1. What do you consider your best and worst qualities?
2. Have you ever had your heart broken?
3. Are you friends with any of your exes?
4. Do you believe it’s possible to maintain platonic friendships with members of the opposite sex?
5. How do you honestly feel about monogamy?
6. What’s your definition of cheating?
7. Do you have any unfulfilled sexual desires or fantasies?
9. If you won the lottery tomorrow, how would you lead your life moving forward?
10. What’s your earliest fond memory?
11. What’s the most terrifying thing that’s ever happened to you?
12. What’s your greatest fear?
13. What soothes you the most on the back of bad news or a tough day?
14. What is the best advice you’ve ever gotten?
15. Who’s the person you respect most in life, and why?
16. Who do you confide in more than anyone else?
17. Can you actually keep a secret, or is it tough for you to keep your mouth shut?
18. In what circumstances do you think it’s okay to fib?
19. Are you the type to bottle things up, overshare, or something in between?
20. What are you most passionate about in life?
21. Would you characterize yourself as someone who lives to work, works to live, or neither?
22. How would you respond if one of us was offered a job that required a lot of traveling?
23. Would you be willing to relocate for either of our jobs?
24. Would you prefer to run your own business or to work for someone else?
25. If you could design your own schedule, would you work more during the morning or at night?
26. How many hours of sleep would you say you need to function at 100 percent?
27. Are you a pet person? If so, what kind of pet do you see yourself owning?
28. How often do you like to see and/or speak to your parents, siblings, and other family members?
29. Have you ever lost someone or something you truly loved?
30. What’s your ideal climate for establishing a permanent home?
31. What’s your ideal type of vacation?
32. How do you feel about group vacations with other couples?
33. At what age do you envision yourself buying a house or owning real estate?
34. What keeps you going day to day?
35. What do you value more: careful planning or the freedom to be spontaneous?
36. Do you believe in reincarnation, or an afterlife?
37. How would you react if we had trouble getting pregnant?
38. How do you feel about adoption?
39. How many kids do you want (if any)?
40. Do you want to raise your hypothetical children religiously?
41. Would you ever stay home to parent full-time?
42. Do you expect your partner to parent full-time?
43. How do you feel about outsourcing certain responsibilities like childcare and cleaning?
44. How important are birthdays, anniversaries, and other holidays in your view?
45. How do you envision splitting holidays between your family and your significant other’s?
46. Which household chores do you most like to do?
47. What percentage of your income are you comfortable spending versus saving?
48. Do you have any outstanding debts?
49. Do you have any savings?
50. At what age do you want to retire, ideally, and where do you imagine yourself at that stage in life?