20 Questions

What If Questions to Ask Your Boyfriend

Fun and thought-provoking 'what if' questions to ask your boyfriend to explore his personality, values, and deepen your connection through imaginative scenarios.

1

What if you could have any superpower for one day?

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Why this works

This fun question reveals his values and priorities by showing what he would choose to do with unlimited power.

2

What if you could travel back in time to any period in history?

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Why this works

Understanding his historical interests helps you learn about his curiosity and what periods or events fascinate him.

3

What if you could have dinner with any three people, living or dead?

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Why this works

This reveals his heroes, interests, and the type of people he admires or wants to learn from.

4

What if you could live anywhere in the world for a year?

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Why this works

Understanding his travel dreams and preferences helps you learn about his sense of adventure and lifestyle preferences.

5

What if you could master any skill instantly?

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Why this works

This shows what he values most and what skills he thinks would be most beneficial or fulfilling.

6

What if you could change one thing about the world?

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Why this works

Understanding what he would change reveals his values, concerns, and what he thinks is most important in the world.

7

What if you could be famous for something?

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Why this works

This reveals what he's passionate about and what kind of impact he'd like to have on the world.

8

What if you could read minds for one day?

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Why this works

This fun question reveals his curiosity about others and what he's most interested in understanding about people.

9

What if you could have any job in the world?

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Why this works

Understanding his dream career helps you learn about his passions and what kind of work would fulfill him.

10

What if you could be invisible for a day?

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Why this works

This reveals his curiosity and what he's most interested in observing or experiencing without being seen.

11

What if you could have any animal as a pet?

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Why this works

This fun question reveals his preferences and what kind of companionship he values.

12

What if you could speak any language fluently?

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Why this works

Understanding his language interests helps you learn about his cultural interests and communication preferences.

13

What if you could have any car in the world?

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Why this works

This reveals his preferences for style, performance, and what he values in transportation and lifestyle.

14

What if you could have any house in the world?

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Why this works

Understanding his dream home helps you learn about his lifestyle preferences and what kind of environment he values.

15

What if you could have any superpower permanently?

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Why this works

This reveals what he values most and what kind of impact he'd like to have on the world long-term.

16

What if you could be any age for the rest of your life?

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Why this works

This reveals what he values about different life stages and what age he feels most comfortable with.

17

What if you could have any talent or ability?

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Why this works

Understanding his dream talents helps you learn about his passions and what he thinks would be most fulfilling.

18

What if you could have any meal for the rest of your life?

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Why this works

This fun question reveals his food preferences and what he values in dining experiences.

19

What if you could have any hobby or interest?

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Why this works

Understanding his dream hobbies helps you learn about his interests and what he finds most engaging.

20

What if you could have any experience in the world?

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Why this works

This reveals his sense of adventure and what kind of experiences he values most in life.

Using What If Questions Effectively

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

Before the Conversation

Choose the Right Time

Pick a relaxed, fun moment when you're both in a good mood and ready to be playful and imaginative.

Create a Fun Atmosphere

Make it feel like a game or fun activity rather than a serious interrogation. Keep the mood light and playful.

Be Open to Their Answers

Listen with curiosity and interest rather than judgment. These questions are about exploring and having fun together.

During the Conversation

Ask Follow-up Questions

When they give interesting answers, ask why they chose that option or what appeals to them about it.

Share Your Own Answers

Make it a two-way conversation by sharing your own answers to the same questions.

Be Playful and Curious

Keep the tone light and fun. These questions are meant to be entertaining and help you learn about each other.

What You Can Learn

Values and Priorities

Pay attention to what they choose and why. This reveals their values and what they prioritize in life.

Interests and Passions

Notice what excites them or what they're most curious about. This helps you understand their interests and passions.

Personality and Character

Observe how they think and what kind of choices they make. This reveals their personality and character traits.

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation