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50 Best Questions To Ask Your Sister Or Brother

Your brother or sister was most likely the first friend you ever had, and throughout the years you’ve probably made and shared thousands of memories together.

While you might sometimes drive each other crazy, it’s comforting to think that you have a special bond with your sibling that will hopefully last a lifetime.

If you are lucky enough to have a brother or sister and want to strengthen that relationship even further, a great option is to ask a list of awesome questions.

Knowing what to ask is sometimes easier said than done, so to help inspire you, here are 50 of the best questions to ask your sister or brother:

Good Questions To Ask Your Sibling

  1. What’s your dream job?
  2. Who is your hero?
  3. What makes you feel your most confident?
  4. What’s your best childhood memory?
  5. What’s the one thing that people never realize or know about you?
  6. If there’s one thing you could change about our childhood, what would it be?
  7. What’s the best book you’ve ever read?
  8. What is your favorite movie of all time?
  9. Is there a song that instantly makes you happy when you hear it?
  10. If you could go anywhere in a time machine, where would you go?
  11. What is your biggest regret to date?
  12. Do you think we’d be friends if we weren’t siblings?
  13. How much money would it take for you not to use your cell phone for one week / month year?
  14. What would it take for you to consider your life a success?
  15. What achievement are you most proud of?
  16. What’s the most difficult decision you’ve ever made?
  17. What’s the best decision you’ve ever made?
  18. Tell me about something you’ve done that you’ll never do again and why.
  19. If your room was on fire and you could save 3 things, what would you grab?
  20. What’s the most annoying nickname you’ve ever had?

Relationship Questions For Siblings

  1. Who was your first crush?
  2. Tell me about your first kiss.
  3. Who do you love more, mom or dad?
  4. Describe your dream wedding.
  5. What’s your best memory of the two of us?
  6. What’s the best date you’ve ever been on?
  7. What’s the worst date you’ve ever been on?
  8. Describe your dream date – what does he or she look and act like?
  9. What do you find most annoying about me?
  10. What do you find most annoying about mom or dad?

Funny Questions To Ask Your Sister Or Brother

  1. Have you ever pretended to be sick to get out of something?
  2. What’s the best prank you’ve ever played on someone?
  3. Would you rather marry for love and be poor, or for money and be happy?
  4. If you could only eat one meal for a week straight, what would you choose?
  5. Would you rather be beautiful and unhappy or ugly or happy?
  6. What’s the most embarrassing thing you’ve ever done?
  7. Would you rather be superman/woman or batman/woman?
  8. Who is better at lying, you or me?
  9. What’s your funniest childhood memory?
  10. If you could choose one superpower, what would you choose and why?

Serious Questions To Ask Your Sibling

  1. Have you ever bullied anyone?
  2. Have you ever been bullied?
  3. Have you ever been in a fight?
  4. Who do you think mom and dad trust more out of the two of us?
  5. Have you ever had your heart broken by someone?
  6. If you could only choose one, would you put a stop to war or world hunger?
  7. What are you most grateful for?
  8. If you could change one thing about yourself physically, what would it be?
  9. What’s the worst thing you’ve ever said to mom or dad?
  10. What is your biggest fear in life?

Final Word

We hope you found this list of sibling questions useful and enjoy running through the questions when you are next with your brother or sister.

With a mix of light-hearted and more serious questions, they are designed to lead to funny, deep and meaningful conversations among siblings.

You probably already know your sibling as well as anyone, so where appropriate it may not be wise to ask certain questions that could bring up past memories that they don’t want to talk about.

So pick and choose as you please, try them out and enjoy having a really great conversation with your brother or sister!

Nick is a passionate dad who co-founded Rockinbaby to share his parenting journey with other new parents. He has a BSc and MBA, and works as a senior marketing professional. In his spare time Nick loves watching sports, staying fit and traveling. Learn more about Nick here.

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