101+ Questions to Ask Siblings

What are some good questions to ask Siblings?

Are you meeting your siblings again after a long time apart? You may have grown up together, but that doesn’t mean you know each other well, does it? After all, you went your separate ways some time back. Much has changed for both of you, and there’s much catching up to do.

That’s great, of course—that means there are many pleasant conversations to be had. And by using the questions we collected in this article, your discussions with your sibling will be funnier, more interesting, and more revealing than ever before.

Check out the questions below, take your picks, and enjoy reliving the good times with your siblings.

Questions To Ask Your Siblings About Yourself

These questions test how well your sibling knows you. Who knows what long-harbored secrets and feelings they’ll reveal about you? For fairness’ sake, you can let them ask you the same question.

Questions To Ask Your Siblings About Yourself
  1. What’s your favorite childhood memory of us growing up together?
  2. Did you like me being older or younger than you?
  3. What is the most reckless thing I’ve ever done, in your opinion?
  4. Was I a bully to you when we were growing up?
  5. Was there anything about my personality that really got on your nerves? Does it still annoy you now?
  6. Do I have anything in my life that you want but don’t have yet?
  7. Let’s see if you still remember the old me. Who was my celebrity crush?

Reading Suggestion: 5 Signs You Have A Narcissistic Sibling

Questions About Childhood

It’s always nice to talk about your childhood when you and your siblings enjoyed simpler times. Don’t be surprised if these questions lead to one funny, nostalgic story after another:

Questions About Childhood
  1. When you were still a child, what was your favorite toy?
  2. Did you ever have an imaginary friend? Who was it?
  3. As a kid, what cartoon or TV show did you drop everything you were doing to watch?
  4. Did you ever go to summer camp?
  5. In school, were you the “teacher’s pet” type… or did you get sent to the principal’s office a lot?
  6. Do you have any funny stories involving our parents during childhood?
  7. How would you describe our family dynamic when we were kids?
  8. Was there anyone in our family who gave you tough love that shaped who you are now?
  9. What childhood memory still makes you laugh uncontrollably today?
  10. When you were a kid, did you cause problems for other kids?
  11. Did you fight with others a lot as a youngster?
  12. What were your childhood nicknames?
  13. What was your most embarrassing childhood memory?
  14. Have you ever done anything our parents are still unaware of?
  15. When did you first fall in love with someone in school?
  16. What is the most mortifying experience you remember about me when we were kids?
  17. Do you ever wish I stood up for you more?
  18. Were you ever in competition with me growing up?
  19. Do you think our parents loved either of us more, and did that create jealousy between us?
  20. What is the last big thing we did together as siblings?
  21. What was the most memorable argument we had as kids?
  22. Did you ever fall in love with someone who I also liked/dated?
  23. Who was your best friend growing up? What was so special about them?
  24. Who was your favorite teacher? Why did you like them so much?
  25. Who was your first crush? Where are they now?

Reading Suggestion: Narcissistic Sister: Help! My Sister is a Narcissist

“Do You Know Me” Questions for Siblings

Feel like playing a game with your sibling? Ask them these questions and see how deeply they know you (or not). Of course, it’s only fair if they throw the question back at you. Be ready to put your knowledge of your siblings to the test.

“Do You Know Me” Questions for Siblings
  1. What was my favorite home-cooked meal?
  2. What were my three favorite snacks at home?
  3. What was my favorite thing to eat for breakfast?
  4. What was my go-to outfit when I didn’t know what to wear?
  5. What was my first pet’s name, and what happened to it?
  6. How many countries have I gone to?
  7. Who was my first boyfriend/girlfriend?
  8. What was my favorite movie growing up?
  9. When was the last time you made me cry?
  10. How long did my first relationship last?
  11. When was the last time I was unexplainably sad?
  12. What was the worst thing that happened to me as a kid, and how did it make you feel afterward?
  13. Did anything happen to your emotional well-being while growing up that made you feel like something had gone horribly wrong?

Reading suggestion: Narcissists In The Family

“Who’s Who” Sibling Questions

Now that you’ve caught up with each other a bit, it’s time to ask the theoretical questions. Based on your new knowledge of each other, who is better or worse than the other at certain things? It’s time to find out:

“Who’s Who” Sibling Questions
  1. Which of us is more likely to end up in jail and why?
  2. Which one of us can drink the most without getting drunk?
  3. Which of us is better at cooking?
  4. Who’s worse at keeping secrets?
  5. Who’s more likely to become the CEO of a multi-million dollar business?
  6. (If you’re both still single) Are you more likely to get married before I do?
  7. Who can speak more languages fluently?
  8. Who is the better singer among us?
  9. Who is lazier among us?
  10. Who’s funnier—you or me?
  11. Who between us is more likely to get into an embarrassing accident within the next year?
  12. Who is better at stress and controlling their temper—you or me?

Reading Suggestion: 7 Proven Ways How to Deal With a Controlling Sister in Law

“Would You Rather” Questions For Siblings

If you’d rather not talk about serious stuff with your siblings (or at least not yet), whip out these “would you rather” questions and just have silly conversations with them. These might even uncover a funny story or two.

“Would You Rather” Questions For Siblings
  1. Would you rather have no nose but never have bad breath, or be blind but have supermodel looks?
  2. Would you rather learn to speak any language of your choice fluently… or instantly gain a superpower of your choosing?
  3. Which would you choose: the ability to tell someone’s future… or to read their mind?
  4. Would you rather always feel hot or always feel cold?
  5. Which would you rather give up: music or books?
  6. Would you rather never be able to wear your favorite outfit again… or only be able to wear it and nothing else for the rest of your life?
  7. Would you rather eat only your favorite food and nothing else every day for the rest of your life… or be able to eat anything you want except your favorite food?
  8. Would you rather go bald or have crazy hair growth that can’t be controlled?
  9. Would you rather forget everything that happened in the past five years or never be able to remember anything that will happen in the next 5 years?
  10. Would you rather eat your most disliked food once… or get lectured by mom one more time?
  11. Would you rather hear the neighbors quarrel for hours or hang out with the bullies in your high school?
  12. Would you rather I chose what you wore for a week, or should mom do it for you?
  13. Would you prefer to see 1 hour into the future or return to your childhood years?
  14. Would you rather have to sing along to every song on our family trip or dance to all of them at our family gatherings?
  15. Would you rather have given up your room or toys when we were kids?
  16. Would you rather go back to fix the mistakes you made in the past or be able to tell the future?
  17. Would you rather be a wealthy noble 200 years ago or just an average person today?
  18. Would you rather always stink and not know it or always smell everyone else’s stink?
  19. Would you rather your life have a rewind button… or a pause button?
  20. Would you rather be neighbors with your favorite celebrity… or get your dream job?
  21. Would you rather have a giant head or a tiny body?
  22. Would you rather be boring for the rest of your life—or annoying for the rest of your life?

Reading Suggestion: How to Deal with a Narcissistic Brother? 5 Tips That Truly Help

Weird Questions To Ask Your Sibling

In this section, we got totally random questions. If you feel like asking each other silly nonsensical queries and see what answers you get, try these weird questions out:

Weird Questions To Ask Your Sibling
  1. If you could choose to be either a superhero or a supervillain, which would you be?
  2. If you were cursed to live as an animal for the rest of your life, what animal would you choose to become?
  3. Did you hear the voices in our old house too?
  4. What would you be if you were one of the snacks we used to eat as kids?
  5. Did you steal anything from me in the past and never came clean?
  6. Who would it be if you could kill or maim someone and get away with it?
  7. Did you know you talked while you slept?
  8. If you were cursed to eat just one kind of food for the rest of your life, what would it be?
  9. If you were a fart, would you be the hot and quiet type or the loud and boisterous type?

Reading Suggestion: 13 Signs He Told his Friends About you

Deep Questions To Ask Your Sibling

Lastly, if you feel like getting real personal with your siblings, switch to asking deep questions to each other. These questions reveal your feelings about the past, present, and future:

Deep Questions To Ask Your Sibling
  1. What do you think would be your dream vacation destination?
  2. If you could speak any language fluently, what would it be?
  3. What would you do if you found out you were adopted?
  4. In your opinion, what are you proudest of in our family history?
  5. Do you have anxiety problems?
  6. What do you admire the most about our parents?
  7. What’s the weirdest dream you’ve ever had?
  8. Would you ever want to see a ghost?
  9. What’s your most embarrassing moment?
  10. If you had to give up your dream job to change your worst childhood memory, would you do it?
  11. If a genie offered to change anything in our childhood, what would it be?
  12. What’s the worst thing that’s ever happened to you?
  13. In what ways did our parents let you down?
  14. Is there something you want to do in your life that you’re scared you won’t be able to do? What is it?
  15. What, in your opinion, is the most life-changing moment of your childhood, and how do you think it shaped you into the person you are today?
  16. What, in your opinion, was the most rebellious thing you’ve ever done in your life?
  17. Do you consider yourself successful enough?
  18. What’s the single most important political or social issue for you?
  19. What was your single biggest insecurity as a young person, and does it still bother you to this day?
  20. What movie scene or song from your childhood still makes you cry even today?
  21. How do you feel about us getting older?
  22. How do you think our family would be different if we had different parents?
  23. Do you have any regrets in life? If so, what are they?
  24. Who is your role model (outside of our family)? Why them?
  25. What would you say is your biggest accomplishment?
  26. What are your fears, and why?
  27. When things get tough, what motivates you?

Reading Suggestion: How to Deal With Your Narcissistic Sibling?

What are Some Good Questions to Ask Your Siblings?

The questions in this article can be used for siblings to get to know each other better, even if you spent most of your childhood together. They’re all meant to do one thing: to lead to longer, deeper, and funnier conversations.

A word of caution, though: Some questions may be inappropriate, especially if they bring back unpleasant memories for your sibling. It’s hard to predict which personal questions will do that.

What are Some Good Questions to Ask Your Siblings

We suggest you stick to the more straightforward, more lighthearted queries first—such as those in the “childhood,” “who’s who,” and “would you rather” sections.

Then, when you sense your sibling has no issues with talking about the past, you can try out the “deep” and “do you know me” questions to strengthen your bond even further.

Reading Suggestion: Do Narcissists Love Their Children?

All-in-all, these interesting questions to ask siblings have the same purpose: to give you and your siblings a stronger relationship than you had before the conversation. Try them out—they just might form a new favorite memory for both of you. Good luck!

Last Updated on September 1, 2022 by Alexander Burgemeester

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Alexander Burgemeester

Alexander Burgemeester has a Master in Neuropsychology. He studied at the University of Amsterdam and has a bachelor's in Clinical Psychology. Want to know more?

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