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150 Cute Questions to Ask Your Boyfriend

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As you begin a new relationship, it can be hard to get to know your boyfriend. You are excited and enticed by the new relationship, but it can be difficult to feel comfortable enough to really open up to your partner. For your relationship to progress, you have to open up and start to learn more about each other.

To keep your romance alive, you need to find the right cute questions to ask your boyfriend. We have compiled a list of 150 cute questions to ask your boyfriend to learn more about him and really figure out what makes him excited. Hopefully, these questions will serve as just the starting point for a lively, engaging conversation.

Fun Questions to Get Started With

1. You are given three wishes from a genie. What are they?

2. Would you prefer to have ice cream or a milkshake?

3. Let’s imagine that we are stranded on an island without any food. Would you hunt and kill animals so that we could live?

4. If you could travel anywhere at this moment, where would you want to go?



5. Do you prefer hot dogs or hamburgers?

6. If you could feed me a dessert right now, what would you choose?

7. You suddenly find five dollars on the ground. What would you do with it?

8. If you could have any type, size or flavor of cake made for you, what would it be?

9. Looking in the cupboard, you realize that there is just one cookie left. Would you share it with me?

10. Do you prefer cookies or cookie dough?

11. Do you like coffee or tea better?

12. Would you rather have me on the back of your jet ski or race me on a different on?



13. If you could be talented with music, writing or dance, what would you pick?

14. If you could ride along with you on any type of vehicle, what would it be?

15. If money didn’t matter (and you didn’t have to cook it), what would you eat for breakfast each day?

16. You are only allowed to wear one outfit for the rest of your life. What would it be?

17. If you could throw anything against the wall, what would it be?

18. What would you call your autobiography?

19. Which celebrity do you think resembles me the most?

20. If you were allowed to travel a maximum of one week back in time, what moment would you relive?

Flirty Questions to Ask Your Boyfriend

21. Would you be willing to kiss me on the neck?

22. Do you enjoy it when I touch your face?

23. What is your favorite physical aspect of me?

24. Would you be willing to hold my hand or kiss me in public?

25. If you could describe my kisses in one word, what would it be?

26. Where is your favorite place for me to kiss?

27. Do like cuddling?

28. Would you go skinny dipping with me some day?

29. Would you kiss me on my forehead?

30. Would you take a bath or shower with me?

31. Would you kiss me in a public place?

32. How many times did you think about kissing me before our first kiss?

33. Where is your favorite place to kiss me?

34. What do you think or see when you close your eyes when we kiss?

35. Would you rather give me a hug for five seconds or kiss me for one second?

36. Would you be willing to kiss me on the wrist?

37. Would you kiss me on the nose?

38. Where is your favorite place to get massaged?

39. Would you rather kiss in the rain or kiss in the dark?

Questions to Help You learn More About Your Boyfriend

40. Who knows you the best in the world?

41. Would you rather take a road trip with your friends or with me?

42. How would you describe your family members?

43. What would your ideal date be?

44. If I cooked you dinner instead of taking you to the restaurant, would that make you happier?

45. Would you be embarrassed if I called you by a pet name in front of your friends or family?

46. Am I the type of girl that you would introduce to your parents?

47. Do you have any secrets that you have not shared with me before?

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

49. Would you rather have a date to the movies or snuggle at home and watch a movie?

50. What item would I be most surprised to find in your bedroom?

51. If your friends told you to break up with me, what would you do?

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

53. Do you allow me to win games? Would you?

54. If you saw another guy trying to flirt with me, what would you do?

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

56. Is it important to you when I tell you that I love you?

57. What is your idea of a perfect date to take me on?

58. Has a movie ever made you cry?

59. Do you think that your family will like me

60. Do you talk about me with your friends? What do you say?

61. Do you like it when I tell you how attractive you are?

62. When you are alone at home, do you think about me?

63. Do you mean it when you say that you are in love with me?

64. If I made you breakfast some day, what would you want me to make?

65. Would you rather take a tropical vacation or go camping with me?

66. What is your favorite thing about traveling to new places?

67. Would you enjoy riding in a hot air balloon over the countryside?

68. Would you be willing to dress up and dance with me for no reason?

69. What signs let you know that you will become friends with someone?

70. If you did not win immediately at a carnival game, would you keep trying?

71. What is the craziest thing that you would be willing to do for me?

72. Would you rather lay on the beach with me and sunbathe or hit the water?

73. What would your dream vacation be to go on with me?

74. What do you think your best feature is?

75. Would you ever be willing to take me on a trip with your friends?

76. Do I ever do things that make you blush?

77. What is your favorite piece of clothing?

78. When was the last time that you laughed the hardest?

79. Who is your celebrity crush?

Cute Questions to Get the Conversation Going

80. Do you ever get butterflies in your stomach when you read my messages or see me?

81. What is the one quirky thing that you love the most about me?

82. What is your favorite memory of us so far?

83. Would you ever write me a poem?

84. What is your favorite pet name for me?

85. What is your favorite dream that you have had about me?

86. Have you dreamed about me ever?

87. Is there anything that you do not like about me?

88. Do you smile when you get a text message from me?

89. Would you ever stop or take a break from your favorite hobby to spend more time with me?

90. Do you think that I am cute?

91. If you could describe me in just three words, what would you say?

92. Would you write a song for me some day?

93. How would you describe my scent?

94. What is your favorite outfit for me to wear?

95. Is there something that I do that you absolutely love?

96. Would you ever take me on a picnic underneath a starry night sky?

97. If I looked differently than I do, would you still love me?

98. Do you think that I am attractive?

99. Do you think that I look cute when I am working out?

100. Does being with me make you think of having a future together?

101. What type of flower do you think describes me?

102. Do I make you feel happy?

103. Would dance with me, even if no one else was on the dance floor?

104. If I was frightened, would you hold me?

105. Do you think that I am still cute when I play sports?

106. Would you risk your life to save my life?

107. Would you give me a piggyback ride if my feet were tired or in pain?

108. Would you go with me to see a chick flick?

109. Do you think that I help you reach your highest potential?

110. If I were sad, how would you try to cheer me up?

111. If we were watching a scary movie, could I cuddle up to you and hide my eyes?

Romantic Questions

112. What adjective would you use to describe our first kiss?

113. How long do we have to date before you introduce me to your parents?

114. Is there a song that really makes you think of me?

115. What does it feel like to you when we just hold each other?

116. Do you believe in soul mates? Do you think that we are soul mates?

117. Do you still remember the day when we first met?

118. If we were to get married in the future, where would you want to go on our honeymoon?

119. How do you feel when we are not together?

120. If you think that everything happens for a reason, why do you think that we met?

121. Would you be willing to meet my parents /

122. When did you decide that we should officially be a couple?

123. Would you be willing to shout out my name to the world?

124. If I had to move far away, would you be willing to have a long distance relationship with me?

125. What was your first impression of me?

126. Do you believe in fate?

127. What was the first thing about me that made you interested?

128. If I had to move far away, would you be willing to move with me?

129. When did you first realize that you loved me?

130. Why do you like (or love) me?

131. Do you believe that love at first sight exists?

132. What is the first thing you think of when you wake up next to me in the morning?

Deep Questions to Ask Your Boyfriend

133. What would you like to change about our relationship to each other as a couple?

134. What is your biggest fear in life?

135. Have you ever fallen in love with someone before?

136. Have you ever been deeply hurt? What happened?

137. Is there something that you wish that you could change about yourself?

138. What do you want out of your relationship?

139. What is your relationship to your siblings, friends and parents like?

140. Is there something that you are afraid to tell me or talk about?

141. When do you feel like I appreciate you the most? Is there anything that I can do to make you feel more appreciated?

142. Do you have any regrets in life?

143. What was one of the best moments in your entire life?

144. Is there anything that I can help you to do?

145. What does being a couple together mean to you?

146. What is the most important thing in life to you?

147. Would you ever change something about your life if it was possible?

148. What do you like about us being a couple?

149. Is there anything more that you want to know about me?

150. What are your deal breakers in a relationship with someone?

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