1. What’s the most rebellious thing you did growing up?
2. What does your ideal idyll afternoon look like?
3. If you had to pick a “spirit animal,” what would it be?
4. If you could switch careers without any concern for money, what would you do?
5. What makes you smile without fail?
6. What about your teenage self embarrasses you most?
7. What’s your favorite thing to do when you’re totally alone?
8. Have you ever had your fortune told by a psychic or a Tarot card reader and if so, what did you learn?
9. What’s your family’s weirdest tradition?
10. When’s the last time you failed spectacularly at something?
11. When’s the last time you stayed up all night?
12. What was your weirdest interest or hobby as a kid?
13. Do you have any irrational fears and if so, what are they?
14. What’s the funniest or most traumatic thing that’s ever happened to you on a date?
15. What’s your earliest childhood memory?
16. Which of the places you’ve traveled to inspired you the most, and why?
17. Have you ever been caught lying?
18. What’s the last white lie you told and got away with?
19. When’s the last time you felt seriously disappointed?
20. What’s the creepiest dream you’ve ever had?
21. Have you ever left someone you still loved?
22. Do you believe in the concept of “the one”?
23. Do you believe in fate?
24. What’s the most bizarre situation you’ve ever walked into?
25. Have you ever had a mentor?
26. Do you consider yourself a mentor to anyone right now?
27. What made you decide to study [insert college major]?
28. What impacts your moods more than anything else?
29. What’s your greatest talent?
30. If your job isn’t your passion, what is?
31. How do you really feel about your boss?
32. Are you a risk taker or someone who’s more risk averse?
33. Do you prefer group dinners or one-on-ones with friends?
34. Who do you trust more than anyone else?
35. Which of your family members do you admire most, and why?
36. Did you feel closer to your mom or dad growing up?
37. Are you more into your zodiac sign or your MBTI?
38. Is there a talent or skill you’ve always secretly wanted?
39. Under what circumstances do you tend to feel shy?
40. Where would you live if you had no ties to any specific place?
41. Which good cause is closest to your heart?
42. If you could change one thing about yourself, what would it be?
43. If you could change one thing about your past, what would it be?
44. Do you have any secret untapped passions?
45. When’s the last time you really indulged, and for what occasion?
46. What age do you hope to live to?
47. What’s the most disturbing thought you’ve ever had?
48. If reincarnation was definitely a thing, what form would you want to take on in your next life?
49. Which famous person, dead or alive, would you most like to know?
50. What’s the most memorable thing that’s ever happened to you (up until you met me, of course)?