39 Eye-Opening Questions To Ask Your Sister To Really Know Her

There’s something special about the bond you hold with your sister.

She might be a full-blood sister, half-sister, stepsister, adopted sister, foster sister, or even your soul sister.

It doesn’t matter if you’re best friends or you fight like cats and dogs, you’re many years older or younger, or you’re the same age, or if you grew up in the same house–she’s family, and you love her. 

Regardless of how close you are, these questions for sisters will help you get to know her better. 

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39 Questions to Ask Your Sister to Really Know Her

Do you want to deepen your bond with your sister? Or maybe you’re just looking to have some fun or reminisce about the past? 

Either way, there are plenty of questions to ask sisters to get the conversation flowing.

Random Questions to Ask Your Sister

1. What are the top three things on your bucket list?

You could learn surprising things about your sister’s goals and dreams in life, such as her desire to write a novel, learn to fly a plane or go scuba diving. 

2. What’s your most vivid childhood memory?

Even if you grew up together, you most definitely experienced childhood differently. Good or bad, she might remember things you have long forgotten or never even knew about to begin with.

3. Do you have any hidden talents?

Your sis may secretly be a world-class juggler, a master yodeler, or a speed reading queen. Make sure to ask follow-up questions about when and how she learned this talent of hers. 

4. If money wasn’t an issue, what would be your dream vacation?

It’s always nice to get away, even if it is just daydreaming about an escape to a tropical island with her favorite people and nothing but the best foods, drinks, entertainment, accommodations, and service. 

5. What is your most memorable birthday as a child? 

Birthdays are a time to feel special and celebrated. What made your sister’s birthday so memorable? How old was she? Who was there? What was the celebration like? Was it a surprise?

6. What do you most admire about Mom/Dad?

You’re two very different people and probably hold very different opinions of your parents. What did she like most about them growing up? How does that compare to what you admired most?

7. What’s your funniest memory of us together?

Get a little nostalgic and compare memories you each have of your time together. Relive hysterical moments from your childhood or more recent experiences as adults.

8. What, if anything, would you change about our experience growing up?

Take a trip down memory lane and talk about things that affected each other growing up. Does she wish your parents wouldn’t have moved the family across the country in third grade?

Would she vote for the swimming pool instead of the family trip to Sea World that one summer?

9. What’s something you did as a kid that mom and dad never found out about?

If you’re looking for juicy questions to ask your sister, this is a good one. Sharing secrets is a good way to strengthen the bond between you. Besides, it’s not like they can ground her now. 

10. Have you ever been bullied or been a bully to someone else?

Bullies are an unfortunate part of life. Maybe the way she was treated in high school shaped her into the kind, compassionate person she is now. Or perhaps she’s not proud of how she picked on the special needs kids at summer camp.

11. What was the most embarrassing moment in your life?

Share some laughs with stories about your most embarrassing memories, either from childhood or as an adult.

Maybe it was when she fell off the stage during her ninth-grade chorus concert or the time at work she used the men’s bathroom, clogged the toilet, and had to call maintenance. 

Juicy Questions to Ask Your Sister

12. Have you ever cheated on a partner?

Another tough one to own up to, especially if it was on a current partner who is unaware of her indiscretion. If she confesses to this, it’s important to honor her trust and keep it to yourself.

13. How old were you when you lost your virginity, and who was it with?

This one might not be a suitable question for every sibling relationship. Personal questions like this require a certain level of trust and openness between you. Only ask this if you are willing to answer it in return. 

14. What do you wish everyone knew about you?

If she’s like most people, there is probably something she wishes others knew about her that would make them understand who she is and why.

15. Have you ever stolen anything?

This one takes guts to admit if the answer is yes. If you’re willing to ask the question, you have to assure her you won’t judge her for her answer. 

16. Who was your first kiss, and when was it?

Did it make her foot pop like Anne Hathaway’s in The Princess Diaries or was it during an awkward game of truth or dare in front of a group of kids watching and giggling?

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17. What’s your favorite comfort food?

Even if you know her favorite food is chicken and broccoli alfredo, she might reach for loaded BBQ pulled pork nachos from the pub near her house when she feels down or stressed.

18. What is your all-time favorite movie?

There are so many good movies that it can be hard to narrow it down to just one favorite. Limit it to a specific genre or time period, or have her pick her top five if she has trouble choosing.

19. If you could be invisible, where would you go, and what would you do?

Would she spy on her kids or partner? Sneak into a Broadway show? Visit her quarterback crush in the locker room after game time?

The answers to this one could lead to some shocking revelations– and loads of laughs.

20. Who is your favorite celebrity?

Lighten the mood with chatter about who she admires and why. It could be an actor, a musician, an artist, an author, a social media influencer, or any other person in the spotlight. 

21. What is your dream job?

Her dream job may be nothing like what you expect. She could shock you with her secret desire to be a Hollywood movie star, international flight attendant, chef, and owner of an upscale restaurant in a big city.

22. How do you handle stress?

Everyone responds differently to trying times. How does your sister deal when crap hits the fan, or everything around her falls apart? You might uncover things you have in common or pick up some healthy coping mechanisms.

23. If you could travel back in time, what year would you go to and why?

She might revisit a certain time in her life for a do-over, or it could be a whole different era full of new experiences and ways of life. The possibilities are endless.

24. What is your biggest fear?

Is her phobia common, like heights, spiders, snakes, dogs, or flying, to name a few? Maybe she fears something less common such as balloons or the color yellow. Or perhaps her biggest fear is an experience like speaking in public.

25. What worries keep you up most at night?

Learn about the things that bother her most. Is it the lack of a college fund for her kids? A secret desire to change careers? The scary events on the daily news? 

26. What’s your favorite thing to do when you’re alone?

Maybe alone time is a foreign concept to her or something she rarely gets to experience. Does she prefer to spend that time watching Lifetime movies with a tub of ice cream and a bottle of wine? Or would she rather hike her favorite trail?

27. What is your weirdest habit?

Just about everyone does things that others consider strange. Does she bite off the ends of her Bugles before she eats them?

Always count her steps when she walks? Talk to herself? You could learn something interesting and funny about her with this one.

28. Do you believe in ghosts/paranormal activity?

Her belief could range from an obsession with everything haunted to uncertainty around personal experiences to absolute confidence there’s no such thing as ghosts, or it could be anything in between.

It might be cool to compare your beliefs and any reasons for having them. 

29. What is my biggest pet peeve?

You can turn around the “how well do you know your sister” questions and quiz her to see how well she knows you.

Is she aware how much you despise being interrupted or how disgusted you are by the sound of someone chewing with their mouth open?

30. What is your favorite thing about me?

It always feels good to hear nice things about yourself. Find out what it is about you that she admires most. And, of course, tell her your favorite things about her. 

31. Which of us do you think is more optimistic?

Some people see the glass as half full, and some see it as half empty. The world needs both kinds. Which of you is more likely to see the positive and which is more likely to point out what’s wrong?

Funny Questions to Ask Your Sister

32. If you could have a superpower, but it had to be completely useless, what would you pick?

Let your sister's imagination run wild with this fun prompt that encourages her to think of a desirable but ultimately pointless superpower. Her answer is sure to be entertaining and may even surprise you!

33. Would you rather fight one massive duck or a hundred tiny horses?

Present a ridiculous scenario for her to imagine. She'll have to weigh the pros and cons of fighting a giant duck or a swarm of miniature horses, and hearing her reasoning behind her choice is sure to get everyone laughing.

34. If you were a vegetable, which one would you be and why?

Add a silly twist to a classic prompt by asking her to imagine herself as a vegetable. Her answer will give you an insight into her personality and sense of humor and may even spark a playful debate!

35. If animals could talk, which one do you think would be the most obnoxious?

This prompt is a playful take on the idea of anthropomorphizing animals. Your sister will have to ponder which animal would be the most unpleasant if it could suddenly start talking. Would she choose something terrifying like a shark? Or something benign but funny like a jackass?

36. If you had to choose one food to eat for the rest of your life, what would it be?

Make your sister imagine a life without variety in her diet. She'll have to consider what food she likes enough to eat for every meal, every day for the rest of her life. Her answer is sure to spark some creative and imaginative responses and debate between you.

37. If you could switch lives with any fictional character, who would you choose?

Encourage your sister's imagination with this fun prompt. She'll have to decide on a fictional world she'd like to live in and what character she would like to be. If you know your sister's favorite books or movies, you may have an idea about what she might answer.

38. Would you rather be able to fly or be invisible?

This prompt asks your sister to pick between two popular superpowers, both of which come with their own pros and cons. She'll have to weigh the benefits of being able to fly against the benefits of being invisible. Which one would you choose?

39. If you could eliminate one chore from your life forever, what would it be?

This prompt is a playful take on the mundane realities of everyday life. Your sister will have to consider which of her many chores she hates the most and imagine what it would be like to never have to do it again. Hopefully, it's not something you'll have to take over!

Final Thoughts

Not every question will be appropriate for your situation, of course. Use your judgment to decide what sister questions work best for you, and make a point to get to know her better. You can always work up to more personal topics as you both become more comfortable.