I Tried These Conversation Starters With My Kids—And It Changed Everything

I will never forget how his eyes lit up. All year, I’d been asking my preschooler the same default question: “How was your day?” Only to be met with a quick, “Good!” before squirming out of my hug in search of Legos and snacks. But this particular day, I tried a different strategy. “Did you make anyone laugh today?” I asked. He stopped squirming, looked directly into my eyes, and said with such conviction, “YES!” before diving into a detailed story, complete with silly faces and all the things that make a 5-year-old giggle uncontrollably.

In that moment, I realized my son had plenty to tell me—I’d simply been asking the wrong questions. And so, I set off to become a collector of questions and conversation starters for families that actually get kids talking.

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In truth, my revelation changed more than just the way I talk to my kids (see also: the ever-popular marriage meeting). “How was your day?” is such a broad, monotonous question that, hardly ever elicits meaningful conversation whether you’re five or fifty. It’s stories that drive us—stories that spark core memories and bring a certain color and richness to our lives. And stories begin by asking the right questions.

But it doesn’t stop there.

How do you have a good conversation with family?

Even with the best conversation starters in your toolbox, there are a few more things to consider when it comes to engaging kids (and parents, for that matter).

First, Consider timing

I used to host a regular “snack and share” around the table after school and that worked well—for a time. But as schedules change and my kids get older, they’re more interested in playing, eating, watching a TV show, and eating again than they are sitting down for a chat with an adult. These days, dinnertime works better for us. Every family will be different, but know that if your child is hungry or tired, no one will appreciate a forced family moment.

When your child opens a window for conversation, you never know how long it will stay open. Take the opportunity.

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Second, look for the windows

Occasionally in parenting, there will be a window of opportunity to talk—really talk—to your kids. But here’s the kicker. This moment most often comes when you least expect it, or when you’re busy, or when you’re not paying attention. OR when you’re child is almost asleep and mentally, you’re already on the couch with a celebratory drink. The key is to immediately do the opposite: stop what you’re doing and pay attention. When your child opens a window for conversation, you never know how long it will stay open. Take the opportunity. This builds a bond of trust and connection—and shows your child you’re always available when they need you.

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Finally, consider the setting

If your kids have a hard time opening up or getting into a conversational flow, change it up. Perhaps your dinner table is more chaotic than calm. In that case, it’s probably not the best place to introduce a new family ritual. If the right question is a seed, then your setting is the soil—it should be a place where conversation can grow.

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Try throwing out a few conversation starters while you’re going for a walk or bike ride. Driving in a car is the perfect place to ask fun questions, especially when there’s a snack stash handy. When you get out in nature or go for a drive, it provides something else to focus on which tends to magically open the avenues for free-flowing dialogue.

Now that you have the tools, let’s dive into the questions.

Questions to Ask Kids After School

Try these questions when your kid gets settled in the car, when you get home (or after you wrap up homeschool), or even later at dinner. Mix ’em up or, if your child responds well to a particular question, make it part of your post-school ritual.

• Did you make anyone laugh today?
• Who made you laugh today?
• Who did you sit next to at lunch?
• What did you eat today?
• Did anyone get in trouble today?
• Who did you play with on the playground?
• Did you play any games at recess?
• What made you feel happy today?
• Did anything make you sad today?
• What is one thing you learned today?
• What did your teacher talk to you about today?
• What is your favorite thing about your teacher?
• Did you do anything that felt hard today?
• Was anyone kind to you today?
• Did you help anyone today?
• Did you try anything new today?
• If you were the teacher for the day, what would you do?

If the right question is a seed, then your setting is the soil—it should be a place where conversation can grow.

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Family Dinner Questions

Use these dinner conversation starters as a jumping-off point. You can take turns answering a single question around the table or give everyone a new question. There’s no need to rush from one to the next—the goal is simply communication. Remember to practice active listening, stay curious, and have fun.

• Highs and lows: share one high and one low from the day.
• What are you excited about for tomorrow?
• What’s the best thing about your family?
• Pick one person at the table and give them a compliment.
• What’s one thing you’re looking forward to?
• What is your least favorite chore?
• What do you think makes for a happy family?
• What is your favorite meal we have as a family?
• If you could invite anyone over for dinner, who would it be?
• What is one new thing you learned today?
• What made you laugh or smile today?
• Tell one person at the table what you like about them.
• Share one thing you’re grateful for.
• What’s your favorite family tradition?
• Choose three words to describe yourself.
• Where would you like to go on a family vacation?
• If you could switch places with your parents for the day, what would you do?
• What’s the hardest thing about being your age?
• What’s the best thing about being your age?

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Conversation Starters For Teens

We were all there once, so are teenagers such a mystery? When it comes to conversation, look for the windows and give them a gentle nudge when they crack open. Call out the good stuff, validate emotions, and help them navigate any problems or issues—but don’t do it for them. Simple, right?  

• What’s something good in your life right now?
• What’s something hard in your life right now?
• Who’s someone you look up to and why?
• What’s the last thing you Googled?
• How do you feel about social media?
• What’s something you wish adults understood about teenagers?
• What is something you would have told yourself five years ago?
• What do you like about school?
• What makes someone a good friend?
• Do you have any friends you’re worried about right now?
• What’s one thing you really like about yourself?
• What scares you most about the future?
• What excites you most about the future?
• What’s the best thing about being a teenager?
• What’s something you’re proud of?
• Has there ever been a question you wanted to ask me but haven’t?
• If you could relive one day of your life, what would it be?

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Fun Conversation Starters for Families

Stuck in a car for a long time? These fun questions and would-you-rathers are road trip gold. My recommendation: drive as far as the first gas station, let everyone choose one snack, then kick off the trip with a question before pulling out the screens.

• What’s your favorite word?
• If you met a genie, what three things would you wish for?
• What’s a word that always makes you laugh?
• Tell me your favorite joke.
• Would you rather shave your head or have a mohawk?
• You just put on the sorting hat: which Hogwarts House are you in?
• Would you rather lose social media or TV?
• If you could trade places with one person for a day, who would it be?
• If you were a superhero, what would be your power?
• If I gave you $100, where would you spend it?
• If you could only eat one food every day for the rest of your life, what would it be?
• If you could pick your own name, what would it be?
• If you had a time machine, where (or when) would you go?
• If you could be a character from any book or movie, who would you be?
• If you could have any pet, what would you pick?
• Would you rather live in the mountains or on the beach?
• If you could only watch one movie for the rest of your life, what would it be?
• Would you rather go on a cruise or a safari?
• If the sky rained food, what would you want it to be?
• If we all lived in a zoo, what animal would each person be?
• If you could make a new animal, what would it be?
• If there was a movie about you, what would it be called?
• Would you rather go to space or dive deep into the ocean?
• If you could make one of your toys come to life, which one would you pick?
• If you could live inside one TV show, what would it be?

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Getting To Know You Questions

Finally, these questions are good to have in your pocket for any occasion. Try them when you’re FaceTime-ing with out-of-town relatives or on a Saturday morning donut run. There’s always something new to discover, even about your own child—and vice versa.

• If you were invisible for a day, what would you do?
• What is your happiest memory?
• When was the last time you felt embarrassed?
• I wish I knew more about ______.
• Who is the nicest person you know?
• Describe your perfect day.
• What is your favorite book?
• When was the last time you changed your mind?
• Who is the funniest person you know?
• What makes you feel better when you’re scared?
• What are your favorite toys?
• What do you like about your favorite movie?
• When was the last time you felt embarrassed?
• Who is a famous person you admire?
• What helps you get out of a bad mood?
• Where is your favorite place to go?
• What do you do when you’re bored?
• What’s the best gift you ever received?
• What do you want to be when you grow up?
• What is one thing you’re really good at?
• What’s your favorite dessert?
• What is your favorite thing to wear?
• What is something you’d like to learn to do?

Final Thoughts (And How to Get Started)

Hosting meaningful conversations with your family doesn’t need to be some big overhaul in your routine. My favorite way to start anything at all is to begin with a small seed of change. Small is sustainable. So, what does that look like? Choose one question on the way to school. Give yourself three minutes to connect. Pick one day of the week for a family walk and talk. After all, the thing about seeds? They tend to grow.

(PS: Listening, reflecting, and seven more ways to encourage confidence in your kids.)