When Kids Won’t Open Up: Gamify Difficult Conversations

Andrew Ronald

Simirity Founder | Father of two

12th February, 2026

As a parent, it’s so painful when you can see from the look of your child’s face that they have a problem. Schoolwork challenges, friendship troubles, changes within their home environment. But when you ask directly, you face silence or a refusal to talk about it.

Of course, it’s not that they don’t want help, it’s just that having difficult conversations about these topics triggers their defences. They feel vulnerable, pressured, and may struggle to explain their thoughts and feelings. Even as adults we can still feel that desire to run off and hide from difficult conversations, but we’ve gotten better at managing our emotions and have learned the benefit of honest exchanges.

Thankfully, there is a way to gamify these difficult conversations, allowing parents to gain precious insights into the challenges their children face without them feeling interrogated. In fact, it’s fun, and offers a great way to strengthen the relationship with your child.

The solution is a carefully prepared version of ‘would you rather’, where targeted questions that parents carefully choose, are mixed in with regular questions.

Using Indirect Questions in Difficult Conversations

Children’s defences are easily triggered by direct questions such as, “Why don’t you like to spend time with your friends anymore?”

Indirect ‘would you rather’ questions are not asking them to discuss a specific situation, but are inviting them to explore hypothetical scenarios. Instead of putting them on the spot about their feelings, you’re creating a playful game where there are no wrong answers.

Here are a few example questions that can lead to deep discussions:

• Would you rather have someone trust you completely or think you’re really fun?
• Would you rather have more money for fun things or more time together as a family?
• Would you rather make mistakes in front of others or never try new things?

Hypothetical questions like these allow them to discuss the real challenges they’re facing without admitting that they have a problem. And their explanation of their answer can provide you with the insights you need to help them through it.

And it’s not just them sharing their answers. You can too. And by doing so, you can share your own thoughtful reasoning and experiences, to model the kind of honest answers you’re hoping to see from them.

In this guide, you’ll find 61 questions organised by common challenges: friendship issues, behaviour problems, emotional struggles, family changes, and school stress. Mix these with general questions so conversations feel fun.

NOTE: These questions help you start difficult conversations—they don’t replace professional help when children need it.

How to Use These Questions

Start by choosing 3-5 questions from whichever section feels most relevant to your child. It’s really important not to fire these questions at your child, one after another. Their defences will go up and you won’t get anywhere. Mix them with non-targeted questions (we have 300+ general “would you rather” questions to share with you).

Timing matters. Choose a moment when you’re already spending relaxed time together—driving somewhere, eating dinner, the bedtime wind-down. Not when you’re both stressed or rushing. Here are 7 occasions in family life where questioning games like these work well.

To encourage your child to open up, you might want to consider sharing your answer to the question first, at least to get them going. It also gives them time to consider their own answer. Of course, if your child it keen to share their answers then let them go right ahead. But it does make sense to share your answer too at some stage, to demonstrate that being vulnerable and honest is safe, and that there are no correct answers.

Your child’s answer is just the starting point of a deeper understanding into their thinking.

The learning only comes when you ask relevant follow-up questions like “Interesting choice—what made you pick that one?” Active listening is a must. Be fully present, pay attention to non-verbal cues and withhold your judgement. It’s also great to reflect back what you hear them say – paraphrasing what they just said confirms you understand them correctly and may encourage them to elaborate on the topic, offering further insights.

Remember: every question in this guide targets a specific childhood challenge. For best results, blend them with general fun questions so your child feels its a game, not an interrogation. It really can be very fun!

Don’t fall into these traps:

• Making it feel like an interview
• Jumping straight to advice or solutions
• Asking several serious questions consecutively
• Later weaponising their answers (“You said you value honesty and look at you now!”)

What you’re listening for:

• Which principles matter to them
• Personal stories that emerge during explanations
• How they react emotionally to different scenarios
• Recurring themes in their choices

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Questions for Friendship and Social Issues

Use these when:

• Friendship troubles are surfacing
• Your child’s feeling lonely
• They’re being excluded from their friend group
• They’re facing peer pressure situations
• They are struggling with social skills

The indirect advantage:

Children protect themselves by not admitting social struggles. Saying “I don’t have friends” or “They left me out” feels like accepting a shameful truth. So they deflect, minimise, or lie about it.

Hypothetical scenarios bypass this defence. Your child isn’t admitting anything—they’re just choosing between options. But their choices reveal everything.

Do they value quantity or quality in friendship? Authenticity or belonging? Confrontation or peace?

Listen for the stories that emerge during their explanations. “I didn’t talk to him about it because I knew he would get angry with me.” That’s not hypothetical—it’s a lived experience.

These questions also work for children who are doing the excluding. When they explain why they’d choose “being popular” over “including everyone,” you’re learning about the social pressures they feel and the choices they’re making.

Questions for ages 5-8:

1. Would you rather have one best friend or lots of friends who aren’t as close?
2. Would you rather be invited to every party but never have a best friend, or have one best friend who always chooses you first?
3. Would you rather tell a friend they hurt your feelings or pretend everything is fine?
4. Would you rather be really good at making friends or really good at keeping friends?
5. Would you rather play with someone everyone likes but is sometimes mean, or someone who’s always kind but doesn’t have many friends?

Questions for ages 9+:

6. Would you rather fit in with the popular group but hide parts of yourself, or be yourself and have fewer friends?
7. Would you rather be the friend everyone comes to with problems, or the friend who makes everyone laugh?
8. Would you rather confront someone who hurt you or let it go to avoid drama?
9. Would you rather be included in group chats where people gossip, or excluded but keep your integrity?
10. Would you rather have friends online who really get you, or local friends who don’t understand you as well?

Questions for both ages:

11. Would you rather tell an adult when someone’s being mean or try to handle it yourself?
12. Would you rather be the person who includes everyone or be part of the popular group?
13. Would you rather have a friend who’s fun but unreliable, or boring but always there for you?
14. Would you rather forgive a friend who hurt you or stay mad but protect yourself?
15. Would you rather be the leader in your friend group or let someone else lead?

Questions for Behaviour and Character

Use these for:

• Addressing lying patterns without accusations
• Handling defiance or disrespect without power struggles
• Teaching responsibility without nagging
• Building values without preaching

The strategic advantage:

Direct confrontation about behaviour problems typically goes one of two ways: denial (“I didn’t!”) or justification (“But you said…”). Neither leads anywhere productive.

These questions avoid that entirely.

You’re not accusing your child of lying—you’re exploring the idea of telling the truth versus lying. You’re not calling them irresponsible—you’re discussing choices and the consequences that follow.

Children reveal their thinking without feeling they’re being tested. And once you understand how they think about these issues, you can address the real problem rather than just the surface behaviour.

Questions:

1. Would you rather tell the truth and get in trouble, or lie and feel worried about being caught?
2. Would you rather do something hard that makes your family proud, or something easy that only makes you happy?
3. Would you rather admit you made a mistake right away, or hope no one finds out?
4. Would you rather be known as someone honest or someone clever?
5. Would you rather have lots of rules but know exactly what’s expected, or few rules but figure things out yourself?
6. Would you rather say sorry first even if you weren’t totally wrong, or wait for the other person to apologize?
7. Would you rather do the right thing when everyone’s watching, or when no one would ever know?
8. Would you rather have someone trust you completely or think you’re really fun?
9. Would you rather make your own choices and deal with consequences, or have parents decide everything for you?
10. Would you rather be popular by being someone you’re not, or unpopular but true to yourself?
11. Would you rather get away with something wrong but feel guilty, or get caught but feel relieved?
12. Would you rather share something even when it’s hard, or keep it to yourself to avoid conflict?

Moving deeper:

Treat their answers as helpful nuggets of information, not confessions.

When your child reveals how they think about honesty, responsibility, or integrity, resist the urge to correct. Instead, ask: “Why do you think that?” or “What would make someone choose differently?”

The goal isn’t agreement—it’s understanding. Once you understand how they think, you can help them think more deeply. When it feels natural, connect these hypothetical explorations to real experiences: “You said you’d rather do the right thing when no one’s watching. That must have been hard last week when…”

Questions for Big Feelings and Emotions

Use these for:

• Frequent meltdowns or mood swings that concern you
• Signs of anxiety you want to address
• Anger management issues you need to tackle
• Building emotional awareness in children who can’t name what they feel

Why hypothetical scenarios help:

Direct questions about emotions often fail: “Why are you so angry?” makes them angrier. “What’s making you anxious?” increases anxiety. “How do you feel?” gets met with “I don’t know” because they genuinely don’t.

These questions take a different approach.

You’re not asking them to analyse their current emotional state. You’re exploring how they prefer to handle feelings in general. And when you better understand their emotional wiring, you’re better able to help them.

Questions:

1. Would you rather feel really angry for 5 minutes and let it all out, or feel a little bit angry all day but stay quiet?
2. Would you rather talk about your feelings or do an activity to feel better?
3. Would you rather everyone know when you’re sad or keep it private?
4. Would you rather have a calm-down space at home or a special person to talk to when upset?
5. Would you rather scream into a pillow when angry or talk to someone about it?
6. Would you rather feel worried about something small all day, or very worried about something big for a short time?
7. Would you rather cry when you need to even if people see, or hold it in until you’re alone?
8. Would you rather know exactly why you’re upset or just feel better without understanding why?
9. Would you rather handle scary feelings on your own or get help from family?
10. Would you rather feel all your feelings strongly or feel them less intensely?
11. Would you rather people ask if you’re okay when you’re upset, or leave you alone?
12. Would you rather feel nervous before trying something new or feel disappointed for not trying?

When to seek help:

These questions help you understand your child’s emotions, so you can support them through challenges. They don’t address serious concerns like persistent anxiety, depression symptoms, self-harm thoughts, or trauma responses.

If their answers reveal safety concerns or patterns beyond typical childhood emotions, seek professional support.

Questions for Family Changes and Challenges

Use these for:

• Major transitions your child won’t discuss: new sibling, divorce, house move, blended family formation
• Financial stress affecting the family
• Loss or grief they’re processing
• Any significant change they’re struggling with but avoiding

Why indirect questions work here:

Perhaps it’s a new sibling, a change of home or the separation of parents that troubles them, but they say they’re fine even when they’re not, because they don’t want to stress or hurt you.

Hypothetical questions remove that burden.

They’re not telling you they hate the idea of moving home—they’re just choosing between “bigger bedroom in new house” versus “current bedroom forever.” But their choice and explanation reveal how they actually feel about the change.

There’s no “right” answer to “Would you rather things stay the same or have exciting changes even if they’re hard?” Your child can express resistance to change without worrying about hurting a parent’s feelings.

Questions:

1. Would you rather have a bigger bedroom in a new house or your current bedroom here forever?
2. Would you rather spend more time with just one parent or less time with both together?
3. Would you rather family do more activities together or have more free time alone?
4. Would you rather things stay exactly the same or have exciting changes even if they’re hard?
5. Would you rather know about big changes in advance or find out when they happen?
6. Would you rather have a new baby sibling or stay the youngest/only child?
7. Would you rather visit grandparents more often but for shorter times, or less often but longer visits?
8. Would you rather have two homes (if divorce) or one main home?
9. Would you rather talk about hard family things or pretend everything’s normal?
10. Would you rather have family traditions stay the same or create new ones?
11. Would you rather have more money for fun things or more time together as a family?
12. Would you rather adults tell you everything that’s happening or protect you from worries?

Creating stability through conversation:

Use their answers to shape how you handle the transition. If they’d “rather know about changes in advance,” give them as much warning as possible. If they’d “rather pretend everything’s normal,” they might need smaller doses of difficult conversations.

Acknowledge their feelings as valid. Involve them appropriately in decisions where possible. Maintain familiar routines even as other things change.

Consider documenting this transition period in Simirity family journal—capturing how everyone’s feeling over time can help everyone process the changes.

Questions for School and Achievement

Use these for:

• When they are stressed about tests
• Homework challenges
• Unhealthy perfectionism
• School avoidance
• Academic pressure—whether from school, themselves, or you

The strategic value:

These questions let you explore their relationship with achievement, effort, and learning without requiring confession. Do they prioritise grades over understanding? External validation over internal satisfaction? Avoiding failure over attempting challenges?

Their answers show you whether pressure is coming from internal perfectionism or external expectations, whether they’re motivated by curiosity or fear, and whether they view mistakes as learning opportunities or as personal failures.

Questions:

1. Would you rather get perfect grades but feel stressed, or good grades but enjoy learning?
2. Would you rather understand things right away or struggle at first but feel proud figuring it out?
3. Would you rather be the smartest in class or have the most friends?
4. Would you rather try something new and possibly fail, or stick with what you’re good at?
5. Would you rather have less homework and learn less, or more homework but learn more?
6. Would you rather get help when struggling or figure it out independently?
7. Would you rather be known for being smart or being kind?
8. Would you rather make mistakes in front of others or never try new things?
9. Would you rather have high expectations and sometimes disappoint people, or low expectations you always meet?
10. Would you rather compete with classmates or collaborate with them?

Following up strategically:

Watch for perfectionism patterns: choosing “perfect grades but stressed” or “never try rather than make mistakes” signals unhealthy pressure. Validate that struggle is part of learning, not failure.

Making This a Habit

Start this week

Hopefully by now you have already identified a number of questions where you felt curious how your child would answer. Note those down and add to them regular questions from our “Would You Rather” collection.

Start with lighthearted, playful questions and be sure to share your answers too, modelling the honesty and storytelling that you would like from them.

Make it a family ritual

Rather than playing this game once and being done with it, why not make it a regular thing with a ritual that fits neatly into your family life? Here are 7 ideal moments in busy family lives to engage your children with would you rather questions.

Documenting what you learn

With each passing day, your children are changing. Over time, how many precious details will be lost?

As parents, we try to capture these changes in photos and videos, but there’s so much going on in their minds that you simply can’t capture visually. That’s where the Simirity Family Journal can help, providing you with a private place to track changes beyond the visuals and capture their personality and thoughts and ideas at every stage of life.

Within the app, each child has their own profile, and as their parent, you can create unlimited stories about them and upload all kinds of media into them. You could even make an audio recording of a session where you ask “would you rather” questions and capture their answers forever. What a treat it will be to re-listen to such conversations in years to come.

And stories like these are not just for you and your children’s benefit —family beyond your home, such as grandparents, aunts and uncles, would get to know your children so much better.

Conclusion

Indirect questions help lower children’s natural defences that prevent them from opening up and sharing their honest views. Hypothetical scenarios, as provided by ‘would you rather’ questions, let children explore real feelings in a stress-free way.

This approach works when you’ve identified a problem your child won’t discuss. Alternatively, if you are not sure what their problem relates to, asking them a wide range of targeted questions may help you identify what on their mind.

Don’t worry about being perfect, and you don’t need to use all of the questions included in this post. Find the right moment in your family life when your child is feeling relaxed and simply get started. Who knows where the conversation will lead.

At the very least, it’ll be a fun conversation, not a difficult conversation.

For 300+ general questions to mix with these targeted questions, see our complete Would You Rather guide.

Simirity—because one day, you’ll wish you’d captured their stories.

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