100 Questions to Ask A Girl–From An Upscale Matchmaker

Coming up with the right questions to ask a girlfriend is not always easy. If you are unsure about what the right questions to ask a woman you are dating are, then keep reading. Really, if you are a good conversationalist, you can ask just about anything that you want as long as it is in the right context. But, you may be struggling to come up with things to say to your girlfriend or a woman you are dating and you might need a little help.

This is by no means a definitive list of all of the things that you can ask a woman, but it may help you get started. After all, questions can usually lead the conversation into interesting places, so you don’t want to feel like you are stuck wondering what things to say to a woman are.

Here are 100 quick questions to ask your girlfriend that can get the conversation flowing with her:

1. How was your day?

2. Who is your best friend?

3. Why is that person your best friend?

4. What’s your favorite band?

5. Why are they your favorite band?

6. What is the best kind of music in the world to you?

7. What was your favorite concert you ever went to?

8. Why was that your favorite concert? What happened there?

9. What would be your PERFECT day?

10. What would you do on your perfect day?

11. Who would you be with on that day and why that person?

12. Do you like sushi?

13. Do you agree that men are hard to understand?

14. Do blondes really have more fun?

15. Have you ever dyed your hair?

16. Would you ever dye your hair?

17. Would you ever get a tattoo?

18. What would you get a tattoo of and why that tattoo?

19. Do you like coffee?

20. What was the worst class you ever took in school?

21. What was the best class you ever took in school?

22. Have you ever had a pet?

23. Do you like animals?

24. What is your favorite animal and why that animal?

25. Do you know how to drive a stick shift?

26. What was the best date you ever went on like?

27. What was the WORST date you ever went on like?

28. When did you have your first kiss?

29. Do you like your job/career?

30. Why did you choose that job./career?

31. Do you like to play video games?

32. Do you like guys who play video games?

33. Are sports something that you like to do?

34. What sport is your absolute favorite?

35. What sport is the most boring in the whole world to you?

36. How many pairs of shoes do you own?

37. Are you one of those girls who is addicted to shoes?

38. What’s the first word that comes to mind when you hear the word, dating?

39. If you could travel anywhere in the world and spend a week there, where would it be?

40. Why would pick that place, is there any special reason?

41. Have you ever been to a foreign country?

42. Do you like traveling?

43. Why is the Jersey Shore such a hit?

44. Do you watch a lot of television?

45. What is the best show on television in your eyes?

46. If you could never watch television again, would you freak out?

47. Did you go to your high school prom?

48. Did you like the guy you went to the prom with?

49. If you could do it all over again, would that guy you went to the prom with be your first choice?

50. What was your first day of college like?

51. Did you do more partying or studying in college?

52. Ever have a crush on one of your professors?

53. Have you ever broken a guy’s heart?

54. Have you ever competed with a friend for a guy?

55. Has a guy ever come between you and one of your friends?

56. Do you still watch cartoons ever?

57. If you do, what cartoon is it and why?

58. Have you ever lied to your parents about something?

59. How long do you have to be dating a guy to introduce him to your family?

60. Have you ever kissed another girl?

61. What was the was the worst job that you ever had to do?

62. Were you popular in high school?

63. Do you still hang out with the same friends from high school or college?

64. Have you ever had sex in public?

65. Have you ever made out in public?

66. Did you ever get caught fooling around with someone?

67. Is cheating okay?

68. Has anyone ever broken your heart?

69. Have you ever been cheated on?

70. What is your favorite subject to read up on?

71. If you had to choose between television and books, what would you choose, honestly?

72. What is the stupidest thing you ever spent money on?

73. Do you know how to cook?

74. What would you cook for me and why?

75. Do you like guys who know how to cook?

76. What was your funniest summer camp experience?

77. Were you a geek in the band? Don’t lie…

78. Would you date a guy who was in a band?

79. What do you think about ‘open’ relationships?

80. Is the 3 day rule to call a woman, silly or the right thing?

81. How many dates does it take for you to know that you really like a guy?

82. What would your friends say is your BEST quality?

83. What would your friends say is your WORST quality?

84. Do you like lazy Sundays?

85. Which is better, hot or cold weather?

86. Do you know how to ski or ice skate?

87. What would be the most romantic thing a guy can do for a woman?

88. Do you think that love stinks?

89. Are you a closet computer geek?

90. Would you say that you were a typical woman?

91. Did you ever like ‘boy bands’ like N’Sync?

92. Do you like clubs or bars or neither?

93. What is the longest you have gone without sex?

94. Which is better, Spring or Fall?

95. What do you prefer, beer or wine?

96. Would you ever call in sick to work to just go out and have fun?

97. How do you like to be kissed?

98. What is your favorite place to be touched?

99. Have you ever had a crush on a woman?

100. Do I ask too many questions?

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