20 Questions

Questions to Ask Your Long Distance Boyfriend

Meaningful questions to maintain connection, deepen intimacy, and strengthen your long-distance relationship through thoughtful conversation.

1

What's something you're really excited about that happened today?

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Why this works

Helps you stay connected to his daily life and understand what brings him joy and excitement.

2

What's something you're looking forward to this week?

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Why this works

Shows his enthusiasm and helps you understand what he's anticipating and planning.

3

What's something you wish you could share with me right now?

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Why this works

Creates intimacy and helps you understand what moments he wishes you could experience together.

4

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

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Why this works

Builds connection by celebrating his achievements and helps you understand what he values about himself.

5

What's something you're struggling with that I can help support you through?

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Why this works

Creates space for him to share difficulties and helps you understand how you can support him from a distance.

6

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

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Why this works

Encourages his curiosity and helps you understand his interests and learning goals.

7

What's something you're grateful for today?

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Why this works

Encourages gratitude and helps you understand what he values and appreciates in his life.

8

What's something you wish you could tell me but haven't?

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Why this works

Creates a safe space for open communication and helps you understand what he might be holding back.

9

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

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Why this works

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

10

What's something that made you laugh recently?

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Why this works

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

11

What's something you wish you could do better?

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Why this works

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

12

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

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Why this works

Shows his hopes and dreams while helping you understand what excites him about life.

13

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

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Why this works

Encourages his curiosity and can help you support him in trying new things.

14

What's something you wish you could change about yourself?

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Why this works

Creates space for self-reflection while helping you understand his self-perception and goals.

15

What's something you love about our relationship?

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Why this works

Encourages appreciation for your bond while helping you understand what he values about your connection.

16

What's something you're really excited about that we can do together when we're together?

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Why this works

Builds anticipation for your time together and helps you plan meaningful activities.

17

What's something you wish you could tell me but haven't?

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Why this works

Creates a safe space for open communication and helps you understand what he might be holding back.

18

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

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Why this works

Shows his hopes and dreams while helping you understand what excites him about life.

19

What's something you love about being you?

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Why this works

Builds self-love and helps you understand what he values about himself and his identity.

20

What's something you wish you could tell me but haven't?

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Why this works

Creates a safe space for open communication and helps you understand what he might be holding back.

Maintaining Connection in Long-Distance Relationships

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

Creating Meaningful Conversations

Listen Without Judgment

Create a safe space where your partner feels comfortable sharing their thoughts and feelings without fear of criticism.

Ask Follow-up Questions

Show genuine interest by asking follow-up questions that help you understand their perspective better.

Share Your Own Experiences

When appropriate, share your own related experiences to create connection and show that you understand.

Natural Conversation Flow

The Daily Check-in

Ask about their day and experiences
Explore what they're excited or worried about
Discuss what they learned or discovered
End with gratitude or looking forward

The Interest Explorer

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

The Emotional Check-in

Ask about their feelings and emotions
Explore what makes them happy or worried
Discuss their relationships with others
Create space for difficult conversations

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 Leading Questions

Don't ask questions that suggest the answer you want to hear. Let them share their genuine thoughts and feelings.

Don't Dismiss Their Feelings

Even if their concerns seem small to you, they're real to them. Validate their feelings and take them seriously.

Further Reading

"The 5 Love Languages" by Gary Chapman
"Long Distance Relationships" by Gregory Guldner
"The Seven Principles for Making Marriage Work" by John Gottman

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