20 Questions

Questions to Ask in Speed Dating

Maximize your speed dating experience with strategic questions that quickly reveal compatibility, personality, and potential while making the most of limited time.

1

What's the most interesting thing you've done recently?

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Why this works

Opens up their current life while revealing their interests, activities, and what they find exciting or engaging.

2

What's your ideal way to spend a weekend?

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Why this works

Reveals their lifestyle preferences while showing what activities and environments they find most enjoyable and relaxing.

3

What's something you're passionate about that most people don't know?

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Why this works

Opens up their hidden interests while revealing what they care deeply about but may not share openly.

4

What's the best trip you've ever taken?

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Why this works

Reveals their travel interests while showing what experiences they value and what kind of adventures they enjoy.

5

What's something you're looking forward to in the near future?

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Why this works

Shows their hopes and plans while revealing what they're excited about and what motivates them.

6

What's your favorite way to have fun?

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Why this works

Reveals their idea of enjoyment while showing what activities and experiences they find most entertaining and fulfilling.

7

What's something you've learned about yourself recently?

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Why this works

Demonstrates their self-awareness while revealing their ongoing personal development and growth.

8

What's your ideal date night?

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Why this works

Shows their relationship preferences while revealing what kind of experiences they value in romantic relationships.

9

What's something you're grateful for that others might not notice?

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Why this works

Opens up their appreciation while revealing what they value and notice that others might overlook.

10

What's your favorite way to relax and unwind?

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Why this works

Reveals their stress management while showing what activities and environments they find most restorative.

11

What's something you're curious about or want to learn more about?

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Why this works

Reveals their intellectual curiosity while showing what topics and ideas they find most interesting and worth exploring.

12

What's your favorite way to spend time with friends?

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Why this works

Shows their social preferences while revealing what kind of social activities and interactions they enjoy most.

13

What's something you're proud of that you accomplished recently?

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Why this works

Opens up their achievements while revealing what they value and what they consider worth celebrating.

14

What's your favorite way to learn or explore new things?

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Why this works

Shows their learning style while revealing how they prefer to acquire knowledge and explore new experiences.

15

What's something you find beautiful or inspiring that others might not notice?

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Why this works

Opens up their aesthetic sense while revealing what they find meaningful and beautiful in the world.

16

What's your favorite way to handle stress or difficult situations?

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Why this works

Shows their coping strategies while revealing how they manage challenges and maintain their well-being.

17

What's something you're excited about that's coming up?

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Why this works

Reveals their enthusiasm while showing what events, experiences, or opportunities they're most looking forward to.

18

What's your favorite way to connect with people?

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Why this works

Shows their communication style while revealing how they prefer to build relationships and connect with others.

19

What's something you've discovered recently that you love?

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Why this works

Reveals their openness to new experiences while showing what they've recently found enjoyable or valuable.

20

What's the most important thing for someone to know about you?

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Why this works

Gives them a chance to share what they consider most important while revealing what they want others to understand about them.

Mastering Speed Dating Conversations

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

Best Practices

Keep Questions Light and Positive

Focus on questions that reveal personality and interests without getting too deep or personal. Save heavy topics for later dates.

Listen Actively

Give them your full attention and show genuine interest in their responses. This creates connection and shows you value what they have to say.

Be Authentic

Be yourself and ask questions you're genuinely curious about. Authenticity creates better connections than trying to impress.

Question Sequences

The Interest Explorer

1
What's the most interesting thing you've done recently?
2
What's something you're passionate about that most people don't know?
3
What's something you're curious about or want to learn more about?

The Lifestyle Focus

1
What's your ideal way to spend a weekend?
2
What's your favorite way to have fun?
3
What's your favorite way to relax and unwind?

Common Pitfalls

Don't Ask About Exes

Avoid questions about past relationships or ex-partners. This is too personal for speed dating and can create awkwardness.

Avoid Controversial Topics

Don't ask about politics, religion, or other controversial topics. These can create tension and aren't appropriate for speed dating.

Don't Make It an Interview

Don't rapid-fire questions without engaging with their answers. Have a conversation, not an interrogation.

Conversation Templates

The Interest Explorer

1
Step 1: Start with: "What's the most interesting thing you've done recently?"
2
Step 2: Follow with: "What's something you're passionate about that most people don't know?"
3
Step 3: Deepen with: "What's something you're curious about or want to learn more about?"

The Lifestyle Focus

1
Step 1: Begin with: "What's your ideal way to spend a weekend?"
2
Step 2: Explore with: "What's your favorite way to have fun?"
3
Step 3: Connect with: "What's your favorite way to relax and unwind?"

Further Reading

"The Art of Conversation" by Catherine Blyth
"How to Win Friends and Influence People" by Dale Carnegie
"The Charisma Myth" by Olivia Fox Cabane

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