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100 Questions to Ask on a Date

Updated on July 27, 2008

100 Questions to Ask on a Date

The first, second and even third dates can be awkward. Do you find yourself stuck in uncomfortable silences wondering what to say next? Once you find out a little bit of background about your date, where do you go next? What questions are too personal at this stage in the game? I've complied a list of 100 ice-breaking questions to ask on a date. Of course you don't want to try to cram in all 100 of these questions, or even 50 for that matter. Where the conversation goes is dependant on your date's specific background, career and lifestyle. So pick and choose carefully. You should only need to a few of these in your back pocket to really get a conversation going. Good luck!

Questions

1. What was your best job?

2. What were your worst jobs?

3. Tell me all the places you worked

4. Tell me about your best friend

5. Tell me about your family

6. Tell me about your relatives

7. What was your first car?

8. Favorite movie star?

9. Favorite entertainer?

10. Favorite song?

11. What were your life changing moments?

12. First girlfriend/boyfriend?

13. First kiss?

14. What is the dumbest thing you have ever done?

15. Have you ever been arrested?

16. Political affiliation?

17. Have you voted for someone you wished you hadn't?

18. Have you used drugs?

19. Do you like to shop?

20. Best way to relax?

21. Favorite thing to do alone?

22. Ever had a one night stand?

23. Do you save money?

24. What hobbies to you spend money on?

25. If you found a $100 what would you do?

26. Do you want children/more children?

27. Are you a good parent?

28. What makes a good parent?

29. Are you romantic?

30. Ever loose a pet?

31. Dog or cat?

32. Pets growing up?

33. Sleep in the nude?

34. Favorite midnight snack?

35. Do you exercise?

36. Did you ever see your parents making love?

37. Peanut butter and what?

38. What is one food you will never give up?

39. What is a food you can live without?

40. Favorite drink?

41. Perfect day?

42. How many cds do you own?

43. How many dvds to you own?

44. Favorite thing to spend money on?

45. What is the weirdest thing about you?

46. What is on your bedside table?

47. Are you cheap or thrifty?

48. Ever been in love with 2 people at the same time?

49. Grades in high school?

50. Favorite teacher and why?

51. Relatives in jail?

52. Toppings on pizza?

53. Black or white?

54. Glass half full or half empty?

55. Ever been to a food shelf?

56. Ever milked a cow?

57. Ever tipped a cow?

58. Bath or shower?

59. Mountains or the beach?

60. Plane, train or automobile?

61. Favorite all time movie?

62. Worse movie you have ever seen?

63. Best concert you have been to?

64. Beer, wine or coffee?

65. Best vacation?

66. If you could retire tomorrow what would you do?

67. Worse vacation?

68. Three places you would love to visit?

69. Worse boss?

70. If you could do anything what would it be?

71. Super powers you wish you had?

72. Ever had a massage?

73. Ideal romantic dinner?

74. Dumbest purchase you ever made?

75. Where did you find money when you were flat broke?

76. Ever sold blood?

77. What sporting event/concert/entertainment would you buy tickets to regardless of price?

78. Ever hit a jackpot on a slot machine?

79. Ever won the lottery?

80. What would you do with your lottery winnings?

81. Are you a neat freak?

82. Can't stand being around people who_________?

83. Crowds or small groups?

84. How old do you want to live to?

85. Loose your sight or hearing?

86. Ever had a crush on a member of the same sex?

87. Pet peeves?

88. Most annoying habit?

89. Sexiest parts of a member of the opposite sex?

90. Major turn offs?

91. Tattoos?

93. Piercings?

94. Plastic surgery--would you/have you?

95. Computer geek?

96. Trekee?

97. Play an instrument?

98. Been in a band?

99. Most embarrassing moment?

100. Nude beach yes or no?

What was your question on your first date?

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      anonymous 4 years ago

      Good luck with #51

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