Good Questions to Ask Teens
Thoughtful questions to connect with teenagers, understand their world, and foster meaningful conversations beyond small talk.
1What's something you're really proud of that you don't get enough credit for?
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What's something you're really proud of that you don't get enough credit for?
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Why this works
Validates their accomplishments and opens space for them to share achievements that matter to them.
2If you could change one thing about school, what would it be?
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If you could change one thing about school, what would it be?
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Why this works
Invites their perspective on education and shows you value their opinions about their daily experience.
3Who do you feel really understands you?
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Who do you feel really understands you?
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Why this works
Reveals their support system and helps you understand their relationships and connections.
4What's something you want to learn that isn't taught in school?
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What's something you want to learn that isn't taught in school?
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Why this works
Uncovers their interests and passions beyond academics, showing you care about their holistic development.
5What's the biggest challenge you're facing right now?
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What's the biggest challenge you're facing right now?
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Why this works
Opens the door for them to share struggles and creates an opportunity for support.
6If you could have dinner with anyone, living or dead, who would it be and why?
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If you could have dinner with anyone, living or dead, who would it be and why?
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Why this works
Reveals their role models, interests, and values through their choice and reasoning.
7What do you think adults misunderstand most about teenagers?
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What do you think adults misunderstand most about teenagers?
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Why this works
Gives them a voice to address stereotypes and helps you see their perspective on generational differences.
8What's your favorite way to spend free time?
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What's your favorite way to spend free time?
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Why this works
Shows genuine interest in their hobbies and how they choose to recharge.
9What's something you believe that most of your friends don't?
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What's something you believe that most of your friends don't?
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Why this works
Explores their individuality and willingness to think independently from peer influence.
10What does success mean to you?
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What does success mean to you?
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Why this works
Helps you understand their values and aspirations beyond conventional markers like grades or popularity.
11If you could solve one problem in the world, what would it be?
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If you could solve one problem in the world, what would it be?
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Why this works
Reveals their social awareness and what causes they care deeply about.
12What's something you've changed your mind about recently?
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What's something you've changed your mind about recently?
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Why this works
Shows that evolving opinions is healthy and encourages reflective thinking.
13What makes you feel most confident?
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What makes you feel most confident?
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Why this works
Identifies sources of their self-esteem and areas where they feel competent.
14What's the best advice anyone has ever given you?
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What's the best advice anyone has ever given you?
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Why this works
Uncovers wisdom they've internalized and the people who have influenced them positively.
15What are you looking forward to in the next year?
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What are you looking forward to in the next year?
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Why this works
Shifts focus to the future and creates space for them to share hopes and excitement.
16What's something you wish your parents or teachers understood about you?
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What's something you wish your parents or teachers understood about you?
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Why this works
Opens honest communication about how they feel misunderstood and what support they need.
17What app or technology could you not live without, and why?
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What app or technology could you not live without, and why?
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Why this works
Meets them in their digital world and helps you understand how they connect and express themselves.
18What's a fear you have about the future?
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What's a fear you have about the future?
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Why this works
Creates space for vulnerability and allows you to address concerns or provide reassurance.
19What's something you want to be better at?
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What's something you want to be better at?
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Why this works
Shows they have growth mindsets and opens conversations about how you can support their development.
20If you could describe your perfect day, what would it look like?
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If you could describe your perfect day, what would it look like?
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Why this works
Reveals what brings them joy and helps you understand their ideal way of spending time.
Best Practices for Connecting with Teens
Expert tips and techniques for getting the most out of these questions.
Best Practices
Listen Without Fixing
Resist the urge to immediately solve their problems. Sometimes they just want to be heard and understood.
Avoid Judgment and Lectures
Create a safe space where they can share honestly without fear of criticism or a sermon.
Respect Their Privacy
Don't pry or demand details. Let them share at their own comfort level.
Meet Them Where They Are
Engage with their interests—whether it's gaming, music, or social media—rather than dismissing them.
Conversation Sequences
The Identity Exploration Sequence
The Support-Building Sequence
The Future-Focused Sequence
Common Pitfalls
Don't Dismiss Their Problems as 'Small'
What feels minor to you might be monumental to them. Validate their feelings regardless of scale.
Don't Compare Them to Others
Avoid statements like 'When I was your age...' or 'Your sibling never had this problem.' It shuts down conversation.
Don't Interrogate
Space out questions naturally within conversation. Rapid-fire questions feel like an investigation.
Don't Break Their Trust
If they share something in confidence, honor that unless safety is at risk. Betraying trust damages relationships.