Mental Health

100 Dirty Questions to Ask Your Boyfriend

You love your boyfriend, but it would be impossible to know everything about him . . . or is it? With the right conversations, you can get him to open up and learn more about him. While it would take years to learn everything about him, you could at least learn about what he likes in the bedroom. These 100 dirty questions to ask your boyfriend are perfect for finding out what he likes. If you haven’t already enjoyed some time in the bedroom together, these questions can also hint that you would like to move in that direction.

Flirty Questions to Warm Up With

1. If you could dress me in anything for a special date, what would you have me hair?

2. Do you like long or short hair better?

3. Do you prefer thongs, boy shorts or a different type of garment?

4. I am completely stressed out one day when I get home from work. What do you do to help me relax?

5. What is your favorite part of my body?

6. Would you like it if I made the first move?

7. If I asked you to give me a full body massage, where would you start on my body?

8. When do you think that I am the most beautiful?

9. Do you ever feel jealous when you spot other guys checking me out?

10. Is there one thing that I could do to be more irresistible to you?

11. Do you like it when I am jealous or possessive about you?

12. Are you good at dirty talk? Could you give me an example?

13. If you could see me wearing anything, what would you want me to wear (or not wear)?

14. Would you ever make me breakfast in bed?

15. Did you think that it was love at first sight when we met? Do you think that love at first sight exists?

16. Do you think it is more attractive when I wear a flirty dress or tight jeans?

17. Would you rather me wear lingerie or nothing at all?

18. Have you ever bragged about me to your friends?

19. What makes you turned on the most?

20. If you could describe my body using just three words, what would you say?

21. Would you prefer me to wear a black or white lace t-shirt?

22. Imagine that I just caught you staring at me. Where were you staring at?

23. What is your favorite thing for me to do to you in bed?

24. Have you ever wanted to tear my clothes off?

Sexy Questions to Ask Your Boyfriend

25. Do you like making out?

26. How often do you actually think about having sex?

27. What is your favorite position?

28. What part of your body is your favorite place to be massaged?

29. Do you feel more sexually aroused in the morning or at night?

30. Do you prefer girls who have large breasts or a large bottom?

31. Have you ever gone to a strip club?

32. What type of music do you think is most enticing in the bedroom?

33. What is the weirdest place that you have ever had sex?

34. If you could only use three words, how would you describe your package?

35. Do you prefer to be on top or bottom?

36. Do you like to have dirty talk on the phone, texts or Facetime?

37. Have you ever had a one night stand before?

38. Have you ever had sex in a movie theater?

39. Do you sleep naked, in briefs or in boxers at night?

40. Have you ever had sex in the backseat of a car?

41. Do you enjoy experimenting with new positions?

42. If you were looking for a movie to watch online, what would you look for?

43. When you wake up next to me in the morning, what is the first thing that you think about?

44. Is it okay to laugh in the bedroom or would you rather that we always keep things serious?

45. Have you ever named your package? If not, what would you name it?

46. What do you do when you are watching a movie with your parents or family members and a sex scene comes on the screen?

47. Do you ever have fantasies about me? What are they?

48. Have you ever gone skinny dipping? Were you alone or with other people?

49. How old were you when you lost your virginity?

50. What object (such as a banana) did your sex ed teacher use to show you how to use a condom?

51. How many girlfriends have you had? How many of them were serious relationships?

52. Do you think that you would be on Santa’s naughty or nice list?

53. What is your opinion on open relationships?

54. What did you do to try to get me interested in you? What techniques worked the most?

55. Did your parents ever have the “talk” with you?

56. Which part of your body is your favorite?

57. Have you ever had a dream about me? What happened in it?

58. Do you think that you are a romantic person?

59. Do you have a name for your package?

60. Do you prefer to have sex with the lights on or off?

61. How many of your exes’ numbers are still in your phone?

62. What is your number one turn off in a partner?

63. If you had to choose, would you say that you are Thor, the Hulk or Captain America in bed?

64. Do you ever have naught sexual dreams?

65. How old were you when you had your first kiss?

66. Do you find it exciting to be sneaky or have sex in unusual places?

67. Has anyone ever seen you naked on accident? Have you ever accidentally seen someone else naked?

68. Did you ever have fantasies about me before we started dating?

69. What do you think about hickies?

70. What did your first sexual partners say that you were like in bed?

71. Do you like cuddling up together?

72. What is the longest that you have gone without sex?

73. What is the hottest thing that you have ever done to someone else?

74. What was your first “adult” experience?

75. Do you own any toys that you want to use?

76. What is your favorite position when you are with me?

77. What do you think that you are best at sexually?

78. Have you ever had sex outside?

79. Have you ever had a crush on your teacher?

80. How many single girls’ phone numbers are in your phone right now?

81. How often do you like to have sex?

82. What is the craziest thing that you have ever done?

83. Describe your ideal date to me.

84. What is something new that you would like to try in bed that we have not done?

85. What is the most public place that you have touched yourself?

86. What is your favorite turn on?

87. Do you like it when I talk dirty to you?

88. What is the best experience that you have ever had in a bedroom?

89. What is the most number of times that you have had sex in a row?

90. Have you ever taken naked pictures of yourself? Have you ever received naked pictures of someone else?

91. Do you like to watch me touch myself?

92. Do you enjoy going down on me?

93. Do you like it when I send you naughty pictures?

94. Have you ever had sexual thoughts about someone of the same gender?

95. Have you ever been cheated on or cheated on someone?

96. Do you like having your hair pulled during intimate moments?

97. Have you ever been caught touching yourself by someone?

98. If you could describe your love making like a weather event or natural disaster, what would you call it?

99. What do you think is the most attractive in a girl?

100. How many rounds do you think you could go now? What about on your wedding night?