20 Questions

Questions to Ask in Talking Stage

Meaningful questions to ask during the talking stage of dating to get to know someone better, build connection, and determine compatibility.

1

What's something you're really passionate about?

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Why this works

Reveals their interests and what drives them, helping you understand what they find meaningful and exciting.

2

What's the best part of your day?

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Why this works

Shows what brings them joy and helps you understand their daily life and what they value.

3

What's something you're really proud of?

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Why this works

Builds connection by celebrating their achievements and helps you understand what they value about themselves.

4

What's something you're looking forward to?

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Why this works

Shows their hopes and dreams while helping you understand what excites them about the future.

5

What's something you're curious about?

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Why this works

Encourages their curiosity and helps you understand their interests and what they want to learn.

6

What's something you're grateful for?

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Why this works

Encourages gratitude and helps you understand what they value and appreciate in their life.

7

What's something you're really good at that you enjoy?

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Why this works

Helps you understand their strengths and interests while building their confidence.

8

What's something that made you laugh recently?

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Why this works

Encourages sharing of positive moments and helps you understand their sense of humor.

9

What's something you're really excited about?

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Why this works

Shows their enthusiasm and helps you understand what brings them joy and anticipation.

10

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

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Why this works

Shows their hopes and dreams while helping you understand what excites them about life.

11

What's something you're curious about that you haven't explored yet?

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Why this works

Encourages their curiosity and can help you support them in trying new things.

12

What's something you wish you could do better?

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Why this works

Shows their self-awareness and helps you understand their goals and areas for growth.

13

What's something you're really good at that you enjoy?

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Why this works

Helps you understand their strengths and interests while building their confidence.

14

What's something that made you feel proud of yourself?

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Why this works

Builds self-esteem and helps you understand their accomplishments and what they value about themselves.

15

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

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Why this works

Shows their hopes and dreams while helping you understand what excites them about life.

16

What's something you're curious about that you haven't explored yet?

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Why this works

Encourages their curiosity and can help you support them in trying new things.

17

What's something you wish you could do better?

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Why this works

Shows their self-awareness and helps you understand their goals and areas for growth.

18

What's something you're really good at that you enjoy?

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Why this works

Helps you understand their strengths and interests while building their confidence.

19

What's something that made you feel proud of yourself?

Click to see why this works

Why this works

Builds self-esteem and helps you understand their accomplishments and what they value about themselves.

20

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

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Why this works

Shows their hopes and dreams while helping you understand what excites them about life.

Building Connection in the Talking Stage

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

Creating Meaningful Conversations

Be Genuinely Interested

Show authentic interest in their responses and ask follow-up questions that demonstrate you're listening.

Share Your Own Experiences

When appropriate, share your own related experiences to create connection and show vulnerability.

Keep It Light and Fun

Focus on positive, engaging topics that help you both enjoy the conversation and get to know each other.

Natural Conversation Flow

The Interest Explorer

Ask about their hobbies and passions
Explore what they're curious about
Discuss their goals and aspirations
Share your own related interests

The Daily Life

Ask about their typical day
Explore what brings them joy
Discuss their routines and habits
Share your own daily experiences

The Future Vision

Ask about their hopes and dreams
Explore what they're excited about
Discuss their goals and aspirations
Share your own future plans

Common Pitfalls to Avoid

Don't Interrogate

Avoid rapid-fire questions that feel like an interrogation. Space out questions and let the conversation flow naturally.

Avoid Heavy Topics Too Early

Keep the conversation light and positive. Save serious topics for when you've built more connection.

Don't Make It All About You

Balance sharing about yourself with asking about them. Show genuine interest in their responses.

Further Reading

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

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