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As grandmothers, we know that one of the greatest joys in life is hearing about the hearts and lives of our grandchildren. Whether they are tiny toddlers or grown adults, staying connected to them means we must create an environment where they feel safe, loved, and genuinely listened to.
But if we’re being honest, sometimes it’s not easy to get past the usual one-word answers like “fine,” “good,” or “nothing much.” That’s why we need to sprinkle in leading phrases—little open doors that make it easier for our grandchildren to step through and share more about their real thoughts and feelings.
Today, I’m sharing 35 gentle, heart-opening phrases you can use to encourage deeper conversations with your grandchildren, whether you’re sitting across the kitchen table or chatting on the phone.
Why Leading Phrases Matter
When we use a leading phrase instead of a yes-or-no question, we aren’t just asking for facts—we’re inviting a story. We’re telling our grandchild, “Your life matters to me. I want to understand, not just hear.”
This invitation to share helps build trust, strengthens emotional bonds, and even helps grandchildren process their experiences in healthy ways. And when they realize Grandma is truly interested in their world, they’re far more likely to keep coming back to talk again and again.
Now, let’s dive into those 35 golden conversation starters:
35 Leading Phrases to Help Your Grandchildren Open Up
1. “Tell me about the best part of your day.”
This invites a story rather than a simple “good” or “bad.”
2. “What’s something that made you smile today?”
A wonderful way to get them to relive a happy moment with you.
3. “Walk me through what your morning looked like.”
Picture yourself walking beside them, noticing the little moments.
4. “What’s something you’re really excited about right now?”
Children and teens light up when you show interest in what they’re looking forward to.
5. “Is there anything you’re a little worried about lately?”
Sometimes just being asked gives them the courage to share.
6. “What’s the funniest thing that happened to you recently?”
Laughter lowers walls and invites storytelling.
7. “Who do you like spending time with at school (or work)?”
Opens up conversations about friendships, teachers, and even crushes.
8. “Teach me something you learned this week!”
Children love feeling like they are the experts sometimes.
9. “What’s something you wish more people understood about you?”
This invites deep self-expression, especially for teenagers.
10. “If you could change one thing about today, what would it be?”
Helps them reflect without feeling like they are complaining.
11. “What’s a show, song, or book you’re loving right now?”
Even if you don’t know it, asking about it shows you care.
12. “What’s something you’re really proud of lately?”
Pride is often a quiet thing—help them bring it to light!
13. “If today was a movie, what would it be called?”
A playful, creative way to let them sum up their day.
14. “What’s something you’ve been curious about lately?”
Curiosity leads to great discussions—and teaches you what sparks their mind.
15. “Tell me about someone who made your day better recently.”
Highlights gratitude and relationships.
16. “If you could spend a whole day doing anything you wanted, what would it be?”
Gives you a window into their true passions and joys.
17. “Was there anything today that made you stop and think?”
Encourages them to share the deeper moments they might not otherwise mention.
18. “Tell me one thing that surprised you today.”
Surprises often reveal the sweetest (and sometimes funniest) parts of their day.
19. “If you had a magic wand, what would you fix or change around you?”
Dreaming big can reveal both worries and hopes.
20. “I love hearing your thoughts—what’s something you’ve been thinking about lately?”
Letting them know you love their mind is one of the greatest gifts you can give.
21. “What’s something new you’ve tried lately?”
Encourages bravery and new experiences.
22. “What’s been making you laugh a lot recently?”
Shared laughter builds connection faster than almost anything.
23. “Who’s someone you admire and why?”
Helps you understand who they look up to and why.
24. “What’s something that’s been bothering you, even just a little?”
Tiny troubles can build up—offering a safe place to share can make a big difference.
25. “If you could design your perfect weekend, what would it look like?”
Wonderful for hearing about their favorite activities and dream adventures.
26. “What’s the kindest thing someone’s done for you lately?”
Fosters gratitude and noticing kindness in everyday life.
27. “What’s the bravest thing you’ve done recently?”
Celebrate the small courageous acts that they might not even realize are brave.
28. “What’s something you’re looking forward to this month?”
Helps them look ahead with joy and optimism.
29. “If you could swap places with anyone for a day, who would it be?”
Their answer might surprise you—and reveal hidden interests!
30. “What’s something you wish you had more time for?”
You may learn what dreams or passions they quietly hold inside.
31. “Tell me about a time recently when you felt really proud of yourself.”
Let’s them savor a personal success they might otherwise downplay.
32. “If you could create your own holiday, what would it celebrate?”
Gets their imagination running—and often their values, too.
33. “What’s something you wish grown-ups understood better?”
This shows you’re willing to listen without judgment, a powerful gift.
34. “Is there anything you’ve been wanting to ask me?”
Children often have questions for us but may hesitate until we open the door.
35. “What’s a small thing you did today that made someone else’s day better?”
Helps them reflect on how they can be (and often already are) a blessing to others.
A Few Gentle Reminders
- Timing is everything. Sometimes, the best conversations happen when we’re not sitting face-to-face. Try chatting during a walk, cooking together, or even while doing puzzles or crafts.
- Listen more than you speak. Sometimes silence means they are thinking. Give them the time and space to find their words.
- Honor every share. Even if what they say seems silly or trivial, it matters to them—and because it matters to them, it should matter to us.
When we make time to ask thoughtful questions—and even more importantly, when we make time to truly listen—we don’t just learn about our grandchildren’s lives.
We plant seeds of trust, love, and deep connection that will grow for the rest of their lives.
And oh, what a beautiful garden that will b
