Are You Always the One Reaching Out to Your Grandchildren?

You remember birthdays. You send messages. You ask about school, friends, and what’s new in the family.

You know your grandchildren love you. But sometimes you wonder: what would happen if you stopped being the first to reach out?

Would they call? Would they write? Would they know how to start a conversation?

I’m not a grandmother. I came to this question from the other side of the relationship. I’m a granddaughter.

My grandmother lived far away. I used to write her letters, sometimes slipping a photograph or a dried flower inside the envelope. My grandmother passed away four years ago. When we opened her dresser, we found all my letters carefully tucked away. She had displayed the photographs I sent her in places where she could see them every day.

I didn’t realize until then just how much those little letters had meant to her.

Years later, when I noticed how difficult it can be for children to write even simple letters, I created TaleMail, a project that introduces kids to real mail.

They may love their grandparents, relatives, and friends very much. But when an adult says, “Write Grandma a letter,” a child often has no idea where to begin.

And yet, imagine how much it means to a grandmother to receive something she can actually hold in her hands, something her grandchild touched, wrote, or drew.

Instead, try asking: “What happened today that Grandma might enjoy hearing about?”

Why It Can Be Hard for Children to Reach Out First

Making a phone call requires a young child to make several decisions at once: when to call, what to talk about, and how to keep a conversation going in real time.

Children also often get used to adults arranging family communication. Grandma sends a birthday card. Mom hands the child the phone to talk to Grandpa.

It may simply never occur to a child that they can be the one to reach out first.

For some kids, reaching out just doesn’t come naturally yet. A postcard can be a good first step. A child can take their time deciding whom to write to and what to say.

One sentence, a question, or even a drawing can be the beginning of a real exchange.

1. Ask Simpler Questions

When we ask broad questions, we often get very short answers.

Try asking about one specific moment:

• What toy did you play with today?
• Did you see anything today that you wish Grandma could have seen?
• Did anything surprise you at school?

An answer like “I saw a strange bug today” is perfectly fine.

Now the child already has the beginning of a letter:

“Grandma, today I saw a strange bug with a really big head! Have you ever seen a bug with a big head?”

2. Start a Family Mail Tradition

It’s easier for children to take the initiative when they understand how a familiar ritual works. For example, you could start a tradition called “Something Interesting That Happened This Week.”

Your grandchild chooses one thing to share, and Grandma writes back with a little story from her own life.

This is also the idea behind Mailo’s Grand Mail Kit, which I created to help children and grandparents exchange postcards. It includes simple writing prompts for children and reply cards for grandparents.

Gradually, the child begins noticing things throughout the day and thinking, “Oh, I should tell Grandma about that!”

Over time, thinking about Grandma becomes a natural part of everyday life.

The important thing is to keep the tradition simple and enjoyable.

If the child misses a week, don’t turn it into another unfinished assignment. Close relationships don’t require a perfect schedule.

3. Teach Your Grandchild How Mail Works

What is a stamp? Where do you write the address? What’s the difference between a letter and a postcard?

This is why I wrote What Is Mail?, a children’s book that introduces stamps, envelopes, postcards, and the journey of a letter in a way young children can understand.

Even these small things can be obstacles for a child. 

Grandparents can quietly help make the process easier. Send your grandchild a blank postcard with your address already written on it. If possible, include the postage, too.

At the top, write one simple prompt:

“Tell me what you had for breakfast today.”

For a younger child, leave some space for a drawing.

This doesn’t mean you’re doing the work for them. You’re simply helping them take that first step.

4. Start Small and Build from There

Children sometimes think they need something important or unusual to happen before they have anything worth writing about.

But closeness often grows through the ordinary little moments of everyday life.

A grandchild might write about a pancake that came out in a funny shape, a new leaf growing on a plant, or a joke a friend told at lunch.

For a grandmother, these stories offer a glimpse into the child’s daily life, the moments she doesn’t get to see herself.

Start with short messages. As children get used to sharing little moments, they may naturally begin adding more details to their stories.

5. Show Your Grandchild That Their Letters Really Matter

Show them that you keep their letters and read them again. Tell your grandchild that their letters have a special place in your home. Better yet, show them during a video call. Show them the photograph they sent you hanging on your refrigerator or standing in a frame.

When children see that you treasure their letters, they understand that their little stories really matter to you.

Staying Close Is a Skill Children Can Learn

If your grandchild rarely calls or writes first, it doesn’t necessarily mean they love you any less.

Sometimes children simply need a little help understanding that they, too, can play an active role in staying connected with the people they love.

Their first letter may contain just one sentence.

A postcard may have more drawings than words.

A phone call may last only three minutes.

But it’s a beginning.

It’s not about counting who calls or writes more often. What matters much more is helping a child one day think:

“I can think of Grandma. I can tell her something. I can be the one to write or call first.”

Maybe the next letter your grandchild sends will be the one you keep in your dresser for years.

What About Your Family?

Are you usually the one who calls or writes to your grandchildren first? What has helped your grandchildren begin reaching out to you on their own?