357 Best Questions to Ask Your Sister (to Really Know Her)

Are you looking for questions to ask your sister? You have found the right place!

We have prepared for you a huge collection of questions divided into several categories: funny, deep, juicy, about relationships, about career, about friends, about hobbies, and more…

You can jump directly to your favorite category:

Funny Questions to Ask Your Sister

  1. Have you ever been so drunk that you don’t even remember what happened during that day or night?
  2. What is that one joke that always cracks you up?
  3. Do you laugh when someone falls from the stairs?
  4. Have you ever stolen something from the grocery store when you were a kid?
  5. Out of all your siblings, who is your favorite?
  6. If you can rank your siblings, on what number I would be?
  7. Have you ever teased someone so bad that they got you to the police? 
  8. Would you allow me to do your makeup in a blindfold? 
  9. Have you ever wandered naked in your home? 
  10. Have you ever pranked your mom by telling her that you are a gay or a lesbian? 
  11. How often do you wanna annoy me?
  12. Have you ever escaped from household chores?
  13. What instrument do you think is the most annoying?
  14. What's the most useless word?
  15. What's the worst food mom prepared?
  16. What's something that you find funny about our parents?
  17. Have you ever farted in front of mom/dad?
  18. Have you ever pranked our parents?
  19. Who snores the most and loudest in our family?
  20. Have you ever skipped classes?
  21. What makes you bored at home?
  22. What prank would you want to pull on our parents next time?
  23. Are you scared of mom, dad, or nah?
  24. Have you ever stolen cash from mom and dad?
  25. Who do you look like in the family?
  26. Have you ever broken something at home and never caught?
  27. What usually makes you laugh when we’re together?
  28. Who do you think is the favorite child?
  29. Would you dare steal cash from them with me?
  30. Who’s the laziest around the house?
Funny Questions to Ask Your Sister

Questions to Ask Your Sister about Relationships

  1. Do you remember your first crush? Who was he and what was it like?
  2. Was your crush your first love too?
  3. What is the first song that comes to your mind when you think about our relationship? 
  4. If I ask you to look for a spouse, would you accept?
  5. Did you have a serious relationship while in high school? Why did it end?
  6. What was your first impression of your partner?
  7. What did you like or love about your partner?
  8. Do you still like what you loved about your partner and why?
  9. Are you happy with the intimacy you share with your partner?
  10. Do you feel the same way you felt for your partner at the beginning of the relationship?
  11. How do you feel when others find your partner attractive?
  12. Do you feel jealous if your partner hang out with a friend of the opposite sex?
  13. Do you make sacrifices for your relationship?
  14. Have you ever apologized for what you’ve done wrong to your partner?
  15. Do you forgive your partner’s mistakes easily?
  16. Will you say sorry to your partner even though it’s not your fault?
  17. Are you willing to compromise your happiness for a successful relationship?
  18. What makes you happier in a relationship, sharing or sacrificing?
  19. If you could choose your partner again, would you choose the same person?
  20. When it comes to future, do you and your partner have the same relationship goal?
  21. How do you find dating apps?
  22. What does your ideal relationship look like?
  23. What is the best thing about dating you?
  24. What is the worst thing about dating you?
  25. What was your biggest heartbreak?
  26. How do you forgive someone who betrayed you?
  27. Have you ever begged for a second chance?
  28. What’s the worst relationship you’ve been on?
  29. What’s the best relationship you’ve been on?
  30. Have you ever been cheated on?
Questions to Ask Your Sister about Relationships

Questions to Ask Your Sister about Family and Friends

  1. How many kids would you like to have OR how many number of kids you think are sane to have?
  2. What is the first song that comes to your mind when you think about our relationship? 
  3. Have you ever pranked your mom by telling her that you are a gay or a lesbian? 
  4. What thing do you mostly lie about to our parents?
  5. What member of our family did you try to keep me away from?
  6. How does mum/dad make you laugh?
  7. What is it that dad/mum often tell you?
  8. What do you like most about your grandparents?
  9. Who among our parents was against you going to parties?
  10. Would you report your best friend to the police for doing an unlawful thing?
  11. Imagine that you have friends in several countries, how would you ensure that you are always in touch?
  12. Were there tasks you hated doing when you were a child?
  13. Is there anything that you're ashamed of about our family?
  14. Are you willing to take risks for our family?
  15. Have you ever compared your friendships to our family relationship?
  16. Were there times when our parents unknowingly hurt you?
  17. Have you ever ended a friendship?
  18. Do you treat your friends as your family?
  19. What do you think is lacking in our family?
  20. Do you wish our parents to treat you differently?
  21. Do your friends have any strange hobbies?
  22. What's the most interesting thing about our family?
  23. What's something boring about our family?
  24. Who's our funniest family member?
  25. Who do you consider the funniest among your friends?
  26. Have you ever thought of moving away from our family?
  27. What do your friends have to say about our family?
  28. How do your friends comfort you in difficult times?
  29. Do you think we’re close enough with our parents?
  30. Have you ever been betrayed by a friend?
Questions to Ask Your Sister about Family and Friends

Questions to Ask Your Sister about Education and Career

  1. Do you receive enough educational support from our family?
  2. Why did you decide to go for that major?
  3. Did our parents influence your choice of education?
  4. Would you stop studying if our parents suddenly couldn't support your finances?
  5. Has anyone ever bullied you in school?
  6. Do you dream of becoming an educator?
  7. What's the worst thing you encountered in school?
  8. What's your best educational advice for the younger generation?
  9. Have you ever applied for scholarships and get declined?
  10. What's the best advice a professor has given you?
  11. What do you do at home when you're stressed out from school?
  12. Are our parents good teachers?
  13. What are the most important values your school taught you? 
  14. Have you ever thought of dicontinuing your education?
  15. How do you describe yourself as a student?
  16. Why did you choose that career path?
  17. Did you have a discussion with our parents about your chosen career?
  18. Do you have plans of starting up a business?
  19. How do you decribe your boss?
  20. Have you ever been into an argument with a colleague?
  21. Would you like to work overseas?
  22. Would you want me to follow your career path?
  23. What is the worst job you have ever had?
  24. What do you think is your greatest strength?
  25. What's the worst career decision you've ever made?
  26. What's the best career decision you've ever made?
  27. What do you think are the secrets behind getting to where you’re at?
  28. How do you make decisions?
  29. How does our parents affect your decisions?
  30. Have you ever regretted a career decision you made?
Questions to Ask Your Sister about Education and Career

Questions to Ask Your Sister about Hobbies and Interests

  1. Do you have any favorite comic books?
  2. Who is your favorite fictional character of all time?
  3. Do you happen to have a favorite YouTuber?
  4. Which band or singer is your favorite?
  5. Which character would you like to play if you were in a movie?
  6. What do you enjoy doing together with me?
  7. What activities have you enjoyed as an adult?
  8. What are you interested in outside of work?
  9. What is a hobby that you would like to take up in the future?
  10. How would your hobbies be different if we were rich?
  11. Have you made any new friends while doing one of your hobbies?
  12. Do your friends have any strange hobbies?
  13. What is a hobby that you would be scared to try? 
  14. Are there any hobbies that you feel are a waste of time?
  15. What kinds of hobbies would you like our family to do?
  16. When was the last time you lost interest on something?
  17. What hobby of mine do you not find interesting?
  18. Do you like it when someone sings at home?
  19. How often do you like to exercise?
  20. Do you enjoy watching movies with our family?
  21. What do you really hate having to do in your free time?
  22. Do you ever feel that you waste your free time? How?
  23. What movies are you most interested in?
  24. What books would you recommend me to read?
  25. Would you rather go to beaches or mountains?
  26. How do you fight boredom at home?
  27. What is something that you’d like our family to try doing?
  28. When does a hobby become boring?
  29. When do you have most fun at home?
  30. What interests you the most at work?
Questions to Ask Your Sister about Hobbies and Interests

Deep Questions to Ask Your Sister

  1. What’s been the best day of your life so far?
  2. If you could meet anyone in the world, alive or dead, who would it be?
  3. What is one thing you’ve never told me?
  4. What’s something our parents don’t know about you?
  5. Is there something you can’t live without?
  6. What’s your most prominent childhood memory?
  7. Is there something I did that you’ve never gotten over, or forgiven?
  8. What’s one piece of parental advice that you’ve held onto?
  9. What’s your greatest fear in life?
  10. What would you change, if anything, about our experience growing up?
  11. What do you admire most about Mom and/or Dad?
  12. In what ways did Mom or Dad let you down?
  13. How could I have been a better sibling to you when we were growing up?
  14. Who was the first person to break your heart?
  15. Were you ever bullied? Did you ever bully anyone?
  16. What was your biggest insecurity as a teenager?
  17. What’s your love language?
  18. What’s the most rebellious thing you’ve ever done?
  19. How do you feel about getting older?
  20. Was there any situation where you wish I stood up for you?
  21. Were you ever in competition with me?
  22. Is there anything you hate about me?
  23. What do I have that you don't, but wish you had too?
  24. Did you ever fall in love with the same person as I did?
  25. Were you ever depressed?
  26. Did you ever feel like you were abused emotionally by a family member?
  27. Do you want to get married?
  28. What is your weakness?
  29. Did you have any fear as a child? Did it change?
  30. Is there anything you wish you told me when you were younger and were too scared to?
Deep Questions to Ask Your Sister

Juicy/Dirty Questions to Ask Your Sister

  1. When was your first kiss?
  2. To whom did you give your first kiss?
  3. At what place did you have your first kiss?
  4. Have you ever wandered naked in your home? 
  5. Have you already lost your virginity?
  6. What turns you on?
  7. What do you look for in a man?
  8. Do you sleep without clothes on?
  9. Has anyone not part of our family seen you naked?
  10. What's your view of one-night stand?
  11. Where is your favorite spot to be kissed?
  12. How do you feel about kissing in public?
  13. What’s your favorite pair or underwear?
  14. Are you a snuggler?
  15. Have you ever seen a man naked?
  16. What do you expect most out of a relationship?
  17. What is your guilty pleasure?
  18. Have you ever flirted with a stranger online?
  19. Do you invite someone in on the first date?
  20. Do you think lovemaking should happen anywhere, not just in a bed?
  21. Are you a romantic?
  22. What are your thoughts on casual sex?
  23. What does the word sex mean to you?
  24. What is your biggest turn-off?
  25. Do you watch videos with explicit contents?
  26. How important is sex education to you?
  27. Have you already slept with someone we don’t know?
  28. Do you prefer having small or big boobs?
  29. What is sexy for you?
  30. What kind of figure do you want in men?
Juicy/Dirty Questions to Ask Your Sister

Questions to Ask Your Sister about Me

  1. Do you think mom and dad love me more than you?
  2. Do you love me?
  3. What habits of mine irritate you the most?
  4. What do you think of me?
  5. Were you ever in competition with me?
  6. Which animal scares me the most? 
  7. How many pairs of shoes do I own? 
  8. Am I a good sister according to you?
  9.  What is my comfort food?
  10. At what age did I pierce my ears? 
  11. Which bad habit have I been trying to quit for years?
  12. The first time I was admitted to the hospital was because of what?
  13. What is my favourite fruit? 
  14. What’s my most annoying habit or quality?
  15. What things I hate the most?
  16. What memory of us still makes you laugh?
  17. What is my favourite pizza topping? 
  18. Will you switch places with me?
  19. Who would I like to meet in person?
  20. What is my spirit animal? 
Questions to Ask Your Sister about me

Weird/Embarassing Questions to Ask Your Sister

  1. How did you lose your virginity?
  2. Did you ever fall in love with the same person as I did?
  3. Was your crush your first love too?
  4. When was your first kiss?
  5. To whom you give your first kiss?
  6. At what place did you have your first kiss?
  7. At what age did you tell mom and dad about drinking?
  8. Have you ever stolen something from the grocery store when you were a kid?
  9. What is your guilty activity?
  10. Have you ever kissed someone you are not supposed to do? 
  11. Do you have the guts to ask your crush out? 
  12. Have you ever teased someone so bad that they got you to the police? 
  13. Have you ever wandered naked in your home? 
  14. About whom do you gossip the most?
  15. What thing do you mostly lie about to our parents?
  16. What is the most awkward and embarrassing moment in your life?
  17. Have you ever fallen into the sewage?
  18. Have you ever farted in front of mom/dad?
  19. Have you ever skipped classes?
  20. Is there anyone who cheated on you?
  21. Have you ever cheated in a relationship?
  22. Do you sleep without clothes on?
  23. What does the word sex mean to you?
  24. Do you enjoy talking about sex?
  25. What is your biggest turn-on?
  26. Do you watch videos with explicit contents?
  27. Have you ever tripped in public?
  28. How do you cope from an embarassing situation?
  29. Have you ever embarrassed anyone?
  30. Have you ever fell asleep in public?

Check our other good collections:

Funny Questions to Ask Your Sister

Deep Questions to Ask Your Sister

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