2020 Top 100 Questions to Ask Your Potential Boyfriend/Girlfriend

Revised March 31, 2020

Ideally, going out on a date should be enjoyed by both people

Sometimes dating is casual, sometimes we date with the hope that it is the beginning of something more committed and long term.

Either way, a good date generally has good conversation, but it can be tough to think of good conversation ideas

Consider making a list of topics before the date. Write them down, read them. Try to remember some of the topics with you’re out with your date or, bring a cheat sheet😄

Here’s a list I started and have revised, several times

Consider your own answers to these questions. Remember, its possibility if you ask someone a question they would probably want to hear your answer, also

I have a few other lists on my blog. Please read🤓

I am always looking for feedback or suggestions, on this post or any others. Please post a comment

1. What would you love to be doing 5 years from now, 10 years from now?

2. What sort of future financial plans/goals do you have?
3. What is your biggest goal in life?

4. Is there an experience you’ve had that has impacted the direction of your life?
5. What is a decision you’ll make that may affect the direction of your life?

6. What is more important in life relationships or achievements?

7. Are there people you don’t like? Are there people that don’t like you?

8. Where are good places for a couple to be romantic?

9. What has been an embarrassing moment for you?
10. Do you ever find yourself bored?

11. What are good leisure activities a family should try to do together?

12. Do you think it is normal that I still might have some feelings for my Ex?

13. Do you still have feelings for an ex?

14. What do you think of this expression: Where there was fire, ashes remain.

15. Do you have a favorite book/author?
16. Describe yourself in 3 words.
17. What 3 characteristics do you see as personal weakness.

18. What are your bad/good habits?

19. How do you define hero?
20. Do you know someone you think did something heroic?

21. What would your social point of view be considered: liberal/conservative, spiritual/atheist. Have you changed your position on any current issues.

22. Do you have any opinions about politics we shouldn’t talk about?

23. What is something memorable from a first date?

24. What would the perfect life be?
25. Is there an age where being a virgin, you think, would be awkward?

26. What is your definition of emotional intimacy?
27. What’s been your most intimate experience? What it emotionally as well as physically intimate?
28. Can you have emotional intimacy without physical intimacy?
29. How long did your most intimate relationship last?
30. Do you regret any intimate experiences?

31. Have you ever had the feeling you were being watched, or being followed?

32. What was your most conflicted emotional moment?
33. Do you usually follow your heart or your head?
34. What is your opinion about same gender relationships?
35. In what ways may a past relationship positively effect a current relationship?
36. How would you react if I told you I had a relationship with a person of the same gender?

37. Do you believe in a god or gods? Can you be spiritual without religion?

38. Do you have any hobbies?

39. Have you ever experimented with legal/illegal drugs?

40. What do you think is the key to good parenting?
41. Are pets in the house okay with you? Do you like pets?
42. What is the weirdest thing about you to most people?

43. Tell me something about your first kiss.

44. If your parents don’t like me for some reason, is that a deal breaker?
45. Have you ever had a one night stand? If you did, do you regret it?
46. Do you believe in soul mates?

47. Do you have any felonies on your record?

48. What is your dream job?
49. Are you willing to move away from your family if you ever have to for a job?
50. Which living celebrity/author/singer would you like to know?
51. If you could meet a famous dead person, whom would you like to meet?

52. What do you think about unfaithfulness in a relationship?
53. Do you think love at first sight is possible?

54. If your job started negatively impacting our relationship, what would you do?
55. Do you have a favorite fictional character?
56. Do you prefer reading books or watching movies?
57. Do you have any regrets in life?
58. What is your ideal vacation?
59. Do you have a favorite movie?
60. If you are allowed to do just one thing for the rest of your life, what would it be?
61. What are some things about you that you take pride in?
62. What is the most courageous thing you have ever done in your life?
63. What is your earliest memory?
64. What do you like most about you?
65. Will you be OK with me hanging out with you and your friends?
66. If you could change something about your life, what would it be?
67. Have you ever taken dancing classes? Do you like to dance?
68. Do you think it is important to learn any form of a performing art?
69. What are you looking for in a relationship? In the long term or short term?
70. If you have three wishes, what do would you wish for?
71. Which is the song that makes you happy?
72. If you could have a superpower, what would be your superpower?
73. Who has been the most influential person for you so far in life?
74. Is there a movie that makes you cry no matter how many times you watch it?
75. If you could change one thing about yourself physically, what would it be?
76. What is the best advice you ever received?
77. What kind of music do you like?
78. Why did your last relationship end?
79. Are you still friends with that person?
80. What was a good moment in that relationship?
81. What are the craziest things that you’ve done with someone?
82. What will you have accomplished at work/school one year from now?
83. If you could go on a road trip where would you go?
84. What is the best part about family life?
85. What is a favorite memory you have of being with your family?
86. Tell me 3 good points about me.
87. What are your expectations of me in our relationship?
88. Did you ever want to kill someone?
89. Have you ever wanted something really bad and then later, not so much?
90. Is there anything I could do to make you think I am a bad person?
91. What would you do without electricity for 3 days?
92. Do you like to go shopping, not buying, just shopping, looking at stuff in stores?
93. After I had asked you out for the first time, was there any part of you that wanted to say no?
94. Where are some places you like to go on dates that might be different from where we usually go?
95. What are your views on open relationships? Do you know what an open relationship is?
96. Have you ever thought of adopting a child?
97. Is money more important to you or are relationships you share with people more important?
98. What is it that you are passionate about?
99. Do you believe long distance relationships can work?
100. What are your thoughts right now about spending the rest of your life with just one partner?

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