When dating someone new, heck, or even wanting to get to know your current partner on a deeper level, consider these questions for conversationalizing. Truly listen to their answers, their stories, their tones as they talk through what comes up. Genuinely ask the question from a place of humble love and accepting curiosity, then do what most people need the most: LISTEN. Focus on their words and language, not on what your rebuttal or next thing to say will be. Here goes:

1. What is your relationship like with your family?

2. Who are your best friends?

3. What do you love about them?

4. Tell me about your holiday traditions?

5. Who is your favorite band, and why? What do they mean to your life?

6. If you have no plans for an entire weekend, how do you spend your time?

7. What's your favorite thing to do when you travel?

8. Which way does the toilet paper roll go on? (Broader question: What are you particular about? Not particular about?)

9. A friend calls and says they're stopping by in 5 minutes, what do you do between the notification and the time they arrive?

10. What are your favorite scents? What feelings and memories do those bring up for you?

11. How do you keep yourself organized?

12. A family member gets into an unfortunate situation that you don't agree with, what do you do?

13. You have a 6 AM flight, how do you prepare, what do you wear, what's your morning like, etc?

14. What are your favorite movies?

15. How do you celebrate others?

16. What's your most prominent childhood memory & how does it impact you today?

17. Do you prefer to hold the door for others or to have the door held for you?

18. What's your go-to outfit?

19. What's your favorite Adele song?

20. How do you deal with loss? View loss?

21. How do you handle changes?

22. To hand wash the dishes or to toss everything in the dishwasher?

23. What traditions have you developed as an adult? 

24. What did you learn in your teenage years?

25. What lessons from your twenties do you appreciate the most? 

26. Who is your favorite teacher and what do you miss/appreciate most of them?

27. How often do you clean your home and have clean sheet day?

28. What do you do to pamper yourself?

29. What's your dream job/career/business?

30. Describe your current lifestyle? And your ideal lifestyle? How do you get from here to there?

31. What are your turn-ons? Turn-offs?

32. When and how do you feel most yourself? 

33. Where and how do you feel most at home? 

34. How do you take your coffee?

35. Do you enjoy mornings? 

36. Who, and what are the most important & prominent themes in your life?

37. Who are your favorite celebrities and what do you admire about them?

38. What do you do to improve the lives of others?

39. Do you meditate/pray? 

40. Describe your idea realtionship

41. You're going on a surprise trip & don't know the location or how long you'll be away. What do you do?

42. You have plans to meet a friend for coffee, you get there early. Or late? They call to say they'll be an hour late, what do you do now? How do you react and spend the time waiting?

43. Why do you think/feel we are here?

44. Tell me your favorite story

45. Do you have siblings? What are your relationships with them?

46. What have you learned from past break-ups?

47. What's your favorite meal, and why?

48. You can change one thing in your life right now - what is it and why?

49. What's your favorite dessert? Least favorite?

50. What's your beverage of choice in various settings: weddings, dinner, breakfast, lunch, out with friends, traveling, etc?

51. How do you work through challenges & problems?

52. You can't go to sleep until _____ ?

53. You need an outfit for something at the last minute, where do you go?

54. What's been the most pivotal moment in your life?

55. Are you spiritual, religious or both?

56. What's your favorite car, and why? Dream car? Why?

57. What's your favorite subject/topic to learn about? 

58. You're packing for a picnic, what do you pack?

59. What's your favorite material possession(s)?

60. What is your relationship and attitude with money?

61. How do you feel about and what do you think about marriage? What are your beliefs? 

62. What's your gun stance? Abortion? Politics? Immigration? 

63. We need to go to my hometown for a weekend, how do you feel about it? (population 1000. very conservative. lots of family time. guns. churches. country.)

64. We are going to spend a weekend with your family - what's it like? Where are we going, what do we do? How do we get there? Are you excited or reluctant?

65. You're always hot and I am usually cold. How do we compromise on comfort?

66. How is your self esteem developed? 

67. Do you consider yourself to be a good listener? Observant? 

 

As with everything, this list is a living, breathing document that's always up for a change as more questions come up. Add your own. Remove the ones that don't feel right. Put your own twist on them. It's not truly the question that is important, it's the outcome: getting to know another person and determining compatibility. 

Live good, live well.