150 Deep, Personal Questions to Ask a Guy to Create an Emotional Connection

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Guys are known to be less emotional than girls which can make them hard to connect to.

Let’s change that and dive deep into the minds of men by asking these 150 deep questions.

Table of Contents

1. What is your life philosophy?

How does he feel about life… is it all we have?

2. How did your parents raise you?

Were they strict, did they teach him a lot of lessons on how to be or did they try to be his best friend and let everything slide?

deep questions can make a guy love you even more

3. What keeps you up at night when you can’t fall asleep?

Does his mind spin or is he pretty at ease and a deep sleeper?

4. How did you learn how to love?

How was he exposed to love at a young age… that is the best indicator as to how he will love his family and you or his lover over time.

Side note:

Different situations require different questions, so if you’re looking for questions for a specific situation, just pick an  article below:

  • If you need questions for a first date refer to this article here,
  • Questions to ask your girlfriend here,
  • Funny first date questions here,
  • Deep questions to ask a girl here,
  • Sexual questions to ask your boyfriend here.

Remember, from childhood, to trauma, to home life, to love, the amount of deep questions and topics you can go into are limitless – it’s about picking the right question for the right time!

5. Did your parents love you unconditionally?

Does he know how to truly love without getting anything back? Does he love just because or does he need a reason or validation in return.

6. Do you project your insecurities onto others?

Is he aware of what he is insecure are or does he blame you for his shortcomings?

7. How do you work through your daily struggles?

Does he meditate about them, go to a counselor or play the victim and complain?

8. How do you heal your own traumas?

Is he accepting of the things he has gone through or has he re-written his story so that he doesn’t have to face reality?

9. Do you go to therapy?

Does he take his mental health seriously?

10. Do you pray or meditate?

Does he believe in a power higher than himself? Does he realize and accept that he does not have to go through life alone?

11. Are you spiritual or religious?

Is he his own idol? Believing in something more is extremely important if you have are at all spiritual.

12. What is one thing you would change about yourself if you could?

Is there anything? Or would one thing change another and cause a domino effect?

13. What is your absolute favorite thing about yourself?

Notice if he mentions something physical, mental, emotional or spiritual about himself. Maybe he will mention the way he makes others feel. This answer will give you a great deal of how deep he truly is.

14. Do you consider yourself an introvert or an extrovert?

Does he like to listen or talk more? Does he like to go out or stay in. Is he the life of the party or asleep at home in bed?

15. Do you get drained around others or do others fill up your well?

Is he energized by other people or from spending time alone in nature?

asking deep questions can make a guy you like open up to you

16. Which parent are you closest to and why?

Mamma’s boy. A boy close to his family is the way to go. How he treats his mother is how he will treat his wife.

17. What was the hardest thing you had to go through in your life?

Does he have a lot of dark stories that molded him or has life been breezy?

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18. Has someone close to you passed away? How did you handle the grief?

Maybe he lost a family member or a close friend. Did he care, does he miss them every single day or did he move on effortlessly? If he feels the pain of missing someone how does he work through it without missing out on his own life?

19. What phase of your life has caused the most growth?

It will be a time of pain, where he thought he wouldn’t get through it but came out on the other side. Often times when you feel like you’re breaking you’re growing and evolving.

20. Do you feel like you’re stuck at a moment in time?

Do things seem stagnant for him? Is he at a standstill with lockdown and work and relationships?

21. How do you express love towards others?

Does he show his love through gift giving, physical touch, quality time, etc.

Maybe he wants to kiss you?

22. How do you need to be loved?

This is a great question for over text as you’ll learn whether he needs a lot to feel loved or is a little text here and there enough.

23. Is your job now your dream job you’ve always wanted?

Does he do something he loves? He will live a sad life if he is doing something he hates.

24. If you could do any job you desired, money not an object, what would it be?

Would he change his career path or stay doing what he is already doing because he loves it?

25. What makes you feel like you’re living with purpose?

What lights him up? Traveling, debates, family, writing, singing…

26. Do you prioritize your health?

Does he take care of his body, watch what he puts into it and workout?

27. What is your favorite book and your favorite movie? Why?

Does he go after the romantic stuff, the dramas, comedies, action movies. What draws him in and captures his attention?

28. What character in a show/movie/book have you related to most and why?

Will he name an outcast, a nerd, a jock, the boy who had it all or the boy who had nothing. Is he the underdog or the boy who always wins?

29. What are the top three qualities you are looking for in a partner?

Does he really think about this one, what is his level of consciousness?

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30. Are you attracted to the physical, mental or spiritual the most?

Does he go after someone because of what they look like, how they think, the way they express themselves or just the vibe in general?

31. Do you believe in second chances?

Does he give people multiple chances for making a mistake? Is he forgiving to a fault?

32. Do you want to get married?

Does he believe happiness is only real when shared?

33. If you have kids how do you want them to describe you?

Is he carrying himself the way he wants to be seen or is there a lot of growing left to be done?

34. Would you describe yourself as having mood swings or a temper?

Is he moody or temperamental?

35. Does family come first?

With this question, you’ll learn how your man thinks about relationships and love in general: is he a family man or the loner type?

36. Would you stay with your significant other if you’re family did not approve?

Does his families opinion overpower his own beliefs? Does he think love can be blind and listen to his family above all?

37. What is your view on politics?

Is he political or indifferent. Is he a debater?

38. Who is the person in your life that you tell anything and everything to without judgement?

Is it a sister, a brother, a childhood friend?

39. Do you think you can be just friends with someone you once loved?

Does he believe in keeping someone in his life even if they can’t be who they once were? Is it possible?

40. When you are upset do you like someone to be there with you or do you like to be left alone?

Is he a hermit or does he move on through movement and expression?

ask him a personal question about whether he likes spending time alone

41. What is your favorite weekend activity?

Does he like cuddling and watching Netflix,

42. Do you think you can be best friends with someone of the opposite sex and keep the relationship platonic?

Can boys and girls be just friends without one of them catching feelings at some point?

43. Do you judge people based on what they look like?

Is he shallow….

44. Are you non-confrontational?

Or confrontational? Passive aggressive or aggressive?

45. Are you a heart breaker or the heart broken?

Is he the one who usually ends things or is he the one who is broken up with?

46. Would you move across the country for someone you love?

Is he a hopeless romantic?

47. What are you most grateful for in life?

Are they people, places he’s been, or the things he possesses?

48. Do you keep a journal, write music, stories, or poems?

Is he the sentimental type?

49. What is an impression people get about you that is wrong?

Do people always assume something about him based on the way he looks or presents himself that is inaccurate? Maybe he has resting bitch face but is the sweetest man to walk the earth.

50. What is a word everyone could agree about to describe you with?

Is there something he can never hide about himself? Maybe it’s his hilarious sense of humor or his complete kindness that everyone uses to describe him.

51. Why did your last relationship end?

Was it just growing apart, or was it something dramatic like cheating?

52. Do you believe all you need for a successful relationship is love?

Or do you need similar long term goals, morals, and religious / political views?

53. How do you feel about online dating like Tinder & Bumble?

Does he get an ego boost from going on sites that just show photos of people?

54. What is an activity that gives you the most adrenaline?

Skydiving, bungee jumping, sex… just to name a few.

55. What is the wildest thing you have ever done?

Is adventure his middle name?

56. Do you believe in living in the present?

Or does he relive the past and think about the future constantly?

57. If you had three wishes what would you wish for right now?

Does he wish for money, love, truth, world peace?

58. Do you have any regrets?

Does he regret choices he has made or is everything a lesson?

59. Where does your mind wander when you’re not doing anything?

Does he replay corrupted scenarios or does he dream and make things happen?

60. Do you have repetitive dreams?

Does he have the same dreams that try and teach him a lesson he can’t grasp? You know what they say, you keep repeating patterns until you learn or until you change.

61. Can you control your own dreams?

Does he lucid dream?

62. How long was your longest relationship?

Has he been able to stay in a long-term relationship or does he crave change?

63. Are birthdays important to you?

And holidays? Does he like celebrating?

64. Do you believe in your birth chart?

Does he read his horoscope and does he find the answers he seeks from his nature?

65. Do you blame your zodiac sign for acting a certain way?

Does he say things like, “I cheated because I’m a Gemini.”

66. How large would you say your ego is?

Does he feed his ego regularly?

67. Are you an avid reader?

Is knowledge important. Is he like a sponge always wanting to absorb new information.

68. Are you more of a talker or a listener?

Does he enjoy listening to others stories or being the story teller?

69. Why do you think you’re apart of this generation?

What does he believe he was put on this planet to change?

70. What are you here to share with the world?

What is his talent that he needs to expose?

71. Do you believe in fate?

What is his destiny?

72. Or do you believe that everything you do is your choice and your choice alone?

Or is free will the way?

73. Do you believe in manifestation?

Does he believe he can think and believe things into existence?

74. Do you believe in karma?

Does he think people get back what they put in?

75. Do you think people are out to sabotage you?

Are people out to hurt him?

76. If you had to listen to one song for an entire day what song would you listen to?

Notice if he names a sad song, a happy song… what kind of mood resonates with him most?

77. Do you enjoy festivals and concerts or would you rather listen to music with your air-pods?

Does he want to be out screaming in the crowds or in a quiet space with his air-pods?

78. Would you switch places with someone for a month if you could? Or do you like your life and yours alone?

Does he ever wish he was someone else?

79. What is your biggest fear in life?

Is he afraid of anything? If he says he isn’t dig deeper, everyone is.

80. Are there any moments in your life when you felt pure ecstasy? Tell me about one.

What is his favorite happy moment? Maybe one with you!

81. If you could take me anywhere in the world where would you take me and why?

Where does he see himself with you? Maybe the oceanside or on a mountaintop?

82. If you could rob a bank without getting caught would you?

How moral is he?

83. What song makes you cry every time you listen to it?

Is there a song he hears that makes him get in his feels every single time?

84. Do you go to church?

Does he know how to PRAY?

85. What is something that always baffles your mind?

Like the stupidity or ignorance of people?

86. Do you believe in past lives?

Has he been here before?

87. If you do, what do you think you were?

Does he think he was a human, or maybe an animal?

88. Have you ever experienced a supernatural event?

In the sky, in his home…

89. Do you believe in demons and angels?

Does he think angels send him messages in numbers, or miracles and demons send temptation?

90. Have you ever been inside a haunted house?

Like a real one, where creeks happen and cats meow at the walls?

91. What is the strangest dream you have ever had?

What kind of strange will he describe…

92. What is your darkest thought that you haven’t told anyone?

Does he have them often?

93. What scares you the most about the overall health of this country?

The economy, politics, healthcare, education?

94. What is one thing you do that always calms you down?

Workout? Yoga?

95. What makes you anxious or uneasy?

Is he an anxious person?

96. Do you believe honesty is the best policy?

Or is a little white lie ok sometimes?

97. Do you believing crying heals?

Tell him it literally releases chemicals to make you happier!

98. If your life was a movie what would the title be?

Take some time and let him contemplate this one for something creative.

99. What is your love language and how do you express your own love?

Does he express his love the same way he needs to be loved?

100. Is home a place or the people you are with?

What makes a moment? The people he knows or the places he goes?

101. Do you ever feel insane because nobody understands you?

Everyone feels totally alone sometimes, but the truth is we never are.

102. What is your most cherished childhood memory?

Does he remember his childhood?

103. Do you often have deja vu?

Are there a lot of a-ha moments in his life or does he feel like he recognizes people or situations from the past?

104. Do you believe people exist on other planets?

Or are we the only ones? Does the thought excite him or scare him?

105. What do you think existed before the universe was created?

Was there anything here before this?

106. Do you believe in parallel universes or other dimensions?

Is there another him in another universe?

107. Do you think art is anything people create?

Or does it take actual talent? Is everyone an artist?

108. If you could change one thing about your body would you?

Or is he completely accepting of how he looks?

109. If you could find out the exact day you will die and how you die would you want to know?

Does he want his days numbered?

110. If you found the fountain of youth and could stay young eternally would you drink from it?

Or is aging a beautiful part of life?

111. Would you rather love or be loved?

Give or be given?

112. Do you believe that sometimes war is necessary?

Peace sometimes can only be found through war. Sometimes love can only be found after hate.

113. What is the difference between joy and happiness?

Does he know joy is internal and happiness is eternal?

114. Are you different around your friends and family?

Is he a different version of himself around different people?

115. If you could choose your death how would you choose to die?

Would it be quick in his sleep, or something crazy like sky diving?

116. Do you believe in monogamy?

Is there that one person he wants for forever?

117. If you could spend one day with any person from the past or present who would it be and why?

Does he choose a political, religious or just your average person?

118. What is your spirit animal and why?

Is he drawn to a certain animal, maybe one he was in a past life…

119. Do you have a desire to go into outer space?

Or is he content traveling what is to be seen on this planet?

120. Would you consider yourself more emotional or rational? A thinker or a feeler?

Does he react out of emotion or think things through?

121. Are you a jealous person?

Is he worried about what others are doing and have FOMO?

122. Do you wish anyone ill?

Is there anyone out there that hurt him so bad he wants to see them fail?

123. Is it better to be right or better to be kind?

Does he want to be nice or correct? Is kindness the newest currency?

124. What is the most romantic thing you have done for someone?

Has he lost his romance because it was not appreciated?

125. What it the most romantic thing that has been done for you?

Has anyone shown him any romance?

126. What quote do you live by?

What is his inspirational daily motivation?

127. How do you hope to be remembered?

As the guy who’s most liked and made everyone’s day, or as the most buff at the gym?

128. What do you want your last words to be?

Something funny, cute, fun, or serious?

guys like it when girls ask deep, personal questions

129. What do you want your tombstone to have on it?

Short and sweet?

130. If you could fix poverty or the education system which one would you choose?

What is more important and which on would have the permanent fix?

131. Do you think living and being alive are the same?

Does he realize the difference?

132. Do you think morality exists in nature or was man-made?

Does everyone have a moral compass?

133. Do you believe technology is more positive or negative?

How does he feel about technology as a whole? Good or bad?

134. Do you think humans are naturally selfish?

Or selfless? Or a mix?

135. Do you think the healthcare system is out to help people or to make money?

Money money money, the way of America.

136. Do you think toxic relationships are alluring?

The brain actually changes when in a toxic relationship… that is why people stay.

137. Have you ever had a near death experience?

Almost run over by a car? Or crashed?

138. What is something you are judgmental about?

Does he judge people on their appearance or on their intelligence?

139. Do you consider yourself open minded?

Hint… a lot of people who think they are open minded are actually close minded.

140. Is there a specific moment in your life that made you a different person?

This one will probably click right away.

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141. How do you express yourself?

Does he use his words or his actions?

142. If your whole life was a picture what would the picture be of?

A beach, a night sky, a place?

143. If you could share one piece of advice with the world what would it be?

Would it be happy, sad, or just life knowledge?

144. What is your most prized possession?

A camera, computer, old stuffed animal?

145. Do you forgive easily or hold grudges?

Or does it depend on the situation?

146. Do you believe that sex opens up spiritual realms and is a sacred act?

Or does he like one-night stands and move from one to the next?

147. Do people expect a lot from you?

Is he just always there, like a rock, stable and steady?

148. What is the American Dream to you?

Is he living it?

149. Have you ever battled depression or other mental illness?

How does he continually push himself out of a bad state or mindset?

150. Would you rather marry someone you don’t truly love than be alone?

Is it better to be alone or to be unsatisfied?


These 150 deep questions will give you just about every answer you need to understand who someone is and why they are the way they are.

People become who they are based on their experiences and their perceptions of reality.

Ask the hard things and live more authentically.

Colt Smith

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About the author 

Coach Colt here, the founder of Dating Armory, your go-to source for no-nonsense, practical relationship advice. I'm a bisexual male in a same-sex open relationship and a researcher in sex, love, and relationships with 7+ years of experience. I specialize in helping both men and women navigate the crazy world of dating.

Don't miss my other guides packed with practical dating advice (no bullshit repeated Platitudes) and tons of real life examples:

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