It’s tricky to get authentic conversations flowing with your kids and grandkids, especially tweens and teens.
One of the goals is to move you past the eye rolls and one-word answers.
Instead of the usual “How was school?” or “Did you finish your homework?”, try swapping in one of these more thoughtful prompts.
They give our kids and grandkids the floor, a chance to share their opinions, reveal what matters most to them, and spark connection in ways you may not expect.
• If you had to design a role model, what qualities would they have?
• Who’s your favorite teacher right now, and what makes them great?
• What do you hope people look up to you for when you’re older?
• Do you think money can buy happiness? Why or why not?
• What’s something you wish you knew more about?
• What’s something you wish I knew more about?
• What are you most proud of yourself for?
• What’s been one big turning point in your life so far?
• If money didn’t exist, what would you want to be paid in?
• Do grades help kids learn, or do they make it harder?
• Who in the world makes you feel the most loved? (You can’t pick me.)
• Who makes you feel the most heard? (You can’t pick me.)
• Who makes you feel the most understood? (You can’t pick me.)
• What’s something people often misunderstand about you?
• What’s something you really want to learn how to do?
• What do you look for in a friend?
• What do you look for in a relationship?
• Do you ever try to interpret your dreams?
• If you had to write a book, what would it be about?
• If I had to write a book, what do you think I should write about?
How To Use Them
Don’t feel like you need to ask all of these at once. Just swap out one of your “default” questions each day.
You’ll likely catch your child off guard … in a good way!
When kids don’t have a pre-planned answer, they often open up more than you expect.
These questions also show you’re not just checking in on tasks, you’re inviting them to think, share, and be heard. That’s where connection deepens.
Major tip: even if your child shrugs at first, stick with it. Over time, the consistency tells them you’re genuinely interested, and that’s when the magic happens.
Cheering you on.
Related Articles:
3 Simple Ways to Help Your Child & Grandchild Feel Like They Belong (Without Burning Yourself Out)
Top 3 Strategies to Create a Strong Sense of Belonging for Your Child and Grandchild
