Middle School Questions to Ask
Age-appropriate conversation starters that help middle schoolers open up, build friendships, and develop social skills during this crucial developmental stage.
1What's the best thing that happened to you this week?
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What's the best thing that happened to you this week?
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Why this works
Simple positive opener that encourages sharing good news and helps build rapport through positive experiences.
2If you could have any superpower, what would it be and why?
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If you could have any superpower, what would it be and why?
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Why this works
Fun, imaginative question that reveals personality traits and values while being universally engaging for this age group.
3What's your favorite subject in school and what makes it interesting to you?
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What's your favorite subject in school and what makes it interesting to you?
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Why this works
Shows interest in their academic life while allowing them to express passion and explain their learning preferences.
4If you could travel anywhere in the world, where would you go and what would you do there?
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If you could travel anywhere in the world, where would you go and what would you do there?
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Why this works
Opens up discussion about interests, dreams, and cultural awareness while being exciting and aspirational.
5What's something you're really good at that you're proud of?
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What's something you're really good at that you're proud of?
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Why this works
Builds self-esteem by encouraging them to share accomplishments and helps you learn about their talents and interests.
6Who is someone you really look up to and what do you admire about them?
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Who is someone you really look up to and what do you admire about them?
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Why this works
Reveals their values and role models while encouraging reflection on positive character traits they aspire to.
7What's the funniest thing that happened to you recently?
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What's the funniest thing that happened to you recently?
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Why this works
Light-hearted question that encourages storytelling and helps build connection through shared laughter.
8If 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
Gives them a safe space to express opinions about their environment while showing you value their perspective.
9What's something new you've learned recently that surprised you?
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What's something new you've learned recently that surprised you?
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Why this works
Encourages curiosity and learning while allowing them to share knowledge and show intellectual growth.
10What do you like to do when you have free time?
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What do you like to do when you have free time?
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Why this works
Reveals hobbies and interests while giving insight into how they choose to spend their personal time.
11If you could have dinner with anyone, living or dead, who would it be and what would you talk about?
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If you could have dinner with anyone, living or dead, who would it be and what would you talk about?
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Why this works
Encourages deeper thinking about interests and values while being an engaging hypothetical scenario.
12What's something that makes you feel really happy or excited?
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What's something that makes you feel really happy or excited?
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Why this works
Focuses on positive emotions and helps you understand what brings them joy and motivation.
13What's the most interesting thing about your family?
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What's the most interesting thing about your family?
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Why this works
Allows them to share family dynamics in a positive way while being respectful of different family structures.
14If you could create a new school club, what would it be and why?
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If you could create a new school club, what would it be and why?
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Why this works
Encourages creativity and leadership thinking while revealing their interests and organizational ideas.
15What's something you're looking forward to in the next few months?
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What's something you're looking forward to in the next few months?
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Why this works
Helps them focus on future goals and excitement while revealing their priorities and aspirations.
16What's the best advice someone has ever given you?
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What's the best advice someone has ever given you?
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Why this works
Encourages reflection on wisdom they've received while revealing what guidance has been meaningful to them.
17If 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
Develops empathy and global thinking while revealing their values and concerns about the world around them.
18What's something you're working on getting better at?
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What's something you're working on getting better at?
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Why this works
Shows growth mindset and self-awareness while encouraging them to share personal development goals.
19What's your favorite way to spend time with friends?
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What's your favorite way to spend time with friends?
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Why this works
Reveals social preferences and activities while showing interest in their friendships and social life.
20If you could give advice to someone starting middle school, what would you tell them?
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If you could give advice to someone starting middle school, what would you tell them?
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Why this works
Encourages reflection on their own experience while allowing them to share wisdom and help others.
Connecting with Middle Schoolers
Expert tips and techniques for getting the most out of these questions.
Best Practices
Keep It Age-Appropriate
Use language and topics that match their developmental stage. Avoid overly complex concepts while still challenging their thinking.
Show Genuine Interest
Listen actively and ask follow-up questions. Middle schoolers can tell when adults aren't really paying attention.
Be Patient with Responses
Give them time to think and don't rush their answers. Some kids need more processing time than others.
Question Sequences
The Interest Explorer
The Friendship Builder
Common Pitfalls
Don't Be Too Personal Too Fast
Avoid asking about family problems, relationships, or sensitive topics until you've built trust and rapport.
Don't Compare to Others
Avoid questions that might make them feel judged or compared to siblings, friends, or classmates.
Don't Rush the Conversation
Let the conversation flow naturally. Don't fire off questions like an interview - make it feel like a genuine chat.