20 Questions

Questions to Ask When Speed Dating

Make the most of your speed dating experience with these engaging questions that help you quickly assess compatibility, create connection, and determine if you want to see someone again.

1

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

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Why this works

Quick way to learn about their lifestyle and interests while revealing what they consider exciting or noteworthy in their life.

2

If you could have dinner with anyone, who would it be?

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Why this works

Reveals their values, interests, and intellectual curiosity while being universally engaging and easy to answer quickly.

3

What's something you're passionate about?

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Why this works

Shows what drives them and what they care about most, helping you understand their priorities and energy.

4

What's the best part of your day?

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Why this works

Reveals their daily life and what brings them joy, helping you understand their lifestyle and happiness sources.

5

If you could travel anywhere right now, where would you go?

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Why this works

Shows their sense of adventure and interests while being a fun, easy question that reveals their travel preferences and dreams.

6

What's something that always makes you laugh?

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Why this works

Reveals their sense of humor and what they find funny, which is crucial for compatibility and connection.

7

What's your ideal way to spend a weekend?

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Why this works

Shows their lifestyle preferences and how they like to relax or have fun, helping you understand their energy and interests.

8

What's something you're looking forward to?

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Why this works

Reveals their future plans and what excites them, showing their optimism and forward-thinking nature.

9

What's the most random thing you know?

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Why this works

Fun way to learn about their knowledge and interests while showing their personality and what they find interesting.

10

What's something you're proud of?

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Why this works

Reveals their achievements and values while showing what they consider important and worth celebrating.

11

If you could learn any skill instantly, what would it be?

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Why this works

Shows their interests and aspirations while revealing what they value and what they'd like to accomplish.

12

What's your favorite way to unwind?

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Why this works

Reveals their relaxation preferences and how they handle stress, helping you understand their lifestyle and needs.

13

What's something that always puts you in a good mood?

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Why this works

Shows what makes them happy and what they value, helping you understand their sources of joy and positivity.

14

If you could have any superpower, what would it be?

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Why this works

Fun, creative question that reveals their personality and what they value most in life.

15

What's the most interesting place you've been?

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Why this works

Shows their travel experiences and interests while revealing what they consider fascinating or memorable.

16

What's something you're curious about?

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Why this works

Reveals their intellectual interests and what they want to learn, showing their curiosity and growth mindset.

17

What's your favorite way to celebrate?

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Why this works

Shows their personality and how they like to have fun, revealing their social preferences and energy.

18

What's something that always surprises you?

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Why this works

Reveals their perspective on life and what they find unexpected or interesting, showing their worldview and curiosity.

19

What's the best advice you've ever received?

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Why this works

Shows their values and what they consider important while revealing their wisdom and life experience.

20

What's something you're grateful for today?

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Why this works

Reveals their appreciation and positivity while showing what they value and what brings them joy.

Best Practices for Speed Dating

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

Best Practices

Keep Questions Light and Fun

Focus on questions that are easy to answer quickly and reveal personality without being too personal or intense for a short conversation.

Listen and Respond Genuinely

Show genuine interest in their answers and ask follow-up questions. This creates connection and shows you're engaged with what they're saying.

Be Yourself and Have Fun

Don't try to be someone you're not. Be authentic and enjoy the experience. Speed dating should be fun and low-pressure.

Question Sequences

The Interest and Lifestyle Sequence

1
What's the most interesting thing you've done recently?
2
What's something you're passionate about?
3
What's your ideal way to spend a weekend?

The Fun and Personality Sequence

1
What's something that always makes you laugh?
2
If you could have any superpower, what would it be?
3
What's the most random thing you know?

Common Pitfalls

Don't Ask Personal or Intense Questions

Avoid questions about past relationships, family problems, or deep personal issues. Keep it light and fun for the short time you have.

Don't Try to Impress Too Much

Be yourself and focus on connection rather than trying to impress them with your accomplishments or knowledge.

Don't Ignore Their Answers

Listen to what they're saying and respond genuinely. Don't just wait for your turn to talk or ask the next question.

Conversation Templates

The Interest and Lifestyle Focus

1
Step 1: Start with: "What's the most interesting thing you've done recently?"
2
Step 2: Explore with: "What's something you're passionate about?"
3
Step 3: Conclude with: "What's your ideal way to spend a weekend?"

The Fun and Personality Focus

1
Step 1: Begin with: "What's something that always makes you laugh?"
2
Step 2: Follow with: "If you could have any superpower, what would it be?"
3
Step 3: Deepen with: "What's the most random thing you know?"

Further Reading

"The Art of Conversation" by Catherine Blyth
"How to Talk to Anyone" by Leil Lowndes
"The Charisma Myth" by Olivia Fox Cabane

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