20 Questions

Questions to Ask Your Older Sister

Meaningful questions to ask your older sister that strengthen your bond, learn from her experiences, and create deeper understanding between siblings.

1

What's something you wish you had known when you were my age?

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Why this works

Reveals her wisdom and life lessons while providing valuable guidance for your own journey and decisions.

2

What's your favorite memory of us growing up together?

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Why this works

Strengthens your bond by focusing on positive shared experiences and helps you both appreciate your relationship.

3

What's something you're proud of that you want me to know about?

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Why this works

Celebrates her achievements while showing support and pride in her accomplishments and personal growth.

4

What's something you've learned about yourself that you wish you had known earlier?

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Why this works

Shows her self-awareness and provides valuable insights that can help you understand yourself better.

5

What's your advice for handling the challenges I'm facing right now?

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Why this works

Provides practical guidance while showing her care and support for your current situation and struggles.

6

What's something you're excited about in your life right now?

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Why this works

Shows interest in her current life while creating opportunities for shared joy and celebration.

7

What's something you're worried about that you'd like to talk about?

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Why this works

Creates a safe space for her to share concerns while showing your support and care for her well-being.

8

What's your favorite way to spend time together, and what would you like to do more of?

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Why this works

Reveals her preferences for quality time while helping you plan meaningful activities together.

9

What's something you've changed your mind about over the years?

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Why this works

Shows her growth and evolution while providing valuable lessons about being open to new perspectives.

10

What's your favorite thing about our relationship?

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Why this works

Strengthens your bond by focusing on what you both value most about your sibling relationship.

11

What's something you wish you could tell our younger selves?

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Why this works

Reveals her perspective on your shared childhood while providing wisdom for both of you.

12

What's something you're grateful for that you want me to know about?

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Why this works

Shows her appreciation and helps you understand what she values most in her life.

13

What's your advice for maintaining a strong sibling relationship?

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Why this works

Provides practical guidance for strengthening your bond while showing her commitment to your relationship.

14

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

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Why this works

Shows her optimism and forward-thinking while creating opportunities for shared excitement and planning.

15

What's something you've learned from our parents that you want to pass on to me?

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Why this works

Reveals family wisdom and helps you understand the values and lessons she's gained from your shared upbringing.

16

What's your favorite way to show love and support to family?

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Why this works

Reveals her love language and helps you understand how to show your care and support for her.

17

What's something you're proud of me for that I might not know?

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Why this works

Provides positive reinforcement while showing her pride and support for your accomplishments.

18

What's your advice for handling family dynamics and relationships?

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Why this works

Provides practical guidance for navigating family situations while showing her wisdom and experience.

19

What's something you're excited to share with me or teach me?

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Why this works

Creates opportunities for learning and connection while showing her desire to share knowledge and experiences.

20

What's your vision for our relationship in the future?

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Why this works

Creates shared goals and helps you both work toward strengthening your bond and relationship.

Best Practices for Sibling Conversations

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

Best Practices

Show Genuine Interest and Respect

Demonstrate that you value her experiences and wisdom while showing respect for her perspective and life journey.

Listen Actively and Show Empathy

Pay attention to her responses and show understanding for her experiences, even when you don't fully relate.

Be Open to Learning and Growing

Approach conversations with humility and a genuine desire to learn from her experiences and wisdom.

Conversation Starters

The Wisdom Exchange

1
What's something you wish you had known when you were my age?
2
What's your advice for handling the challenges I'm facing right now?
3
What's something you've learned about yourself that you wish you had known earlier?
4
What's your advice for maintaining a strong sibling relationship?

The Bond Strengthener

1
What's your favorite memory of us growing up together?
2
What's your favorite thing about our relationship?
3
What's your favorite way to spend time together?
4
What's your vision for our relationship in the future?

Common Pitfalls

Don't Compare or Compete

Avoid questions that pit you against each other or create unnecessary competition. Focus on mutual support and understanding.

Avoid Bringing Up Old Wounds

Don't ask questions that might trigger painful memories or create tension. Focus on positive and constructive topics.

Don't Minimize Her Experiences

Show respect for her life journey and experiences, even if they're different from your own.

Conversation Templates

The Wisdom Seeker

1
Step 1: Start with: "What's something you wish you had known when you were my age?"
2
Step 2: Follow with: "What's your advice for handling the challenges I'm facing right now?"
3
Step 3: Explore with: "What's something you've learned about yourself that you wish you had known earlier?"

The Bond Builder

1
Step 1: Begin with: "What's your favorite memory of us growing up together?"
2
Step 2: Connect with: "What's your favorite thing about our relationship?"
3
Step 3: Plan with: "What's your vision for our relationship in the future?"

Further Reading

"Siblings Without Rivalry" by Adele Faber and Elaine Mazlish
"The Sibling Effect" by Jeffrey Kluger
"Adult Sibling Relationships" by Geoffrey Greif

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