Skip to Content

150 Deep Personal Questions To Ask A Guy To Create Intimacy

A photo of Tom who is the Co-Founder of Questions About Everything

To learn how this content was created please read our Editorial Guidelines.

If you’re looking to get to know someone it can be tricky if you’re asking standard questions everyone always asks.

These personal questions to ask a guy are designed to help create a more intimate connection and get to know them on a much broader and deeper scale.

We have a wide variety of topics below that you can use to choose the right question for the guy in your life. Relationships, sex, politics, they’re all covered below.

Our collection of deep personal questions to ask a guy are perfect for getting to know someone you’ve just met as well as getting to know a guy you’ve known for a while, or your partner better too!

Personal Questions To Ask A Guy List

We have selected a variety of questions and topics all with the singular goal of getting to know the guy in your life on a deeper level.

Some of them may come across as too personal. But as with our weird questions to ask a guy, if you know who you’re asking them to beforehand you can select the most appropriate ones.

1. Are you someone who is looking for a long-term relationship or a one night stand?

personal questions to ask a guy long term relationship or one night stand

2. Do you think both parents should work or should the women stay at home while the man earns money?

3. Do you want children? If so, what age would you like to have them, and how many would you like?

4. Do you think men and women are equal in society and is it possible they ever will be?

5. What are your thoughts on men that become stay-at-home dads?

6. Is the career you’re doing now something you can see yourself doing for years to come, or is it a temporary job?

7. What behaviors do you consider to be a red flag when you’re dating someone?

8. How important is keeping close to family for you? Do you often attend family events, or do you make excuses to miss them?

9. Do you think someone’s looks are more important than their personality?

10. Do you think it’s healthy to spend time apart when you are in a relationship?

You might also like:

11. What’s one trait that instantly turns you off from a person?

12. How religious are your family? Did it affect you and your outlook on life? Do you still follow the same religion now?

13. Is it necessary to you that your partner has the same interests and hobbies as you?

14. Would you like to be in a relationship with someone who’s very religious?

15. What’s the most embarrassing thing you’ve done for love?

16. Do you think you would be able to cope if you had to bring up a child by yourself?

17. What are your thoughts on online dating sites, like Tinder and Bumble? Do you think they are safe, and can you meet your soul mate on them?

18. Do you think same-sex couples should be able to adopt?

personal questions to ask a guy same sex adoption

You might also like: Questions to ask your crush

19. What one thing would you like your parents to know, that you haven’t told them?

20. What’s the biggest lie you’ve told someone? Were you caught out?

21. Have you ever been attracted to any of your sibling’s partners?

22. Do you think it’s essential to live near to your family when you start your own?

23. Would it be ok if your child brought someone home who was of a different race or religion?

24. How would you react if your parents told you that you were adopted?

25. How would you propose to your future wife/husband?

26. Do you think men need to open up more about their mental health?

27. Would you say you’re good at knowing what your partner wants?

28. If you inherited a large sum of money, how would you spend it?

29. Who was your role model growing up?

30. What are your thoughts on relationships? Have you been in one before? Do you have any fears?

31. How often did you get in trouble as a child? What was the worst situation you got in?

32. Have you ever been caught doing anything illegal?

33. Have you ever been arrested? What were you charged with?

34. What are your biggest regrets?

35. Are you able to trust people easily?

36. Have you stayed in a county jail for more than one night?

personal questions to ask a guy been into a county jail

You might also like: Questions for your boyfriend

37. What are your strength and weaknesses?

38. What’s the craziest thing you’ve done to get people’s attention?

39. How does someone know that you want some time alone?

40. When you get angry at something, what do you usually like to do to calm down?

41. Have you ever broken someone’s heart on purpose? How did you feel about it at the time, and what do you think about it now?

42. Are you a naughty person?

43. What’s been the best movie you’ve watched recently?

44. Do you think lower-income families should pay taxes?

45. Are you into the ’60s, 70’s and 80s genres of music? If so, what’s your favorite song?

46. Were you closer to your mom or dad growing up?

47. Do you ever find yourself getting jealous of your siblings?

48. Do you think taxing people is the right thing to do?

49. If you could add anything to your life right now, what would it be?

50. How old were you when you realized your family was more important than your career?

51. What’s the most romantic thing someone has ever done for you?

52. What’s the most romantic thing you’ve done for someone?

53. Do you find it hard to say sorry?

54. Do you find it hard to forgive people even if they say sorry?

personal questions to ask a guy finding it hard to say sorry

Next: Flirty questions to ask your crush

55. What’s the most amount of money you’ve spent on something?

56. Have you ever regretted spending a lot of money on something?

57. What positive change have you recently brought to your life?

58. Have you ever suffered from anger issues? Have you ever got angry at something small and insignificant?

59. As a child, what was your favorite toy, video game or cartoon?

60. Did you collect anything as a child?

61. What recent memory do you cherish the most?

62. What did your dream girl look like growing up?

63. Have your behaviors and habits changed over time?

64. Did you have more male or female friends growing up?

65. Did you have any experience of bullying growing up?

66. Have you been a victim of a crime?

67. Are your parents still married?

68. Are your parents still alive?

69. What insecurities did you have as a teenager?

70. Do you have any stepbrothers or sisters?

71. Do you know your father? If not have you ever tried to make contact with him?

72. What age were you when you lost your virginity?

personal questions to ask a guy age when you lost your virginity

You might also like: Online dating questions

73. What age were you when you had your first kiss?

74. Do you think only the wealthy should pay taxes?

75. Who was your most influential teacher or professor? Why did you admire them?

76. What quality makes you the person you are?

77. Do you have any secrets that you haven’t told me?

78. What do you find unattractive in people?

79. What hobby would you like to try if money and time were no issue?

80. What highly anticipated movie did you not like?

81. Do you think you will settle down with someone one day?

82. Have you ever suffered from depression? How did you overcome it?

83. Have you ever pretended to be someone you’re not?

84. Do you consider yourself more important than most people?

85. What type of wedding would you like?

86. Would you prefer to live in the city or the countryside?

87. Is getting married important to you?

88. What age would you like to retire?

89. What would you like to do in your retirement?

90. How much money would you need to live when retired?

Next: Questions to ask a guy to know his intentions

91. What country would you like to retire to?

92. Have you ever questioned your sexuality?

93. Would you mind if your child said they were gay?

94. What about life sickens you most?

95. Do you ever worry about how and when you will die?

96. Do you think that you will be together with loved ones after you die?

97. Would you try to dictate what your child/children did with their life?

98. Would you want your child/children to work to contribute to the household bills as soon as possible?

99. What age would you let your child/children live with you until?

100. Would you ever consider moving back in with your parents if things got tough?

101. Have you ever found yourself in financial difficulty?

102. Have you ever declared yourself bankrupt?

103. Have you ever taken out a loan or credit card?

104. What steps do you take to manage stress?

105. What’s your view on wars starting due to different religious beliefs?

106. What traits do you look for in someone?

107. Do you prefer to avoid conflict or run toward it?

108. Are you someone that can compromise, or does it always have to be your way?

personal questions to ask a guy making a compromise

You might also like: Random questions to ask a guy

109. Do other people affect your opinions and thoughts?

110. Would you like me to give you more space or more support?

111. Have you ever been in a life-and-death situation?

112. Do you have any habits that have stopped you from meeting new people?

113. Do you feel comfortable in your body?

114. What would you change about your body if you could?

115. Have you ever said something to get a reaction out of someone intentionally? How did you feel after it?

116. Do you think you’re a flirty or shy person?

117. What do you enjoy most about intimacy?

118. Why are men so cautious about talking about their mental health?

119. Have you ever been to counseling?

120. Have you ever been to confession?

121. Have you had post-traumatic stress disorder?

122. Are you persistent when you want something?

123. Do you give up on things easily when times get tough?

124. Do you enjoy watching/looking at pornography?

125. Would you ever attend a strip club?

126. Do you ever think about your ex?

personal questions to ask a guy thinking about your ex

Next: Questions girls are afraid to ask guys

127. Do you ever picture your current partner making love to someone else?

128. What’s your opinion on sex workers?

129. What are you looking forward to this year?

130. What’s going to be your new year’s resolution?

131. What are you scared tomorrow will bring?

132. What are the little things in life that always make you smile?

133. Who inspires you most in your life right now?

134. Have you ever lost money on an investment?

135. What activity do you like doing alone?

136. Do you need to be constantly reassured that the work you’re doing is correct, or are you able to work on your initiative?

137. Are you a touchy person?

138. What are your opinions on people that have foul body odor?

139. Do you have any sexual fantasies?

140. What is the best compliment you’ve received from someone?

141. Do you feel grateful for your life so far? How do you show gratitude?

142. What’s your signature dance move?

143. How would you usually make the first move on a date?

144. Do you ever dance in front of the bathroom mirror?

145. Is there a movie/book you’re embarrassed to say you like?

146. What superpower would you like to have and why?

147. What would you be most like to protest about?

148. Would you change to a plant-based diet if it meant saving the world?

149. Are you a butt or boob man?

150. What would you want it to be and why if you woke up with a skill or talent?

Looking For More Questions?

Dirty questions to ask a guy – If you want the conversation to get a little spicier, these are the questions you should ask.

Dirty questions to ask your boyfriend – If you have a boyfriend, these questions are guaranteed to get him in the mood!

Funny questions to ask a guy – Lighten the mood between the two of you with these fun questions!

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.