35 Questions to Ask Your 9-12 Year Old About Fun and Play
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Around ten or eleven, some children decide that play is childish to admit to. Not to stop doing, just to stop mentioning. Which is a shame, because play is still doing most of the developmental work, and it is still where you learn the most about them in the least threatening way.
These questions give them permission. They treat games, invented worlds and messing about as legitimate subjects rather than as things you have graciously not confiscated yet. Several ask about rules and rule breaking inside games, which is where children this age reveal their thinking about fairness with no defences up at all.
If your child has gone quiet on the serious questions, start here. The route back to the harder conversations usually runs through the easy ones, and it is very difficult to be guarded while explaining the rules of something you invented.
Each question comes with what to listen for and what the answer tells you.
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1“What's a game you could play for hours and never once get bored of?”
What to listen for
An immediate, enthusiastic answer shows you where they find real flow, that deep, absorbed kind of fun that isn't about winning or being watched.
If the game involves other people, it tells you play is tied up with connection for them right now; if it's a solo game, they might be craving stretches of time where nobody's managing them.
A vague 'I don't know, just games' might mean they haven't had much unstructured time lately to even notice what hooks them, worth carving out more of that this week.
What this tells you
This shows you what genuine, pressure-free fun looks like for your child right now.
See this question on its own page (day 8) -
2“Is there a made-up game from when you were little that you still think about sometimes?”
What to listen for
A fond, detailed answer shows they still hold onto their younger imagination fondly, even while working hard these days to seem more grown-up.
If they laugh it off as 'so babyish' before telling you anyway, that's them navigating the tension between wanting to seem mature and still loving something playful, reassure them that's not a contradiction at all.
If they say they don't remember any, that's okay, you can describe one you remember them loving and see if it sparks something.
What this tells you
This shows you that your child's inner world still has room for wonder even as they push toward feeling older.
See this question on its own page (day 18) -
3“When's the last time you laughed so hard it actually hurt?”
What to listen for
A vivid retelling, complete with reenactment, shows this is a genuinely treasured memory, those big, uncontrollable laughs are some of the most bonding moments kids have.
If the story involves you or the family, that's a strong signal home still feels like a place of real joy, not just rules and routines.
If they can't remember one recently, that's worth noting gently, it might just mean life's felt more serious lately, and a little more silliness could do everyone good.
What this tells you
This shows you where real, uncomplicated joy shows up most in your child's life right now.
See this question on its own page (day 28) -
4“Is there a sport or game you wish you were just naturally better at?”
What to listen for
An honest answer shows they're comfortable admitting a gap between where they are and where they want to be, that vulnerability is worth meeting with encouragement, not immediate tips.
If they sound frustrated rather than just wistful, that's worth exploring further, it might mean comparison to others (siblings, teammates) is weighing on them more than the skill itself.
If they insist they're fine with everything as is, that's worth accepting at face value, not every kid needs to want to improve at something to feel good about themselves.
What this tells you
This shows you where your child feels a gap between their ability and their ambition, and how that gap sits with them.
See this question on its own page (day 38) -
5“What's something you like building or making just for the fun of it, with no real goal?”
What to listen for
An enthusiastic answer shows they know how to create just for the joy of it, without needing a prize, a grade, or an audience, that's a rare and valuable kind of freedom to protect.
If they describe getting so absorbed they lose track of time, that's real flow, worth making more space for regularly, since it's genuinely restorative for kids.
If they say they don't really make things, that's not a failure, just an invitation to leave some unstructured supplies around and see what happens without any pressure attached.
What this tells you
This shows you whether your child still has room in their life for creating purely for its own sake.
See this question on its own page (day 48) -
6“What's your favorite way to spend a totally rainy, stuck-inside afternoon?”
What to listen for
A quick, specific answer shows they know how to keep themselves content without needing constant entertainment from you or a screen, a good, self-sufficient skill.
If the answer involves someone else in the house, that tells you being stuck inside still feels best when shared, not just tolerated, a nice thing to lean into more often.
If they say they'd just be bored, that's a fine, honest answer, not every kid has a ready-made rainy day ritual, and you could build one together.
What this tells you
This shows you what genuinely comforts and occupies your child when the world outside isn't an option.
See this question on its own page (day 58) -
7“What's something you love imagining or pretending, even if you'd never tell your friends about it?”
What to listen for
If they share something rich and specific, they trust you with the private, unfiltered part of their mind, that's a big deal at this age when kids start guarding their inner world more.
If they laugh it off or say "that's babyish," gently let them know imagination doesn't have an age limit and you're not going to judge it.
If they insist they don't do that anymore, that could just be true, or it could mean they've learned to keep that part private, either way, no need to dig further tonight.
What this tells you
This tells you how much of their private inner world they're willing to let you see right now.
See this question on its own page (day 68) -
8“What's your favorite thing to do indoors on a totally boring day?”
What to listen for
If they describe something they do alone happily, they've found a real source of self-soothing and independence that doesn't need anyone else's input, that's healthy.
If everything they mention involves other people, that's not a problem, but it's useful to know they may need more encouragement building comfort with their own company too.
If they say they're just bored and don't know, that's a normal answer for this age, no need to read anything deep into it.
What this tells you
This tells you how comfortable they are entertaining themselves and finding their own contentment without outside help.
See this question on its own page (day 78) -
9“What's the funniest thing that's happened to you lately?”
What to listen for
If they tell the story with real energy, they feel comfortable being fully expressive and silly in front of you, which is a great sign of ease in the relationship.
If they can't think of anything, they might just be having a low-energy day, or humor might be something they save mostly for friends, either is fine.
If the story involves someone else entirely, notice who that is, it often points to who currently makes their days lighter.
What this tells you
This tells you how much lightness and joy is showing up in their daily life right now, and who's helping create it.
See this question on its own page (day 88) -
10“Do you have a game you've invented with rules only you really know?”
What to listen for
If they describe it enthusiastically, that game is a genuine expression of their own creativity and control, a space where they get to be the one who makes the rules.
If they seem shy about it, gently make clear that made-up games are worth just as much as store-bought ones, maybe more.
If they say they don't really make up games, that's fine, some kids express that instinct through building or drawing instead, so keep an ear out elsewhere.
What this tells you
This tells you where they get to feel fully in charge and creative on their own terms, without anyone else's rules applying.
See this question on its own page (day 98) -
11“What's your favorite outdoor game or thing to do outside?”
What to listen for
If they answer with real enthusiasm, that activity is a genuine outlet for their energy and freedom, worth protecting time for regularly.
If they mention doing it mostly with specific people, notice who those people are, it tells you who they associate with feeling free and unrestrained.
If they say they don't really have one, that's useful to know, it might be worth introducing more unstructured outdoor time to see what clicks.
What this tells you
This tells you where they get to feel physically free and unrestrained, which matters as much as any quiet, indoor comfort.
See this question on its own page (day 108) -
12“What's a joke or a bit that's become a total family favorite?”
What to listen for
If they light up telling it, that shared joke is real evidence of belonging and warmth inside the family, a strong, positive sign.
If they can't think of one, that's worth noting gently, it might be a nudge to build more of that shared silliness intentionally.
If they mention a joke that's actually at someone's expense, use it as a soft opening to check whether it still feels fun to everyone involved.
What this tells you
This tells you how much shared joy and inside connection currently exists inside the family, in the small, silly moments.
See this question on its own page (day 118) -
13“What's your favorite memory from a family game night?”
What to listen for
A quick, happy memory means those shared moments are landing exactly as intended, they feel closest to the family during ordinary fun, not just big events.
If they bring up a moment where they won, or where everyone laughed at the same thing, notice which one it is, winning matters differently to different kids, and it tells you what makes them feel good in front of others.
If they can't remember one, that's useful information too, maybe game nights have gotten rare or tense lately and it's worth planning one soon.
What this tells you
This shows what kind of shared moments actually make them feel like they belong in this family.
See this question on its own page (day 128) -
14“What's the silliest thing you and a friend do together that would make no sense to anyone else?”
What to listen for
An easy, enthusiastic answer shows they've built a real private world with this friend, which is a strong sign of a secure, comfortable friendship.
If they seem a little shy sharing it, that's normal, inside jokes are personal, and being asked to explain them can feel like giving away something precious.
If they say they don't really have one, that might be worth a gentle follow-up about who they'd want that kind of silliness with.
What this tells you
Having a shared private joke with someone shows they know what real, easy closeness feels like.
See this question on its own page (day 138) -
15“What's a card or board game you never get tired of playing?”
What to listen for
An immediate answer with real enthusiasm shows this game is tied to good memories, not just entertainment, ask who they usually play it with, since that name matters too.
If they mention wanting to play it more often, that's a direct, easy request you can actually act on this week.
If they say they're tired of all of them, that might just mean it's time to learn something new together, a fun, low-stakes way to spend time.
What this tells you
This shows what kind of shared fun genuinely recharges them, which is useful for planning real connection time.
See this question on its own page (day 148) -
16“What's a made-up story you like telling, even if you've told it a hundred times?”
What to listen for
Genuine enthusiasm about retelling it shows they have a rich inner imagination they enjoy sharing, encourage them to tell it again, even if you've heard it before.
If the story has a recurring character or world, that's a sign of a whole private universe they've built, worth asking more questions about, since it clearly matters to them.
If they say they don't really make up stories, ask about a favorite daydream instead, not every imaginative kid tells stories out loud.
What this tells you
This shows the shape of their imagination and how much they enjoy inviting others into it.
See this question on its own page (day 158) -
17“What's a game where you just make up the rules as you go along?”
What to listen for
An enthusiastic description shows they enjoy having creative control and flexibility, not just following someone else's structure, that's healthy independence showing up through play.
If they describe playing this with someone else, notice how they negotiate the rules together, that's a real window into how they handle shared control and compromise.
If they say they always play by fixed rules, that's fine too, ask if they'd ever want to try inventing one, which can open up a fun new activity together.
What this tells you
This shows how comfortable they are creating their own structure instead of just following what's already set.
See this question on its own page (day 168) -
18“What's the last thing you built or made completely out of nothing?”
What to listen for
An excited, detailed description shows real creative confidence, they trust their own ideas enough to bring them into the world without needing instructions.
If they mention making it for someone else or to show someone, that tells you creating things is also how they connect and seek approval right now.
If they can't think of anything recent, that might just mean their days have been busier with structured activities lately, worth carving out some open-ended time this week.
What this tells you
This shows how much room they currently have to create freely without a set outcome in mind.
See this question on its own page (day 178) -
19“What's a physical trick or move you're trying to get good at right now?”
What to listen for
If they describe something specific and show real determination, even through failed attempts, they're building confidence in their own body and effort, they need you to notice the trying, not just the landing.
If they seem embarrassed or say they've given up on it, they might need permission to be bad at something in front of people without it meaning anything about them.
If they say "I don't know," ask about something physical they've done recently, a bike trick, a dance move, a sports skill, to jog it loose.
What this tells you
Their answer reveals how comfortable they are being a beginner at something in front of others.
See this question on its own page (day 188) -
20“What's a family joke that never stops being funny to you, no matter how many times we say it?”
What to listen for
If they immediately know the one and start laughing just talking about it, that inside joke is doing real work, it's a marker of belonging that's theirs, unique to this family, and worth keeping alive on purpose.
If they can't settle on just one, let them list a few, that's a sign humor is a real language of closeness in your house.
If they say "I don't know," bring one up yourself and watch their face; they'll usually correct you with the real favorite.
What this tells you
This shows you which piece of shared history has actually become part of their sense of belonging.
See this question on its own page (day 198) -
21“What's your favorite way to be silly with the whole family at once?”
What to listen for
If they light up describing a specific moment, a dance, a voice, a game everyone plays along with, that shared silliness is doing real work building their sense that this family is fun to belong to, not just functional.
If they say the family doesn't really do that, take that as useful information rather than a criticism, it might be worth creating more low-stakes silly moments on purpose.
If they say "I don't know," bring up a specific memory of everyone laughing together and ask if they remember it too.
What this tells you
This shows you whether lightness and play feel like a normal, expected part of family life to them.
See this question on its own page (day 208) -
22“Is there a game in our family that only we understand the rules to?”
What to listen for
If they can describe it in detail, including the made-up rules that wouldn't make sense to anyone else, that shared language is a strong sign of belonging, it's proof this family has its own culture that's theirs.
If they say there isn't one, that's a nudge to invent a tradition together, not a sign anything's wrong.
If they say "I don't know," describe a game you remember playing together and ask if they remember the made-up rule that came with it.
What this tells you
This tells you how much of their sense of belonging is tied to inside knowledge only your family shares.
See this question on its own page (day 218) -
23“What's something you do to entertain yourself when there's no screen around at all?”
What to listen for
If they can name a real activity, building, drawing, making up stories, going outside, that's a sign they've developed their own internal resourcefulness, which is worth naming as a strength, not just luck.
If they say they get bored and can't think of anything, that's common and not alarming, ask what they used to do before screens were an option, which sometimes unlocks an old favorite.
If they say "I don't know," ask about the last long car ride or waiting room and what got them through it.
What this tells you
This tells you how much they can generate their own fun rather than needing it handed to them.
See this question on its own page (day 228) -
24“What was the last game night that got a little too competitive?”
What to listen for
If they can laugh about it now and describe what happened, that's a sign they can look back on intense feelings with some perspective, which is a valuable emotional skill.
If they still seem bothered by how it went, or blame themselves or someone else pretty seriously, that's worth gently unpacking, ask what would make the next game night feel more fun for everyone.
If they say "I don't know," describe one you remember and ask for their side of it.
What this tells you
Their answer shows you how they handle the gap between wanting to win and keeping relationships intact.
See this question on its own page (day 238) -
25“What's your actual favorite thing to do at recess right now, not last year, right now?”
What to listen for
The emphasis on 'right now' matters, it invites them to update you on something that shifts fast at this age. If they describe a specific group or game, listen for whether they sound like they belong there naturally or like they're working to keep their spot.
If the answer has changed from what you'd expect (say, from running around to just talking with friends), that's a real signal of them growing into a slightly older version of themselves, wanting more say in how they spend unstructured time.
If they say recess is boring or they wander alone, don't jump to fix it immediately, ask one more soft question first, like 'is that by choice or does it feel kind of lonely?'
What this tells you
This tells you how connected and in-control they currently feel during the one part of their school day nobody structures for them.
See this question on its own page (day 248) -
26“Do you and [sibling's name] have a running joke that's just yours? What is it?”
What to listen for
A quick, easy answer with real detail tells you the sibling bond has its own private language, which is a strong sign of security between them, that's worth celebrating out loud. Ask them to explain the joke even if it doesn't make sense to you; the explaining itself deepens the connection.
If they hesitate or say 'not really,' that's useful without being alarming, sibling closeness ebbs and flows, and this just tells you where things stand right now, not where they'll stay.
If the 'joke' is actually a jab or something that stings one of them, listen for tone, sometimes what's framed as funny is doing double duty as a way to express real annoyance.
What this tells you
This shows you the current state of their private world with a sibling, whether it's a source of comfort or something more strained right now.
See this question on its own page (day 258) -
27“What's a recipe you actually love helping make? What's your job when we make it?”
What to listen for
If they describe a specific role they always take (stirring, measuring, being the taste-tester), that's them showing you a place where they feel genuinely useful and trusted, which matters more than the food itself. Notice the pride in their voice if they mention doing something more advanced than you'd expect, that's a bid for more responsibility in other areas too.
If they say they don't really have a job or just watch, that's a gentle nudge to give them a real task next time, kids this age want to contribute, not just observe.
If they mention wanting to try a step they're not allowed to do yet (like using a knife or the stove), take that seriously as a real signal of wanting more trust, not just pushing a boundary for its own sake.
What this tells you
This tells you whether they currently feel like a real contributor in family routines or more like a bystander who's along for the ride.
See this question on its own page (day 268) -
28“What's the best game you can remember either winning or losing really gracefully?”
What to listen for
If they describe winning graciously (not rubbing it in, or helping the other person feel okay), that shows real emotional maturity around competition. If they describe losing gracefully, listen for how they got there, did someone help them reframe it, or did they find that strength on their own? Either way it's worth naming clearly as a real strength.
If they can only think of times they handled it badly, don't dwell on that as a failure, ask what they'd do differently now, which turns it into a growth story instead of a regret.
If competition seems to be a sore spot generally, that's useful to know for how you frame games and comparisons at home going forward.
What this tells you
This tells you how they currently handle the emotional swing of winning and losing, which reflects a lot about their overall sense of security in themselves.
See this question on its own page (day 278) -
29“Do you have a way of turning a boring chore into something more like a game? What is it?”
What to listen for
If they describe a specific trick, racing the clock, making up a story, turning it into a challenge, that's a sign of real resourcefulness and a healthy relationship with things they don't love doing, which will serve them well for life. Celebrate the cleverness of it specifically, since that reinforces their own problem-solving instincts.
If they say chores are just boring and there's no trick, that's honest, you could offer one of your own as a lighthearted suggestion, not a correction.
If they mention doing this with a sibling to make a shared chore more fun, that's worth noting as a nice sign of teamwork between them.
What this tells you
This tells you how they cope with things they don't enjoy, and whether they've found their own way to bring a sense of play into daily obligations.
See this question on its own page (day 298) -
30“What's something you love building or drawing when you're bored and nobody told you to?”
What to listen for
The things kids make with no assignment attached are the truest window into what actually interests them, pay attention to whether it's the same thing every time (a sign of real focus) or always something different (a sign of a wide-open, exploring mind).
If they get genuinely animated describing it, that's them telling you they need more unstructured time, not more scheduled activities, to feel like themselves.
If they say they don't really build or draw anything, ask what they do instead when they're bored, everyone has some private default mode, even if it's not art.
What this tells you
What they create with no one watching shows you who they are when they're not performing for anyone.
See this question on its own page (day 308) -
31“What's the funniest family memory you can think of right now?”
What to listen for
The memory they pick first is rarely random, it usually involves a moment they felt fully relaxed and completely part of the group, with no pressure to be anything other than themselves.
If they tell it in a lot of detail and laugh while retelling it, that's them showing you this memory is a genuine comfort spot they return to, a sign of feeling securely connected to the family.
If they need a minute to think, that's fine; you can offer one of your own favorites first to jog things loose.
What this tells you
The memory they reach for first shows you where they feel most safely and joyfully connected to this family.
See this question on its own page (day 318) -
32“What's your favorite way to spend time completely alone?”
What to listen for
If they describe something they genuinely look forward to, that's a healthy sign, they're learning that their own company can be enjoyable, not just something to escape through screens.
Notice whether their answer is about resting (reading, daydreaming) or creating (drawing, building), both are fine, but it tells you what kind of alone time actually refuels them.
If they say they never want to be alone, that's worth noting gently, some kids need more help learning that solitude can feel good, not lonely.
What this tells you
This reveals whether they're developing a comfortable, restorative relationship with their own company.
See this question on its own page (day 328) -
33“What's a trick shot or move you keep practicing over and over to finally nail it?”
What to listen for
The fact that they keep coming back to something difficult, without being told to, is a strong sign of real internal drive, notice how they talk about failing at it, whether it discourages them or fuels them.
If they describe small improvements with pride, that's them learning that mastery comes in increments, a lesson that will serve them in everything else too.
If they say they've given up trying to nail something, ask what made them stop, sometimes it's boredom, sometimes it's discouragement, and those need very different responses from you.
What this tells you
This shows you how they handle the gap between wanting to be good at something and not being there yet.
See this question on its own page (day 338) -
34“What's a game that's actually more fun with just two people than with a big group?”
What to listen for
Kids who gravitate toward one-on-one games are often telling you they value depth of connection over the energy of a crowd, that's useful to know when planning how they like to spend time with friends.
Listen for who they picture playing it with, that person is probably someone they feel especially close and comfortable with, worth noting as an important relationship.
If they say they always prefer big groups, that's telling too, it may mean they draw energy from a crowd and feel most alive when there's a lot going on around them.
What this tells you
This reveals whether they recharge more through close one-on-one connection or wider group energy.
See this question on its own page (day 348) -
35“Is there a family tradition built around a specific game or sport?”
What to listen for
If they describe this with real enthusiasm, it shows that shared play is one of the strongest threads connecting them to the family, not just a pastime but a genuine source of belonging.
Listen for whether the joy comes from competing, from the ritual itself, or from being together regardless of the game, that tells you what to lean into more when planning family time.
If no tradition comes to mind, ask what game they wish became a tradition, that's an easy, concrete way to actually start one.
What this tells you
This shows you how shared play has become a genuine source of belonging for them within the family.
See this question on its own page (day 358)
How to use these
One a night, not ten in a row. This is a conversation, and a list read out loud is an interview.
Ask it while something else is happening. In the car, drying dishes, walking the dog. Eye contact raises the stakes, and the side of the head is easier to talk to than the front of it.
Ask, then stop talking. The useful part almost always arrives after the silence you were tempted to fill.
Do not correct the answer. The moment an answer gets graded, the next one gets managed.
When the answer is "I don't know"
"I don't know" is rarely the end. Most of the time it means "I have not thought about it yet" or "I am checking whether this is safe to answer". Wait five seconds without filling the gap. If it still does not come, take the pressure off and answer it yourself first, out loud, about you. A child who hears you go first learns that the question is an invitation and not a test, and the answer usually turns up later, when you are not looking at them.
Other topics for this age
ConnectionFeelingsWho They AreFamilyArgumentsRules and LimitsRight and WrongGrowing UpDreams and the Future
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