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100 Random Questions to Ask Your Boyfriend

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The best relationships are based on good communication, so it never hurts to keep the conversation going. Whether you have just started dating or have dated for years, you can easily run out of things to talk about. If this is the case, we have you covered. We have 100 random questions to ask your boyfriend. You can use these questions to get to know a new boyfriend better or find out unexpected things about a guy you have dated for months.

1. When you were growing up, what did you want to become?

2. Would you tell me if there was something stuck to my teeth or something on my face?

3. How would you describe the way that you dance?

4. A bear is charging at you. You have seconds to act. What do you do?

5. What do you think is your favorite month of the year? Why?

6. What is your favorite board game to play?



7. What weird foreign foods have you tried before?

8. Have you ever told a lie? What was it?

9. What is the best joke that you know? Can you tell me it?

10. Even if we were the only people on the dance floor, would you be willing to slow dance with me?

11. What is your favorite 80’s movie? What is your favorite B movie?

12. When you go to the movie theater, do you sneak in your own snacks or do you buy them there?

13. Do you or do you think you could ever hunt?

14. When was the last time that you danced?



15. If you could pick any Hollywood actor to play you in a movie about you, who would you choose?

16. What is your favorite Leonardo Dicaprio film?

17. How many states have you lived in? Have you ever lived in a foreign country?

18. What is your favorite video game?

19. Do you like to play pranks?

20. Which water sports are your favorites? Do you know how to swim?

21. Have you ever tried sushi?

22. What is your favorite brand of clothing to wear?

23. How would you react if you found out that one of your parents was gay?

24. Have you ever broken a bone before? What happened?

25. Would you say that you are a good cook?

26. How often do you exercise? What is your favorite type of exercise?

27. What was your favorite playground equipment to play on when you were a child?

28. What beverage do you drink in the morning?

29. Do you know how to change a diaper?

30. If you were stranded on a deserted island and could only have three books to read for the rest of your life, which books would you choose?

31. Have you ever ridden a motorcycle before?

32. Do you like insects?

33. What is your stance on women or men wearing yoga pants?

34. Have you ever gotten a speeding ticket or another type of driving ticket?

35. What is your favorite activity to do outdoors?

36. What do you like to put onto your hot dog?

37. If you were arm wrestling with your best friend, who do you think would win?

38. What is your favorite restaurant to eat at?

39. If you had a hole in your clothes, would you throw it away or fix it?

40. Would you or have you ever picked up a hitchhiker?

41. Where is your favorite place to shop at?

42. Can you do an Elvis impression?

43. How did you get along with your siblings as you were growing up?

44. Would you be alright if I paid for our dates sometimes?

45. Have you ever worn makeup?

46. Would you ever or have you ever sang karaoke?

47. Who do you think is the hottest celebrity?

48. Have you ever dressed like a girl?

49. What is your favorite Michael Jackson song?

50. Do you like to read the book before you watch the movie, or do you just skip the book and watch the movie?

51. Can you turn down a challenge?

52. Do you wear boxers or briefs?

53. Are you extremely ticklish?

54. If you were one of the characters on the Simpsons, who do you think that you would be?

55. How well do you get along with your siblings now?

56. Would you ever go on a picnic in a park or forest?

57. What is the first thing that you thought of when I said the word “Disney”?

58. Do you think that babies are cute?

59. How do you feel on rainy days?

60. How good are you at playing putt putt golf?

61. What is your favorite type of cheese to eat?

62 How are you different from your parents?

63. Which one of the Harry Potter books or movies was your favorite?

64. Would you rather have children that are all boys or all girls?

65. Do you talk to one of your parents every week, month or year?

66. What is the nerdiest thing that you have ever done?

67. What are three things that you could not live without?

68. Was your first time amazing?

69. What are the three words that you would use to describe yourself?

70. What is your least favorite word in the English language?

71. If you won $2 million, what would you do first with the money?

72. Did you think that girls had cooties when you were a small child?

73. What is the most expensive thing that you own?

74. If you could travel anywhere in the world, where would you want to go?

75. Have you ever played Magic cards?

76. When was the last time that you kissed someone?

77. I catch you on YouTube and ask what you are watching. What is it?

78. Have you ever been to Disneyland or Disney World?

79. What do you like the most about your parents? Are you like them in any way?

80. You have a free night with nothing that you have to do. What do you do during that time?

81. Do you like Buzz or Woody better?

82. What would you want your tombstone to say?

83. Do you like Taco Bell or McDonald’s better?

84. You have just opened up your own restaurant. What type of food do you serve and what do you name it?

85. Would you rather cuddle next to a roaring fire or cuddle underneath the stars?

86. What items are you willing to splurge on for yourself?

87. If you could have any super power, which one would you choose to have? Why?

88. Do you own a pair of sweat pants? What do you wear to work out in?

89. If you could change your first name to anything, what would you choose?

90. Do you like flying on airplanes?

91. Have you ever watched Survivor?

92. What is currently on your shopping list?

93. Can you name the second president of the United States?

94. Do you prefer girls to have short or long hair? What is your favorite look on a girl?

95. What is the worst present that you have ever been given?

96. What is your favorite place that you have ever traveled to?

97. If we were to have children some day, which personality trait would you want to pass down to them?

98. Do you think it is hotter to wear a little black dress or yoga pants and a t-shirt?

99. When was the last time that you ate a frozen pizza?

100. Are you still friends with your best friend from childhood?

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