January Classic Questions to Ask a Boy on your First Outing

Filed in Articles by on December 28, 2021

– Questions to ask a Boy –

 If you’ve been in a relationship with your boyfriend for a while or you just met a guy and you are looking to learn more about him to help you decide if he’s the one for you

These questions to ask a boy are really great to ask, asking lots of questions can either prove informative or annoying – so approach with caution.

Breaking the ice with a guy you like can sometimes be challenging. It can also be tough to break past the typical flirty banter and really get to know each other.

Classic Questions to Ask a Boy

Rather than just grilling him with all kinds of questions to ask a guy, try approaching him with some classic questions that will make him feel comfortable and open up a bit more.

1. What was your childhood like?

2. Did you have a close bond with your parents?

3. Do you have any brothers or sisters?

4. What was your first crush like?

5. Are you still friend with your exes?

6. If you had to describe your father, what would you tell me about him?

7. What was your biggest achievement?

8. Do you like animals?

9. What’s your favorite song from your teenage years?

10. What makes you feel happy?

11. Are you a competitive person?

12. Do you like any sports?

13. What’s your favourite book?

14. Would you lend it to me?

15. What do you think about death?

16. What about children?

17. What is your favorite memory from childhood?

18. What is your favorite scent?

19. How did you lose your virginity?

20. What’s your strongest character trait?

21. What is your weakest spot?

22. Do you consider getting married one day?

23. How do you like to dance?

24. What is your favourite album?

25. What was the worst winter of your life?

26. On a scale from 1 to 10, how good would you say you are at singing in public?

27. Are you left-wing or right-wing? Or in between?

28. Are you pro-choice or pro-life?

29. What’s the most important quality you enjoy in a friend?

30. Have you ever felt attracted to a queer person?

31. Did you ever take part in a protest?

32. Would you date two girls on the same day?

33. Would you ever date a blind person?

34. Tell me about the one who got away.

35. How many pairs of shoes do you have?

36. Do you own a suit?

37. Have you ever stalked someone?

38. What’s the biggest life lesson you have learned?

39. What’s the most significant love lesson you have learned?

40. What is your favourite summer memory?

41. What is it about us girls that makes you so horny?

42. What was the biggest letdown in your life?

43. What would you take with you on a deserted island?

44. What would you say about your relationship with God?

45. What would you change about social media?

46. What is one thing a woman can do to instantly impress you?

47. What has been your most embarrassing moment so far?

48. What is one thing a woman can do that would instantly turn you off?

49. What is your favourite compliment to receive?

50. What makes you smile even when you’ve had the worst day?

51. Would you rather own dogs or cats for the rest of your life?

52. Tell me something you’ve told no one else.

53. What was your favourite candy or treat as a kid?

54. What food would you never eat?

55. What do you think your best physical feature is?

56. What do you like the most about me?

57. If you could change your job right now, what would you be?

58. Give them three words you would use to describe yourself.

59. What does your perfect date look like?

60. What is the coolest vacation you’ve ever taken?

61. Name one country you really want to visit. “Questions to ask a Boy”

62. Would you rather go camping or clubbing?

63. What are you most afraid of?

64. What’s the nicest thing you’ve ever done for a woman?

65. What’s the nicest thing a woman has ever done for you?

66. What is your biggest dating dealbreaker?

67. What’s your earliest childhood memory?

68. What is one thing that always makes you angry?

69. What has been your greatest achievement so far?

Personal Questions to Ask a Boy

70. What is one thing you love about where you live?

71. What is one thing you hate about where you live?

72. What’s your go-to Starbucks order?

73. If you could get one gift, what would it be?

74. Do you prefer to get a gift or gift cards or money?

75. Would you describe yourself as more of an introvert or an extrovert?

76. If you could re-do one moment in your life, what would it be?

77. Where is your favorite place to go when you need to relax?

78. Do you like going to the gym or working out at home?

79. What was the last thing that made you cry?

80. What’s something a woman could do that you could never forgive her for?

81. Have you ever been betrayed by a friend?

82. What’s your favorite thing about your friends?

83. How did you meet your best friend? “Questions to ask a Boy”

84. What question do you always ask women on a first date?

85. Do you want kids?

86. What makes you want kids?

87. What’s the most trouble you’ve ever been in?

88. Would you rather holiday at the beach or in a cool city?

89. What’s your dream car?

90. What’s your favourite book?

91. What’s the worst movie you’ve ever seen?

92. Which superpower do you wish you had?

93. What’s the most fun thing you’ve ever done with your friends?

94. Are you closer to your mom or dad?

95. Who is your favourite family member?

96. What kind of extra-curricular activities did you do for fun in high school?

97. What’s your weirdest pet peeve? “Questions to ask a Boy”

98. Which is better: asking for permission or asking for forgiveness?

99. What would you do if you inherited 1 million dollars tomorrow?

100. What’s the most embarrassing moment of your life so far?

More Unique Questions

101. What fictional character do you identify with the most

102. Are you a superstitious type of person? About what?

103. Where would you rather live – a big house in the suburbs or a tiny apartment in a great location in the city?

104. If you could have any job in the world, what would it be?

105. Ever have any trouble with the law or get arrested?

106. Do you think it’s important to keep up with the news or do you not care?

107. What’s the nicest thing you’ve ever heard about yourself? What do you WANT to hear about yourself?

108. What do you want to have going on in your life in 5 years, or 10, or 15?

109. Which would you rather be, smart or happy, and why?

110. You can have one superpower – and only one. What is it, and why did you pick it?

111. What’s your biggest regret that you have in your life so far?

112. Which show on TV do you absolutely HAVE to watch live when it airs?

113. When did you have your first kiss and who was it with?

114. If you were a server, and a customer was a JERK, would you spit in their food?

115. What’s your favourite food to eat? “Questions to ask a Boy”

116. What’s the type of music do you listen to?

117. What’s the one movie you love more than any other?

118. If you could only eat one food for the rest of your life, what would it be?

119. What’s the funniest thing that’s ever happened to you?

120. Has anyone ever walked in on you naked?

121. How do you deal with people in your life that you don’t like?

122. What’s the funniest thing that happened in your childhood?

123. Do you like waking up early or staying up late?

124. What are you most afraid of?

125. What actor would play you in a movie about your life?

126. Guess – what am I thinking about right now? “Questions to ask a Boy”

127.  If you had to give me a nickname right now on the spot, what would it be?

128. Do you think it’s possible that we met in a previous life?

129. Pick one to live in: beach, city, or country?

130. How would you describe me to someone who doesn’t know me?

131. Which describes your personality… naughty or nice?

132. What’s the sexiest animal in the animal kingdom?

133. Who’s a celebrity you have a crush on?

134. You get to date one celebrity – who is it?

135. If you had the power to read someone’s mind, whose would it be?

136. What would you do in a week if you were told you only had a week to live?

137. Did you ever cheat on a test in school?

138. Do you feel like something is missing from your life?

139. What are you most passionate about?

140. What is one thing you’d love to learn more about?

141. What is your favourite non-physical part about yourself?

142. What is more important to you: money or happiness?

143. What was the last thing to make you cry?

144. What is your biggest fear?

145. What is the craziest thing you’ve ever done?

146. What is your biggest pet peeve?

These questions will open the gates to a deeper connection and bond, something so many people struggle within this day and age. So enjoy the list, jot down your favourites, and have fun going through them with a guy you like.

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CSN Team.

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