Questions to Ask About Middle School
Thoughtful questions to ask about middle school experiences that help you understand someone's formative years, create deeper connections, and reveal their personal growth journey.
1What was your favorite subject in middle school, and why did you enjoy it so much?
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What was your favorite subject in middle school, and why did you enjoy it so much?
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Why this works
Reveals their academic interests and learning preferences while showing what subjects they found most engaging and meaningful.
2What was the most challenging thing about middle school for you, and how did you handle it?
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What was the most challenging thing about middle school for you, and how did you handle it?
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Why this works
Shows their resilience and problem-solving skills while revealing what they found difficult and how they coped with challenges.
3What was your favorite memory from middle school, and what made it special?
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What was your favorite memory from middle school, and what made it special?
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Why this works
Brings up positive memories while revealing what experiences they cherished and what made them meaningful.
4What was the most embarrassing thing that happened to you in middle school?
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What was the most embarrassing thing that happened to you in middle school?
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Why this works
Creates vulnerability and humor while revealing their ability to laugh at themselves and share awkward moments.
5What was your relationship with your teachers like, and which teacher had the biggest impact on you?
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What was your relationship with your teachers like, and which teacher had the biggest impact on you?
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Why this works
Shows their relationships with authority figures while revealing which teachers influenced them and how they interacted with educators.
6What was your social life like in middle school, and how did you navigate friendships and peer relationships?
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What was your social life like in middle school, and how did you navigate friendships and peer relationships?
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Why this works
Reveals their social development while showing how they handled friendships, peer pressure, and social dynamics.
7What was the most important lesson you learned in middle school that still applies to your life today?
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What was the most important lesson you learned in middle school that still applies to your life today?
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Why this works
Shows their ability to learn and grow while revealing what lessons they found most valuable and how they've applied them.
8What was your biggest fear or worry in middle school, and how did you overcome it?
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What was your biggest fear or worry in middle school, and how did you overcome it?
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Why this works
Reveals their fears and anxieties while showing how they faced and overcame their biggest concerns.
9What was your favorite extracurricular activity or club, and what did you enjoy about it?
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What was your favorite extracurricular activity or club, and what did you enjoy about it?
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Why this works
Shows their interests and involvement while revealing what activities they enjoyed and what they got out of them.
10What was the most difficult decision you had to make in middle school, and how did you make it?
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What was the most difficult decision you had to make in middle school, and how did you make it?
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Why this works
Reveals their decision-making skills while showing how they handled difficult choices and what factors influenced them.
11What was your relationship with your parents like during middle school, and how did it change?
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What was your relationship with your parents like during middle school, and how did it change?
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Why this works
Shows their family dynamics while revealing how their relationship with their parents evolved during this transitional period.
12What was the most fun thing you did with your friends in middle school?
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What was the most fun thing you did with your friends in middle school?
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Why this works
Brings up positive social memories while revealing what activities they enjoyed with friends and what made them fun.
13What was the most important goal you had in middle school, and did you achieve it?
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What was the most important goal you had in middle school, and did you achieve it?
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Why this works
Shows their goal-setting and achievement while revealing what they were working toward and whether they succeeded.
14What was the most difficult subject for you in middle school, and how did you handle it?
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What was the most difficult subject for you in middle school, and how did you handle it?
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Why this works
Reveals their academic challenges while showing how they dealt with subjects they found difficult and what strategies they used.
15What was your biggest accomplishment in middle school, and why was it important to you?
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What was your biggest accomplishment in middle school, and why was it important to you?
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Why this works
Shows their achievements while revealing what they were proud of and what made it meaningful to them.
16What was the most important advice someone gave you in middle school, and how did it help you?
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What was the most important advice someone gave you in middle school, and how did it help you?
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Why this works
Reveals their openness to guidance while showing what advice they found most valuable and how it influenced them.
17What was your relationship with your siblings like during middle school, and how did it change?
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What was your relationship with your siblings like during middle school, and how did it change?
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Why this works
Shows their family relationships while revealing how their relationship with siblings evolved during this period.
18What was the most important thing you learned about yourself in middle school?
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What was the most important thing you learned about yourself in middle school?
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Why this works
Reveals their self-discovery while showing what they learned about their own identity, strengths, and characteristics.
19What was your biggest regret from middle school, and what would you do differently?
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What was your biggest regret from middle school, and what would you do differently?
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Why this works
Shows their self-reflection while revealing what they wish they had done differently and how they've learned from it.
20What was the most important thing that happened to you in middle school that shaped who you are today?
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What was the most important thing that happened to you in middle school that shaped who you are today?
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Why this works
Reveals their formative experiences while showing what events or experiences had the biggest impact on their development.
Mastering Middle School Conversation
Expert tips and techniques for getting the most out of these questions.
Best Practices
Show Empathy for the Challenges
Approach the conversation with understanding of how difficult middle school can be. Show empathy for the challenges they faced.
Focus on Growth and Learning
Ask about lessons learned, personal growth, and how their experiences shaped them into who they are today.
Share Your Own Experiences
Reciprocate by sharing your own middle school experiences to create mutual vulnerability and deeper connection.
Question Sequences
The Academic Explorer
The Social Focus
Common Pitfalls
Don't Minimize Their Experiences
Avoid dismissing their middle school experiences as trivial. What was important to them then matters for understanding who they are now.
Don't Focus Only on the Negative
Ask about positive experiences, achievements, and good memories to balance the conversation and show interest in their successes.
Don't Rush the Conversation
Take time to listen and respond thoughtfully. Middle school experiences can be emotional and deserve careful attention.