1. What was their most prized childhood possession?

2. What did they do as a little kid that was super embarrassing?

3. What sports did they play growing up?

4. What did they want to be when they grew up?

5. What kind of treats did they always want on their birthday?

6. What was their favorite book as a kid?

7. What do you do that still drives them totally crazy?

8. What is something that completely changed about them as they got older?

9. What was the one thing about them everyone else commented on when they were young?

10. Where else did they apply to college?

11. Who was the person they thought they were going to end up with in high school?

12. Who did they take to prom?

13. What’s one of their go-to comfort foods?

14. What’s the best place they’ve ever traveled?

15. What outfit did they wear all the time as a kid that your parents still talk about?

16. Which one of your friends did they have a huge crush on?

17. What’s their favorite season?

18. What do they always disagree with your parents about?

19. What were they actually like in high school? Stoner? Goody two-shoes? Athlete?

20. What’s one present they’ll always be happy to receive?

21. What is their dream job now?

22. Do they want to get married?

23. Do they want kids, or a family?

24. Do they want to live in the same city as you one day?

25. What was their worst fear as a kid? Has it changed?

26. Do they have an athletic goal they’ve always wanted to achieve? (Like hiking the Appalachian trail or running a marathon?)

27. What are their weaknesses?

28. What is your go-to activity when you are reunited with them?

29. What’s their guilty pleasure TV show?

30. What was one embarrassing obsession of their childhood?

31. How do they like their eggs?

32. Are they team Bloody Mary, or team mimosa?

33. If you guys could take a sibling trip, no parents or other relatives or significant others, where would you go?

34. Are they super organized, messy/neat and fairly laid back, or a complete slob?

35. What is one giveaway sign that they are really stressed, really hungry, or really tired?

36. Are they good with technology?

37. Are they book smart or street smart?

38. Are they a chocolate person?

39. Do they prefer dogs or cats?

40. Do they want to live in the city, country, or suburbs of a city?

41. What kind of music do you both like to listen to (because it’s what your parents also listened to)?

42. What did they (or do they currently) major in in college?

43. Are they competitive, or are they the type of person who’s always supporting others?

44. Were they a teacher’s pet in elementary school?

45. Were they obsessed with their birthday growing up, or did they not like all the attention?

46. On a scale of one to 10, how much do they care about social media?

47. If you’re the older sibling, do(es) your younger sibling(s) feel like they’re always trying to fill your shoes? Or have they always known they wanted to be doing something different?

48. If you’re the younger sibling, do(es) your older sibling(s) feel like they need to be guiding you every step of the way, or do you they take a more hands-off approach?

49. Do they love to read, or would they rather spend Friday night catching up on their favorite shows?

50. When they were growing up, were they an introvert or an extrovert?

51. Are they an introvert or extrovert now?

52. What is something they have in common with your parents that you don’t share?

53. What is something you share with your parents (or other siblings) that they don’t?

54. What is one thing they wanted to accomplish when they were younger that they have now hit out of the park?

55. What are you most proud of them for?