60 Questions to Ask Your Sister (Funny, Deep and Nostalgic)

You can share a bedroom, a bathroom and a whole childhood with someone and still be surprised by how she answers a simple question. Sisters grow up side by side, then slowly turn into adults with their own routines, worries and favorite things. Asking good questions is one of the easiest ways to keep up with who she is now, not just who she was when you fought over the remote.

Below are 60 questions to ask your sister, grouped by mood. Use them on a long phone call, a road trip, a sleepover or a family dinner that needs rescuing. Some are silly, some are nostalgic and a few go deeper, so pick the ones that fit the moment.

Funny questions to ask your sister

Start light. These questions work best when you both answer and compare.

1. Which of us was the bigger drama queen as a kid?
2. What is the most embarrassing thing I have done in front of your friends?
3. If we swapped lives for a day, what would you do first?
4. Which family member would survive the longest in a zombie movie?
5. What is the weirdest food combination you secretly love?
6. Which of my outfits from the past should be burned?
7. What would your reality TV show be called?
8. If you could only text in emojis for a week, which three would you use most?
9. What is the worst gift you ever pretended to like?
10. Which of us would win a cooking competition, honestly?

Nostalgic questions about growing up

These are the ones that get you both laughing at the same memory, or arguing about who remembers it right.

11. What is your earliest memory of me?
12. What did we fight about most when we were little?
13. Which family holiday do you remember best, and why?
14. What toy or game did we play with the most?
15. Who got blamed for things the other one did?
16. What was the best hiding place in our house?
17. Which rule at home did you think was the most unfair?
18. What song reminds you of being a kid in our family?
19. Which teacher, neighbor or babysitter do you still think about?
20. What is something I did as a kid that you never told our parents about?

Questions about who she is now

People change a lot between twelve and thirty. These questions help you catch up with the grown-up version of your sister.

21. What does a perfect Sunday look like for you right now?
22. What is your comfort food after a bad day?
23. Which app do you spend way too much time on?
24. What is something you have become better at in the last year?
25. Who is the friend you text the most these days?
26. What are you currently obsessed with: a show, a song, a hobby?
27. What is one thing you always buy, even when money is tight?
28. Which chore do you hate the most?
29. Morning person or night owl, and has that changed?
30. What is the best advice anyone has given you lately?

Deep questions to ask your sister

Save these for a quiet moment. They are not interview questions, so share your own answers too.

31. When did you feel most proud of yourself?
32. What is something you worry about that most people don't know?
33. Is there anything you wish we talked about more?
34. What do you think our parents got right, and what would you do differently?
35. What is a moment when you felt really supported by me?
36. Is there a time I let you down that we never talked about?
37. What does being a good sister mean to you?
38. Which of your dreams from when we were younger do you still want?
39. What scares you about the next five years?
40. What do you want people to remember about you?

Would you rather questions for sisters

Quick-fire questions are perfect for car rides or group chats.

41. Would you rather live next door to me or in a different country?
42. Would you rather relive one day from our childhood or skip ahead ten years?
43. Would you rather share a bathroom with me again or share a car?
44. Would you rather go on a beach trip or a city trip together?
45. Would you rather have me plan your birthday or your wedding?
46. Would you rather know everything I think about you or nothing at all?
47. Would you rather our family group chat be silent or never stop?
48. Would you rather read my old diary or let me read yours?
49. Would you rather have a matching tattoo or matching pajamas?
50. Would you rather cook a family dinner or clean up after it?

"How well do you know me?" questions

These questions test whether your sister has been paying attention. They are also the backbone of a good sister quiz.

51. What is my coffee or tea order?
52. What am I most afraid of?
53. Which pet would I choose?
54. What is my role in the family group chat?
55. Where would I most like to live?
56. What do I do when I am angry?
57. Which vacation would I pick?
58. What am I always late for?
59. What would I grab first if the house was on fire?
60. What is my best quality?

Turn these questions into a sister quiz

If you want to see how many of those last ten questions she actually gets right, make it a game. With our free Sister Quiz you answer 10 questions about yourself, get a link, and send it to your sister. She guesses what you picked, and her score shows up on your scoreboard. Brothers, cousins and friends who are basically family can take the same quiz, so you can find out who really knows you best.

A few tips to make it more fun:

• Answer honestly. The quiz is only interesting if your answers are really yours.
• Skip questions that are too easy. If everyone knows you hate spiders, skip that one and pick something she has to think about.
• Swap afterwards. Once she has taken yours, ask her to make her own and see if you can beat her score.

However you use these questions, the point is the conversation. The best answers usually come with a story attached, and those stories are what make sisters such good company.