2. What’s your favorite childhood memory?
3. Are you close with your parents?
4. Have you been in love before? Who was your first love?
5. When was your first kiss?
6. When was your last relationship, and how did it end?
7. Have you ever been to therapy?
8. What’s the kindest thing someone’s ever done for you?
9. What’s the hardest thing you’ve ever had to do?
10. Do you believe in soulmates?
11. Have you ever had your heart broken?
12. Have you ever broken someone else’s heart?
13. Are your parents together?
14. What’s your love language?
15. Do you have any phobias?
16. What were you most scared of as a kid?
17. What’s your biggest fear now?
18. Is the approval of others important to you?
19. When was the last time you felt inspired to create something? What’d you create?
20. How do you like to be comforted when you’re sad or upset?
21. Who in life do you look up to most?
22. What’s the most rebellious thing you’ve ever done?
23. What’s something you’d like to learn more about?
24. Do people trust you to keep secrets?
25. How did your parents meet?
26. How would you describe your approach to conflict resolution style?
27. Do you think it matters more what we achieve or who we surround ourselves with?
28. What are your coping tools for dealing with stress or anxiety?
29. What would you consider your proudest accomplishment to be?
30. What do you think happens when we die?
31. What do you think you’ll be like in old age?
32. What’s something you’re unwilling to compromise on?
33. Have you ever been cheated on?
34. What traits do you think are most important to find in a partner?
35. What type of partner do you consider yourself to be?
36. What do you like most about yourself?
37. What’s one thing about yourself that you’d like to change?
38. Who in your family are you closest to?
39. Whose relationship do you admire and why?
40. What’s the worst thing about dating today?
41. Would you consider yourself a Relationship Person, or someone who’s generally more comfortable single?
42. What’s been the most eventful year in your life so far?
43. What’s something you see as being a relationship dealbreaker?
44. Would you consider yourself naturally trusting or a more guarded person?
45. Do you fall in love easily?
46. Are you a quantity or quality person when it comes to your friendships?
47. Who’s your oldest friend?
48. What’s something you’d like to do differently in your next relationship?
49. What’s something you wish you had a do-over on?
50. Would you rather have a job that’s just a job but pays well, or be paid less to do something you’re passionate about?
51. Do you want to have kids one day?
52. What’s your relationship to religion?
53. In relationships, are you someone who moves pretty quickly or takes things slow?
