. If your grandchild is very young, you may want to write these letters and collect them for when they are older. You could also send them and ask parents to keep them somewhere safe.

Writing to school age children

Once children are old enough to read and write and understand the passage of time, they will start to appreciate all the stories you share. As they get older, your letters can be an important way to get to know one another. You can begin to pose questions in your letters, asking them to call or write you with their answers. Don’t be discouraged if you don’t get responses, however. Keep writing and asking, so they know you are interested in their lives.

Writing to teenagers

Letters to teenagers can continue to ask questions, and you can begin to share more of your life’s wisdom. You can offer encouragement and share stories about struggles you had as a teen. They will love stories about their parents and aunts or uncles. Whatever you do, keep writing. Teens need to know that there are adults in their lives who will be there for them no matter what.

There are two parts to writing a letter to your grandchild.

One is the actual writing. Your letters don’t need to be long, or perfectly written. You can write on scrap paper. You can write on special stationery so the letter is clearly from you. You can use your vintage typewriter, or compose it on your laptop, then print and send it. You can use our Grandparent Love Letters templates.

In other words, you can do whatever feels easiest, most fun, or most meaningful to you! 

The second part is sometimes the hardest, and that’s actually doing it. Make it a part of your grandparenting routine! The best way for many of us is to block a regular hour on our calendar dedicated to writing. If your grandchild was born on the 7th of the month, put a reminder to write on the 7th of every month. Or set aside an hour on the first Saturday morning for letter writing. 

Like any habit, it will take practice and reminders before it becomes part of your routine. But it’s a habit that will pay off in a closer relationship to your grandchildren. And someday, you’ll open your mailbox and find a letter there for you!

Grandparent Love Letters are more than just mail.

Our Grandparent Love Letters templates help you share the stories and memories that make your family unique. These beautifully designed, printable templates will help you write a monthly letter that will foster connection.

Why should you write letters to your grandchildren?

Letters show you care: A monthly letter lets your grandchildren know you are thinking of them even when you aren’t together, and that you want to know more about their world.

Your stories matter: Letters are the perfect way to share your stories, and those stories are important. Children who know their family stories score higher on assessments of resiliency and mental health.

It’s an inexpensive, fun way to connect: A letter in the mail is the perfect way to delight your grandchildren without buying expensive toys or fancy gadgets. 

Want to get started? Get your Grandparent Love Letters now! Your PDF files will be delivered  upon purchase so you can send your first letter today!