Questions To Ask To Gauge Compatibility With Your Prospective Partner     

  1. Who do you most admire, and why?

  2. Did you enjoy your childhood?

  3. If you had a million dollars to give to a charity, which charity would the money go to?

  4. Do you think men and women are equals?

  5. What is your biggest fear?

  6. What makes you angry?

  7. What do you need to feel fulfilled in life?

  8. Do you think people are more influenced by their environment or by their biological traits?

  9. What do you think your purpose is?

  10. Who is the villain in your life story?

  11. What words do you think people use to describe you?

  12. What words do you want people to use to describe you?

  13. If you could change one thing about yourself, what would it be?

  14. When was the last time you cried?

  15. Do you think Younger You would be happy with what you have become?

  16. What is the best way I can be a supportive partner to you?

  17. What has been your greatest accomplishment in life thus far?

  18. What has been the happiest moment of your life up until now?

  19. Are there things I say or do that make you want to spend less time with me?

  20. For what do you want to be remembered?

  21. How can I make you feel more appreciated and honored?

  22. What do you think we can do to make our relationship stronger?

  23. Do you think we are all at the mercy of fate?

  24. When do you feel most loved?

  25. If I could live your life for one day, what do you think would surprise me the most?

  26. How did your last relationship end?

  27. Are you and your ex still friends?

  28. How many sexual partners have you had?

  29. Have you been tested for STDs/HIV?

  30. Would you be willing to go in for testing again before we get more involved?

  31. How would you handle it if you thought another guy/girl was hitting on me?

  32. How do you cope with stress?

  33. Do you have any bad habits I should know about?

  34. What's the worst thing you've ever done?

  35. Are you able to keep your anger under control?

  36. Have you ever broken the law?

  37. How would you handle it if you lost your job?

  38. Do you like to travel or would you rather stay home?

  39. How do you handle disagreements?

  40. Do you think men and women can be platonic friends?

  41. Do you think it's OK for men and women who are in separate relationships to go have coffee or lunch together?

  42. What is something you do which might cause me to question your loyalty?

  43. What are some of your ideas for how to keep a relationship strong over time?

  44. What do you think of my dream of becoming a ______? (Fill in your own goal, like novelist, karaoke star, or TV personality.)

  45. Do you think it's OK for people to vent to others about their significant others, or do you think that it's completely disrespectful and complaints should be kept within the relationship?

  46. When you break up with someone, how do you do it?

  47. What's the worst breakup you've ever experienced? Why was it so bad?

  48. What are your thoughts on marriage?

  49. What are your thoughts on divorce?

  50. What do you consider cheating, besides the obvious?

  51. Are you comfortable talking about where our relationship is going?

  52. If one of my friends flirted with you, would you tell me?

  53. If one of your friends or family members told you to break up with me because he/she didn't like me, would you?

  54. How do you feel about my family and/or friends?

  55. How would you deal with a disagreement with one of my family members or friends?

  56. How much time do you think we should each spend with our family/friends outside of gatherings that require us both to be there?

  57. What do you tell your friends about me when I'm not around?

  58. If one of your friends flirted with me and I told you about it, how would you handle it?

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