20 Questions

Questions to Ask About Hobbies

Connect with others through thoughtful questions about their hobbies and interests that reveal their passions, skills, and personality while building meaningful relationships around shared interests.

1

What's your favorite hobby and why do you enjoy it?

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Why this works

Opens up their passion while revealing what they find most enjoyable and fulfilling about their hobby.

2

How did you get started with this hobby?

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Why this works

Reveals their journey while showing how they discovered and began their hobby, which often reveals their personality and interests.

3

What's the most challenging aspect of this hobby for you?

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Why this works

Shows their growth mindset while revealing what they find most difficult and how they approach challenges.

4

What's your approach to learning and improving in this hobby?

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Why this works

Demonstrates their learning style while revealing how they develop skills and knowledge in their hobby.

5

What's the most rewarding aspect of this hobby for you?

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Why this works

Focuses on positive aspects while revealing what they find most fulfilling and satisfying about their hobby.

6

How do you balance this hobby with other commitments and responsibilities?

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Why this works

Shows their time management while revealing how they prioritize and manage their hobby alongside other life demands.

7

What's your approach to working with different types of equipment and tools?

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Why this works

Demonstrates their technical skills while revealing how they work with various tools and equipment in their hobby.

8

How do you handle the pressure and expectations that come with this hobby?

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Why this works

Shows their resilience while revealing how they manage stress and expectations in their hobby.

9

What's your approach to working with different types of people and communities?

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Why this works

Demonstrates their social skills while revealing how they interact with others who share their hobby.

10

What's your approach to working with different types of projects and challenges?

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Why this works

Shows their problem-solving while revealing how they approach various projects and challenges in their hobby.

11

How do you handle the responsibility of maintaining and caring for your hobby equipment?

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Why this works

Demonstrates their responsibility while revealing how they maintain and care for their hobby-related equipment and materials.

12

What's your approach to working with different types of feedback and criticism?

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Why this works

Shows their openness while revealing how they receive and process feedback from others in their hobby community.

13

What's your approach to working with different types of goals and objectives?

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Why this works

Demonstrates their goal-setting while revealing how they set and work toward goals in their hobby.

14

How do you handle the challenge of staying motivated and engaged in this hobby?

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Why this works

Shows their motivation while revealing how they maintain interest and engagement in their hobby over time.

15

What's your approach to working with different types of resources and materials?

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Why this works

Demonstrates their resourcefulness while revealing how they work with various materials and resources in their hobby.

16

What's your approach to working with different types of techniques and methods?

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Why this works

Shows their adaptability while revealing how they learn and apply various techniques and methods in their hobby.

17

How do you handle the responsibility of sharing your hobby with others?

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Why this works

Demonstrates their teaching skills while revealing how they share their hobby knowledge and experience with others.

18

What's your approach to working with different types of competition and performance?

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Why this works

Shows their competitive spirit while revealing how they approach competition and performance in their hobby.

19

What's the most important thing you've learned from this hobby?

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Why this works

Focuses on learning outcomes while revealing what they consider most valuable from their hobby experience.

20

What's your vision for this hobby and how do you plan to develop it further?

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Why this works

Shows their future thinking while revealing their goals and plans for continuing and developing their hobby.

Connecting Through Hobbies

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

Best Practices

Show Genuine Interest

Ask questions that demonstrate you're genuinely interested in their hobby and passion. This creates connection and shows you value their interests.

Respect Their Knowledge

Recognize that hobby enthusiasts often have deep knowledge and experience. Ask questions that show respect for their expertise and passion.

Focus on Their Experiences

Ask about their personal experiences with their hobby, projects, and community. This reveals their unique perspective and creates meaningful conversation.

Question Sequences

The Passion Explorer

1
What's your favorite hobby and why do you enjoy it?
2
How did you get started with this hobby?
3
What's the most rewarding aspect of this hobby for you?

The Learning Focus

1
What's the most challenging aspect of this hobby for you?
2
What's your approach to learning and improving in this hobby?
3
What's the most important thing you've learned from this hobby?

Common Pitfalls

Don't Make Assumptions About Their Skill Level

Don't assume you know their level of expertise or experience. Ask questions that allow them to share their knowledge and experience.

Avoid Generic Questions

Don't ask questions you could easily find on the internet. Ask about their personal experiences and unique perspective.

Don't Focus Only on the Positive

While hobbies are enjoyable, also ask about challenges and difficulties. These experiences often provide the most valuable insights.

Conversation Templates

The Passion Explorer

1
Step 1: Start with: "What's your favorite hobby and why do you enjoy it?"
2
Step 2: Follow with: "How did you get started with this hobby?"
3
Step 3: Deepen with: "What's the most rewarding aspect of this hobby for you?"

The Learning Focus

1
Step 1: Begin with: "What's the most challenging aspect of this hobby for you?"
2
Step 2: Explore with: "What's your approach to learning and improving in this hobby?"
3
Step 3: Connect with: "What's the most important thing you've learned from this hobby?"

Further Reading

"The Art of Learning" by Josh Waitzkin
"Flow" by Mihaly Csikszentmihalyi
"The Power of Passion" by Terri Trespicio

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