20 Questions

Questions to Ask on Speed Dating

Quick, engaging questions perfect for speed dating that help you make a genuine connection in a short amount of time while revealing personality and compatibility.

1

What's the most interesting thing you've done this week?

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Why this works

Opens up conversation about their recent activities and reveals what they find interesting or exciting in their daily life.

2

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

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Why this works

Reveals their interests, values, and what they find inspiring while being a universally engaging question that's easy to answer.

3

What's something you're really passionate about?

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Why this works

Shows what drives them and reveals their interests and values, helping you understand what they care about most.

4

What's the best adventure you've ever been on?

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Why this works

Reveals their sense of adventure and what they find exciting, while often leading to interesting stories about their experiences.

5

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

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Why this works

Shows their travel interests and reveals what they find appealing about different places and cultures.

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 amusing, helping you understand their personality and what makes them happy.

7

What's the most spontaneous thing you've ever done?

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Why this works

Shows their adventurousness and reveals their approach to life, often leading to interesting stories about their experiences.

8

What's something you're really good at that you're proud of?

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Why this works

Reveals their skills and achievements while showing what they value and what they're proud of in their life.

9

What's your favorite way to spend a weekend?

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Why this works

Shows their lifestyle preferences and reveals what they find relaxing or enjoyable in their free time.

10

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

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Why this works

Reveals their interests and aspirations while showing what they find appealing about different skills and activities.

11

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

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Why this works

Shows what makes them happy and reveals their approach to maintaining a positive outlook on life.

12

What's the most interesting place you've ever visited?

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Why this works

Reveals their travel experiences and what they find appealing about different places, often leading to interesting stories.

13

What's something you're really looking forward to?

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Why this works

Shows their hopes and dreams while revealing what they find exciting about their future plans.

14

What's your favorite way to meet new people?

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Why this works

Reveals their social preferences and approach to meeting people, helping you understand their social style.

15

What's something that always makes you smile?

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Why this works

Shows what brings them joy and reveals their personality and what they find uplifting in life.

16

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

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Why this works

Reveals their curiosity and interests while showing what they find engaging and worth learning about.

17

What's your favorite way to relax after a busy day?

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Why this works

Shows their approach to self-care and reveals what they find relaxing and rejuvenating.

18

What's something you're really curious about?

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Why this works

Reveals their interests and what they find intriguing, helping you understand their intellectual curiosity.

19

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

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Why this works

Shows their values and what they find meaningful while revealing what advice has impacted them most.

20

What's something that always makes you feel grateful?

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Why this works

Reveals their values and what they appreciate in life, showing their approach to gratitude and positivity.

Best Practices for Speed Dating Conversations

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

Best Practices

Keep Questions Light and Engaging

Speed dating is about making a quick connection, so focus on questions that are easy to answer and reveal personality without being too personal or intense.

Show Genuine Interest in Their Responses

Listen actively to their answers and ask follow-up questions that show you're interested in what they're saying. This creates a more engaging conversation.

Be Yourself and Stay Positive

Be authentic and maintain a positive attitude. Speed dating is about finding compatibility, so let your true personality shine through.

Question Sequences

The Interest and Passion Sequence

1
What's something you're really passionate about?
2
What's the most interesting thing you've learned recently?
3
What's something you're really curious about?

The Adventure and Experience Flow

1
What's the best adventure you've ever been on?
2
What's the most interesting place you've ever visited?
3
What's the most spontaneous thing you've ever done?

Common Pitfalls

Don't Ask Overly Personal Questions

Avoid questions about past relationships, family problems, or deeply personal topics. Keep the conversation light and appropriate for a first meeting.

Avoid Controversial or Sensitive Topics

Don't bring up politics, religion, or other potentially divisive topics. Focus on neutral, engaging topics that help you get to know each other.

Don't Dominate the Conversation

Make sure to listen as much as you talk. Speed dating is about mutual connection, so give them space to share and ask questions too.

Conversation Templates

The Interest and Passion Flow

1
Step 1: Start with: "What's something you're really passionate about?"
2
Step 2: Continue with: "What's the most interesting thing you've learned recently?"
3
Step 3: Finish with: "What's something you're really curious about?"

The Adventure and Experience Sequence

1
Step 1: Begin with: "What's the best adventure you've ever been on?"
2
Step 2: Follow with: "What's the most interesting place you've ever visited?"
3
Step 3: End with: "What's the most spontaneous thing you've ever done?"

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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