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BEST 100 Questions to Ask on your First Few Dates posted Feb 10, 2018

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If you want to have the best date ever, then consider asking your date questions that will ensure that you get another chance at it. The response might even help you know if you want another date with the person.  Not all questions will apply so read the list then pick the ones that fit for you. Remember, these are questions that you might ask your date while you are sharing time with him/her on the first few dates. Here we go.

1. How are you liking this event?

2. How was your day?

3. Do you have a signature dish that you prepare?

4. What’s the last TV show that you binged watched?

5. What’s your favorite TV show?

6. Where are you from?

7. Where is a place that you hope to travel one day?

8. Who was your role model growing up?

9. Do you kiss on the first date?

10. How would someone know that you really like them?

11. Are you hoping to make a match tonight?

12. Do you find ________ awkward?

13. Are you looking for love or fun?

14. Would you consider yourself emotionally available?

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

16. What is your biggest attraction to a person?

17. How long has it been since your last relationship?

18. Have you ever done anything like this before?

19. Have you tried online dating?

20. Have you had any luck with online dating?

21. What would you say is the best place to meet someone?

22. How would you describe your ideal date?

23. Do you think you would do something like this again?

24. What’s something you do not like to tell people on the first date?

25. Do you believe in love at first sight?

26. How do you know when you really like someone?

27. What do you think about Ann Marie’s (Title of your choice) book?

28. What are you drinking?

29. What is your favorite kind of music?

30. What do you do professionally?

31. Who are you more like, your mom or dad?

32. What are you doing after this?

33. How many siblings do you have?

34. Do you have a celebrity crush?

35. Where would you like our first date to be?

36. How long have you been single?

37. Do you believe men and women can be platonic friends?

38. Are you happy in your life right now?

39. Do you think you are good or bad with relationships?

40. What are your pet peeves?

41. Are you more into sports or art?

42. In 10 years, where do you see your life?

43. Do you like living in (the State you're in)?

44. Do you have any nicknames?

45. Tell me about your best friend. What qualities do you like or dislike about them?

46. What goal is the most important for you to achieve in your lifetime?

47. Have you ever been married?

48. What are you most passionate about?

49. What would your best friend tell me about you?

50. What would your last partner tell me about you?

51. What would your co-workers tell me about you?

52. If money were not an issue, where would you travel?

53. How good are you at controlling your temper?

54. How often do you exercise your mind?

55. How often do you exercise your body?

56. What is it that you love about yourself?

57. Give me one adjective to describe your family.

58. Do you think you know your purpose in life?

59. If you could have a superpower, what would it be?

60. What’s your purpose of dating at this time in your life?

61. What’s your favorite holiday?

62. Do you have any roommates?

63. What was the last book you read?

64. What are your romantic goals at this time?

65. Do you believe in God?

66. Who is someone you admire the most and why?

67. How did your last relationship end?

68. Tupac or Biggie? Miles or Coltrane? (Choose your preferred comparisons for the next 5-questions)

69. Patti Labelle or Anita Baker? 

70. Rihanna or Beyonce?

71. Common or Wyclef?

72. Nikki Minaj or Cardi B?

73. Garnett Silk or Beres Hammond?

74. How many continents have you visited?

75. Are you the oldest, youngest, middle child, or only child?

76. If you could run your own business, what would it be?

77. Would you describe yourself as affectionate?

78. Would you describe yourself as ambitious?

79. Would you describe yourself as content?

80. What do you do for fun?

81. Where did you go to school? High School? College? Training?

82. How do you wind down from your day?

83. Do you travel a lot?

84. What is the longest period of time that you have been single?

85. What do you expect on a first date?

86. What have you found to be the reasons for any break-ups in your life?

87. Do you like your job?

88. Are you nervous?

89. Do you believe in gender roles?

90. Would your family be surprised that you are at an event like this?

91. What kinds of things make you laugh?

92. Where is your favorite place in the entire world?

93. What is your favorite movie?

94. How do you spend most of your weekends?

95. What were you like as a kid?

96. What should I know about you that I would never think to ask?

97. Have you figured out your calling in life?

98. What do you hate most about the dating process?

99. What are your non-negotiables?

100. Do you have any pets?

Note: Be prepared for "both" in response to "either-or" questions.

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