10 Gambles Every Grandmother Should Take This Year to Improve Her Relationship with Her Grandkids

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As grandmothers, we cherish our role as nurturers, storytellers, and protectors. But if we want to deepen our bond with our grandkids, we sometimes have to take a leap of faith. Building a strong, meaningful relationship isn’t just about the traditions we’ve held onto for years—it’s also about embracing the new, stepping out of our comfort zone, and sometimes taking a few calculated risks.

This year, I encourage you to take a few gambles. Not the kind you find at a casino, but the kind that could pay off in laughter, trust, and unforgettable memories with your grandkids. Some of these might feel a little scary at first, but that’s the beauty of it. When we take a chance on love, we often find ourselves more connected, more joyful, and more alive.

So, let’s roll the dice and try these ten gambles that just might make this the best year yet for you and your grandkids.


1. Say Yes More Often

We grandmothers can be set in our ways. There’s a certain comfort in routine, in doing things the way we always have. But what if, this year, we said “yes” more often?

Your grandchild might invite you to try a virtual reality game, eat something that looks completely strange, or watch a show that seems ridiculous at first glance. Instead of brushing it off, why not go along with it? Saying yes to their world—even when it feels foreign—sends a powerful message: I care about what interests you. And who knows? You might even find yourself having fun in ways you never expected.


2. Share a Secret from Your Youth

To our grandkids, we can sometimes seem like we were always responsible, wise, and perfectly behaved. But we weren’t always grandmothers—we were once young, mischievous, and full of dreams.

Sharing a little secret from your youth—maybe a harmless prank you pulled, a time you took a risk, or a moment you broke the rules—can help your grandkids see you in a whole new light. It makes you relatable and reminds them that growing up is a journey full of lessons. And if your story comes with a lesson, all the better!


3. Let Them Teach You Something New

As grandmothers, we spend a lot of time teaching our grandkids—how to bake, how to sew, how to plant a garden, how to navigate life. But relationships are strongest when both sides feel valued. This year, gamble on letting them teach you something.

Maybe they want to show you how to use a new phone app, explain a trend you don’t understand, or teach you a skill they’ve mastered. Even if it doesn’t seem useful to you, give it a try! The simple act of letting them be the teacher gives them confidence, shows them you respect their knowledge, and strengthens your bond in ways you might not expect.


4. Plan a Surprise Just for Them

Grandkids love to be surprised—especially when it’s by someone they least expect. We often shower them with gifts on birthdays and holidays, but what about surprising them on an ordinary day?

Consider planning something unexpected—a handwritten letter sent through the mail, a spontaneous trip to their favorite ice cream shop, or a little treasure hunt at your house. The surprise doesn’t have to be big or expensive; what matters is that it makes them feel special and reminds them that you think about them even when you’re apart.


5. Admit When You’re Wrong

This might be one of the toughest gambles on the list. We grandmothers have a lifetime of wisdom, and sometimes it’s hard to admit when we’ve made a mistake. But if there’s one thing that builds trust with our grandkids, it’s humility.

If you lose your temper unfairly, misjudge a situation, or dismiss something important to them, be willing to say, “I was wrong, and I’m sorry.” It teaches them that learning and growing never stop, no matter how old we get. And it shows them that they, too, can admit mistakes without fear of losing respect.


6. Play a Prank on Them

Now, I’m not talking about anything mean-spirited—just some lighthearted fun. A harmless prank can create an inside joke that lasts for years.

Maybe you swap out their cereal for something unexpected, pretend you’ve forgotten how to use a common household item, or send them a silly message in a “grandma code” they have to decipher. Laughter is a wonderful way to bond, and showing your playful side will make your grandkids feel closer to you.


7. Let Them See You Be Silly

Speaking of laughter, when was the last time your grandkids saw you being truly silly? Not just smiling along with their antics, but really letting loose?

Sing at the top of your lungs, dance in the kitchen, or put on a funny voice during a story. Showing your playful side makes you more approachable and encourages your grandkids to be their authentic selves around you.


8. Give Them a Challenge

Kids love a good challenge, and they love beating their elders at something even more! This year, give your grandchild a playful challenge.

It could be a cooking contest, a puzzle race, or a storytelling competition where you both take turns adding to a tale. The key is to make it fun and let them have a chance to shine. Letting them win once in a while (or pretending to struggle just a bit) makes them feel capable and strong.


9. Try Something That Scares You

One of the best lessons we can pass on to our grandkids is the courage to step outside their comfort zone. And what better way to teach it than by example?

Maybe it’s trying a new food, learning how to use a new piece of technology, or even riding a bike again after years. When your grandkids see you trying something that challenges you, it sends the message that being brave isn’t about age—it’s about attitude.


10. Ask for Their Advice

We grandmothers are often seen as the ones who give advice, but asking for our grandkids’ opinions can be just as powerful.

Try asking them for guidance on something simple—what book to read next, what hairstyle to try, or what outfit looks best for a special event. When they see that you value their input, it strengthens their confidence and shows that respect goes both ways.


Taking the Gamble Is Worth It

Love isn’t just about playing it safe—it’s about taking chances, being vulnerable, and showing up in ways that surprise even us. Some of these gambles might feel a little uncomfortable at first, but the rewards? They’re immeasurable.

This year, let’s be the grandmothers who say yes, who laugh, who step into our grandkids’ world with an open heart. Because at the end of the day, the best memories aren’t made from staying in our comfort zones—they’re made from taking a chance on love.

So, which of these gambles are you willing to take this year? 💕

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