20 Questions

Deep Questions to Ask Teens

Thought-provoking questions that help you connect with teenagers on a deeper level while understanding their perspectives, values, and aspirations during this important developmental stage.

1

What are your biggest dreams and what do you hope to achieve in life?

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Why this works

Opens conversation on aspirations and reveals their goals, dreams, and what they hope to accomplish in their future.

2

What are your biggest fears and what worries you most about the future?

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Why this works

Creates vulnerability and bonding while revealing their concerns, fears, and what they find most challenging about growing up.

3

What values are most important to you and how do you try to live by them?

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Why this works

Shows interest in their character and reveals their core values, principles, and how they try to live according to their beliefs.

4

What do you think is the most important thing you've learned so far in life?

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Why this works

Reveals their wisdom and shows what lessons and insights they've gained from their experiences and what they find most valuable.

5

What are your biggest challenges right now and how are you dealing with them?

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Why this works

Shows interest in their struggles and reveals what difficulties they're facing and how they're coping with challenges.

6

What do you think makes someone a good person and how do you try to be one?

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Why this works

Reveals their moral compass and shows what they consider important in character and how they try to be a good person.

7

What are your favorite ways to express yourself and be creative?

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Why this works

Shows interest in their self-expression and reveals what creative outlets and forms of expression they enjoy and value.

8

What do you think about the world today and what changes would you like to see?

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Why this works

Reveals their worldview and shows their thoughts on current events, social issues, and what they'd like to change about the world.

9

What are your relationships like with your friends and family?

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Why this works

Shows interest in their social connections and reveals how they navigate relationships with friends and family members.

10

What do you think about school and what are your favorite and least favorite subjects?

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Why this works

Reveals their academic interests and shows what subjects they enjoy, what they find challenging, and their thoughts on education.

11

What are your favorite ways to have fun and what do you enjoy doing in your free time?

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Why this works

Shows interest in their interests and reveals what activities and pastimes they enjoy and find fun and engaging.

12

What do you think about social media and how does it affect your life?

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Why this works

Reveals their thoughts on technology and shows how social media impacts their life, relationships, and self-image.

13

What are your thoughts on peer pressure and how do you handle it?

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Why this works

Shows interest in their social challenges and reveals how they navigate peer pressure and make decisions about fitting in.

14

What do you think about the future and what are you most excited or nervous about?

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Why this works

Reveals their hopes and concerns and shows what they're looking forward to and what they find most challenging about the future.

15

What are your favorite ways to learn and what subjects or topics interest you most?

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Why this works

Shows interest in their learning and reveals what subjects, topics, or learning methods they find most engaging and effective.

16

What do you think about money and what are your thoughts on financial responsibility?

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Why this works

Reveals their financial awareness and shows their thoughts on money, spending, saving, and financial responsibility.

17

What are your thoughts on relationships and what do you look for in friends or romantic partners?

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Why this works

Shows interest in their social connections and reveals their thoughts on relationships, friendship, and what they value in others.

18

What do you think about your generation and what makes you unique?

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Why this works

Reveals their generational identity and shows their thoughts on their generation and what they think makes them unique.

19

What are your thoughts on mental health and how do you take care of your emotional well-being?

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Why this works

Shows interest in their well-being and reveals their thoughts on mental health and how they care for their emotional health.

20

What do you think about the world you're inheriting and what kind of world do you want to create?

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Why this works

Reveals their vision for the future and shows their thoughts on the world they're inheriting and what kind of world they want to create.

Best Practices for Teen Conversations

Expert tips and techniques for getting the most out of these questions.

Best Practices

Show Genuine Interest in Their Perspectives

Demonstrate authentic curiosity about their thoughts, feelings, and experiences. Ask follow-up questions and show enthusiasm for their insights and ideas.

Be Patient and Non-Judgmental

Give them time to share their thoughts and experiences. Be supportive and non-judgmental when they share personal information or concerns.

Respect Their Boundaries and Privacy

Respect when they don't want to share something. Don't pressure them to reveal information they're not comfortable sharing.

Question Sequences

The Dreams and Aspirations Sequence

1
What are your biggest dreams and what do you hope to achieve in life?
2
What are your biggest fears and what worries you most about the future?
3
What do you think about the future and what are you most excited or nervous about?
4
What do you think about the world you're inheriting and what kind of world do you want to create?

The Values and Character Sequence

1
What values are most important to you and how do you try to live by them?
2
What do you think makes someone a good person and how do you try to be one?
3
What are your thoughts on relationships and what do you look for in friends or romantic partners?
4
What are your thoughts on mental health and how do you take care of your emotional well-being?

Common Pitfalls

Don't Judge or Criticize Their Choices

Avoid judging them for their thoughts, feelings, or experiences. Create a supportive environment where they feel accepted and understood.

Don't Pressure Them to Share

Respect when they don't want to answer a question. Don't pressure them to reveal information they're not comfortable sharing.

Don't Ignore Their Individuality

Acknowledge their unique perspectives and experiences. Show appreciation for their individuality and what makes them special.

Conversation Templates

The Dreams and Aspirations Approach

1
Step 1: Start with: "I want to understand your hopes and dreams..."
2
Step 2: Ask: "What are your biggest dreams and what do you hope to achieve in life?"
3
Step 3: Explore: "What are your biggest fears and what worries you most about the future?"
4
Step 4: Connect: "What do you think about the future and what are you most excited or nervous about?"

The Values and Character Approach

1
Step 1: Begin with: "I'm interested in understanding your values and character..."
2
Step 2: Ask: "What values are most important to you and how do you try to live by them?"
3
Step 3: Explore: "What do you think makes someone a good person and how do you try to be one?"
4
Step 4: Connect: "What are your thoughts on relationships and what do you look for in friends or romantic partners?"

Further Reading

"The Art of Conversation" by Catherine Blyth
"How to Win Friends and Influence People" by Dale Carnegie
"The Friendship Factor" by Alan Loy McGinnis
"The Art of Friendship" by William Rawlins

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