450+ Deep Questions to Ask a Girl, a Guy, Your Friends

If you find someone you feel a deep, immediate bonding with, ask them the following deep questions to find out more about them and get to know them on an intimate level

Below we’ve got some deep questions to ask that is far from light and fluffy icebreakers. These deep questions are the perfect questions to get to know someone. These questions are great for dates, friends you know well, or person can be your boyfriend or girlfriends who like serious conversations.

Deep Questions To Ask

1. Are humans fueled by greed or by love?
2. Are you a cat or a dog person, and why?
3. Are you a dreamer or a go-getter?
4. Are you a leftie or right-handed, and would you be willing to switch?
5. Are you a morning or a night person?
6. Are you a mountain or a beach person?
7. Are you a religious or spiritual person? Tell me why and tell me how.
8. Are you afraid of dying?
9. Are you assertive or a pushover?
10. Are you close to your parents, and why?
11. Are you confrontational?
12. Are you health conscious?
13. Are you left- or right-handed, and would you want to switch?
14. Are you more afraid of failure or success, and why?
15. Are you more into looks or brains?
16. Are you religious or spiritual?
17. Are you willing to lay down your life for someone, and who is it?
18. Are you willing to relocate for love?
19. Are you willing to share your password with your romantic partner, and why?
20. As a force, are we humans creative or destructive?
21. At this point in your life, what is it that you wish your family knew about you?
22. At what age did you have your first pet, and what was it?
23. At what age do you think people should get married?
24. ​At what age do you think people should think of settling down?
25. Can humans avoid being in love?
26. Can the world really achieve lasting peace?
27. Can you pinpoint the moment in your life where you were the happiest?
28. Can you remember a time in your life you felt the most alive? Tell me everything about that memory.
29. Can you remember the last time you cried, and what was the reason?
30. Deja-vu: is there anything to it or merely coincidence?
31. Describe your best first kiss.
32. Did you ever write a journal?
33. Do you agree that people never change, they just show their true colors?
34. Do you approve of stealing from the rich to give to the poor?
35. Do you believe in burning bridges when it comes to exes?
36. Do you believe in extraterrestrial life? Elaborate on why or why not.
37. Do you believe in fate, or do you think that things happen because of our decisions?
38. Do you believe in giving people second chances, and why?
39. Do you believe in life after death, and why?
40. Do you believe in magic or in science?
41. Do you believe in materialism or spirituality?
42. Do you believe in other dimensions and parallel universes?
43. Do you believe in second chances?
44. Do you believe more in fate or that we are the creators of our own destinies because we are governed by free will?
45. Do you believe that each of us has a soul mate?
46. Do you believe that each one of us has a special mission in life?
47. Do you believe that people of the opposite sex can be the best of friends?
48. Do you believe that the day will arrive when humans will be replaced by machines in almost all aspects of life?
49. Do you believe that the day will come when computers will be more intelligent than humans?
50. Do you believe that the present is really better than in the past?
51. Do you believe we make our own happy endings, or is fate responsible for them?
52. Do you believe yourself to be truly free? If so, why? If not, what is holding you back?
53. Do you consider yourself an introvert or an extrovert?
54. Do you consider yourself spiritual or religious?
55. Do you ever keep a journal?
56. Do you feel happy when you use social media?
57. Do you feel that you’re making a difference with the way you live your life?
58. Do you find it difficult to admit that you are wrong, and why?
59. Do you get excited or scared when meeting new people?
60. Do you give advice to others, and why?
61. Do you have a favorite book? A line in a piece of literature? A poem? Why do you relate to it?
62. Do you have a favorite place in the world, and where is it?
63. Do you have a life’s purpose, and what is it?
64. Do you have any recurring dreams or nightmares?
65. Do you judge a book by its cover?
66. Do you keep a diary, and if yes, how often do you write in it?
67. Do you like who you are now?
68. Do you like your given name, and why or why not?
69. Do you listen to other people’s advice or do you prefer figuring things out yourself?
70. Do you prefer looks or brains?
71. Do you prefer someone cheering you up, or being left alone when you’re in a foul mood?
72. Do you regret anything in life?
73. Do you see the glass as half-full or half-empty?
74. Do you think God is real, and why?
75. Do you think people fall in love because the right person has arrived, or because the time is right (regardless of whom the person is that they fall in love with)?
76. Do you think that cheating partners should be given a second chance?
77. Do you think that humans are doing more harm than good to the planet?
78. Do you think that men are more rational and women are more emotional?
79. Do you think that people can find true love online?
80. Do you think that some lives are more precious than others?
81. Do you think you will be a great parent, and why?
82. Do you usually stay friends with your exes?
83. Do you wish to be famous?
84. Does art have any significance in society?
85. Does your job make you happy?
86. Dogs or Cats?
87. Has another’s pain ever given you joy? Be totally honest.
88. Have you always had the same political beliefs? Is there something that impacted them?
89. Have you broken someone’s heart recently?
90. Have you ever asked a guy out on a date?
91. Have you ever been in love? Tell me about the times you have been.
92. Have you ever been unable to sleep? What do you do with your time then?
93. Have you ever broken someone’s heart?
94. Have you ever cried tears of joy?
95. Have you ever had a brush with death?
96. Have you ever had dreams about a past life?
97. Have you ever lost someone who’s very close to you?
98. Have you ever questioned your sanity and why?
99. Have you ever seen something you can’t explain?
100. ​Have you ever stayed up all night to wait for sunrise?

Deep Questions To Ask A Girl

1. Have you experienced any miracle in your life?
2. Have you experienced losing someone you care a lot about?
3. Have you had your heart broken before?
4. Have you made someone cry?
5. Have you seen an extreme example of poverty, and if so, how would you describe it?
6. How do you cope when things are not going your way?
7. How do you cope with stressful situations?
8. How do you define “a life well lived?”
9. How do you define art?
10. How do you define beauty?
11. How do you define evil, and do you believe that a person can be evil?
12. How do you feel about a cheating partner?
13. How do you feel about infidelity?
14. How do you feel about sharing your password with your partner?
15. How do you feel about the #MeToo movement?
16. How do you rank these three according to importance: career, family, love?
17. How do you think people see you?
18. How do you wish people will remember you after you’re gone?
19. How do you wish to be remembered?
20. How happy are you right now?
21. How important is trust in a relationship?
22. How judgmental are you?
23. How meaningful is your life?
24. How real is God?
25. How will our civilization go extinct?
26. How would people close to you describe you in three words?
27. How would you describe honor?
28. How would you describe the perfect day?
29. How would you describe your best friend?
30. How would you describe your first crush?
31. How would you describe your perfect vacation?
32. How would you live your remaining days if you found out you had only a week to live?
33. How would you rank the following in importance: family, career, love life?
34. How would you spend your remaining time if you found out you only had 10 days left to live?
35. How would you summarize your life purpose?
36. How would your best friend describe you in five words?
37. If “hello” were to be replaced by another word as a greeting, what word would that be?
38. If a genie granted you 3 wishes right now, what would you wish for?
39. If all your wishes were granted today, how would you describe your life five years from now?
40. If heaven is real and you died tomorrow, would you get in?
41. If I asked you at age 5 what you wanted to be when you grew up, what would you say?
42. If past lives are real, what was yours?
43. If there were a universal way of greeting, what should it be?
44. ​If they made a movie about your life, who would you choose as the director and why?
45. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?
46. If you could be anywhere other than where you are right now, where would you be and what would you be looking at?
47. If you could be given the date of your death would you want to know it?
48. If you could be President of your country for an hour, what is the one thing that you would change?
49. If you could change one thing about the world what would it be?
50. If you could change one thing about yourself what would it be?
51. If you could do one thing without suffering the consequences, what would
    you do?
52. If you could get away with anything that you do?
53. If you could have any animal in the world as a pet, what would it be and why?
54. If you could have anybody else’s life, whose would you take?
55. If you could have the option of eradicating pain from your life would you choose to do so? Why or why not?
56. If you could live anywhere in the world where would it be?
57. If you could swap lives with someone for a day, who would you choose and why?
58. If you could take us anywhere in the world right now, where would you take us?
59. If you could tell your former self one thing right now what would it be?
60. If you die tonight, would you pass away fulfilled or unsatisfied with life?
61. If you died tomorrow, what would you wish you had done?
62. If you died tonight, what would you regret not doing?
63. If you got a free cheque for $5,000 right this second, how would you use it?
64. If you had a billion dollars, how would you use the money to benefit the less privileged?
65. If you had the ability to erase something that you did in the past, what
    would it be?
66. If you had to pick one, what is the most important value you would teach your children? Honesty, Kindness or Courage?
67. If you have to lay your life on the line for someone, who would that person be?
68. If you were born in another era, when would that period in history be and why?
69. If you were forced to pick one religion on this planet, which one would it be and why?
70. If you were forced to vote for one the biggest dictators of history, (Hitler, Mussolini, Mugabe, Mao, Saddam or Stalin), which one would you pick and why?
71. If you were given a chance to explore the oceans, go to outer space or visit 50 different countries, which one you choose and why?
72. If you were given a chance to swap places with somebody for a day, who would you choose?
73. If you were given a choice to choose your manner of death, how would you die?
74. If you were given a choice to turn into a zombie or to die, which would you pick?
75. If you were given a million dollars today, how would you spend it within three days?
76. If you were given free rein to design the ideal metropolis, what would your city be like?
77. If you were given the chance to live anywhere in the world, where would you stay?
78. If you were given three things to make you happy, what would these be?
79. If you were in a band, what instrument would you play?
80. If you were offered an all-expense-paid plastic surgery, would you accept it, and what would you change about your physical appearance?
81. ​If you were stranded on a deserted island, what three items that are not electronic or automatic would you take with you?
82. If you were to die tonight, would you die as a fulfilled or an unsatisfied person?
83. If you were to give up one of your senses, what would it be?
84. If your life was a movie or a book what would be the title to it?
85. If your life was a movie, what would the title be and why?
86. Imagine that you are tasked to re-design society… what changes would you make?
87. In what manner do you think you will die?
88. Is a life exclusive to pleasure (no suffering) worthwhile?
89. Is happiness a state of mind or we need to act in order to achieve it?
90. Is home for you a place or a feeling? Describe that place or describe that feeling.
91. Is there a film or cartoon character who is very much like you? In what way?
92. Is there an activity that calms you? A place or a thing that makes you feel at ease?
93. Is there any decision that you feel guilty about making in your personal life?
94. Is there any part of your personality that you feel you need to improve? If so, which part and why?
95. Is there anything that you would like to change about yourself?
96. Is there somebody you would consider “the one who got away”?
97. Is there something out there, a thought, an idea, a current event, or a fear that you find deeply unsettling?
98. Is there such a thing as absolute freedom?
99. Is there such a thing as lasting peace?
100. Is what you’re doing now what you always wanted to do growing up?

Deep Questions To Ask A Guy

1. Is your job now a reflection of what you said you wanted to be when you were a kid?
2. Is your life going in the direction you want?
3. Name one really surprising thing that set your heart pumping and gave you an adrenaline rush.
4. Name the one bad quality you wouldn’t mind in a partner.
5. Name the one worst quality you cannot tolerate in a partner.
6. On a scale of 1 to 10, how fulfilled are you about life?
7. Out of the negative emotions of greed, anger, jealousy, and hate, which one would you say affects you the most?
8. Out of the positive emotions of compassion, positivity, enthusiasm, and initiative, which one is your biggest strength?
9. Pick two out of physical chemistry, lifestyle compatibility, emotional compatibility, and intellectual compatibility.
10. Presented with the opportunity to be immortal would you take it?
11. Show me a music track or a scene from a film that made you tear up.
12. Tell me a really, really stupid joke that made you laugh.
13. Tell me about the facts or harsh truths you choose to ignore but know you shouldn’t.
14. Tell me about the time you were so embarrassed in love, you wished you could disappear right there and then.
15. Tell me about the time’s someone broke your heart.
16. Tell me about your biggest love regret that made you wish you could turn back time?
17. Tell me your biggest strength outside of your workplace.
18. Tell me your biggest supernatural or paranormal fear?
19. Think about the people you love the most in your life, what do you do for them?
20. Was there a book that influenced you the most?
21. ​What ability do you possess that you’d think others would find amazing?
22. What accomplishment are you most proud of?
23. What are some of your favorite songs?
24. What are some of your own personal goals in the next 5 years?
25. What are the top five things you are grateful for?
26. What are the two greatest lessons you’ve learned from a past relationship?
27. What are three things that are on your bucket list?
28. What are three things you value most about a person?
29. What are you most proud of in your life?
30. What are you most thankful for?
31. What are you passionate about in life?
32. What are your thoughts on online dating or tinder?
33. What are your top five favorite movies?
34. What book and movie spoke to you, and in what way?
35. What book influenced you the most?
36. What did you do when you hurt someone the most?
37. What did you want to be when you were younger?
38. What did your past relationship teach you?
39. What do people constantly misunderstand about you?
40. What do you do or where do you go when you need to be alone?
41. What do you feel is the right age for people to get married?
42. What do you feel is your greatest accomplishment to date?
43. What do you look for in a relationship?
44. What do you regret doing in life?
45. What do you think about when you’re by yourself?
46. What do you think are the two things that prevent people from realizing their dreams?
47. What do you think happens after death, if anything?
48. What do you think is humankind’s greatest invention?
49. What do you think of best friends of the opposite sex?
50. What do you think was there before the universe came into creation?
51. What do you think will bring about humanity’s extinction?
52. What excites you the most?
53. What fashion piece would you invent for women?
54. What fictional character do you most relate to?
55. What food could you not live without?
56. What gives your life meaning?
57. What has been the biggest change you ever made that made you the proudest of yourself?
58. What important lesson did a close relative teach you?
59. What important lesson have you learned from a family member?
60. What is a relationship deal breaker for you?
61. What is more important: being true to yourself regardless of who gets hurt or considering the consequences of your actions on other people’s lives?
62. What is one dream you have yet to accomplish?
63. What is something that you are proud of about yourself?
64. What is that one thing other people do that you find amusing?
65. What is the craziest thing you’ve ever done and would you do it again?
66. What is the darkest thought you’ve ever had? What about the darkest thing you’ve never told anybody?
67. What is the first lie you ever told? Which is the biggest?
68. What is the first secret you ever kept from anybody? Which is the biggest?
69. What is the greatest invention of this age?
70. What is the greatest struggle you’ve overcome?
71. What is the most adventurous thing you have ever done in your life?
72. What is the most astonishing act that a person can do for you?
73. What is the most awkward situation you’ve experienced recently?
74. What is the most romantic and loving thing you have ever done for somebody?
75. What is the perfect life for you?
76. What is the single most important thing people should do for the planet?
77. What is the strangest dream you’ve ever had?
78. What is the value of art in society?
79. What is the weirdest thing about you?
80. What is the weirdest thing that your family does together?
81. What is your best childhood memory?
82. What is your biggest accomplishment?
83. What is your biggest irrational fear?
84. What is your biggest regret?
85. What is your biggest turn-off in a relationship?
86. What is your definition of a “perfect life”?
87. What is your definition of fame?
88. What is your description of a perfect weekend?
89. What is your favorite motivational quote?
90. What is your favorite part of a house, and why?
91. What is your favorite song and why?
92. What is your favorite workout routine?
93. What is your funniest memory of high school?
94. What is your greatest fear?
95. What is your idea of a perfect date?
96. What is your idea of a perfect vacation?
97. What is your ideal vacation?
98. What is your life’s soundtrack?
99. What is your major turnoff in a romantic relationship?
100. What is your most cherished childhood memory?

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More Deep Questions

1. What is your personal philosophy in life?
2. What is your pet peeve in the workplace?
3. What is your secret hobby that others would consider weird?
4. What is your take on astrology?
5. What is your take on telepathy?
6. What is your view about monogamy?
7. What is your worst memory of elementary school?
8. What kind of parent do you think you will be?
9. What legacy do you want people to remember about you after you’re gone?
10. What life-changing event have you experienced?
11. What long-held belief did you have that was recently disproved by science?
12. What made you choose the college you went to?
13. What makes you feel accomplished?
14. What makes you feel like you need to be alone?
15. What makes you feel uneasy? Overwhelmed? Anxious?
16. What makes you nostalgic?
17. What movie influenced you the most?
18. What musical instrument do you know how to play?
19. What mythical animal do you resonate with, and why?
20. What part of your body do you find attractive?
21. What period of history would you change if given the chance?
22. What qualities are you looking for in a partner?
23. What qualities do you admire about your parents?
24. What quality in a person do you fall in love with?
25. What quote resonates with you more than any other?
26. What realities or truths are you in denial about?
27. What regrets would you have if you were to die today?
28. What scene in a movie has evoked the most feelings out of you?
29. What secret trait do you wish that people know about you?
30. What skill do you envy in other people?
31. What skill do you wish you had?
32. What song do you often sing in the shower?
33. What song makes you unconditionally happy?
34. What song makes you unconditionally sad?
35. What sport did you fall in love with?
36. What subject were you good at in high school?
37. What superpowers did you wish you had when you were a kid?
38. What task would you really fail at doing?
39. What things or situations make you feel unsure about yourself?
40. What three adjectives would describe you?
41. What three non-electric or non-automatic items would you take on a deserted island?
42. What top five lessons have you learned the hard way?
43. What trait do you envy in others?
44. What two items would you need to survive an apocalyptic zombie invasion
45. What was it like growing up in your hometown?
46. What was the best phase of your life?
47. What was the last book you read? And When?
48. What was the most embarrassing thing that you did for someone you love?
49. What was the most embarrassing thing that you’ve done for a friend?
50. What was the most important lesson you’ve learned from your past relationship?
51. What was the most memorable experience you had in elementary school?
52. What was the title of the first movie you watched in a movie theater?
53. What was the worst phase in your life?
54. What was your best birthday?
55. What was your biggest “facepalm” moment?
56. What was your experience about being “mansplained,” and what did you do about it?
57. What was your father or mother like at home? How does he or she act different outside of the family?
58. What was your longest relationship?
59. What was your most embarrassing experience at work?
60. What was your most memorable adventure when you were 10 years old?
61. What was your most memorable birthday?
62. What will people say about you at your funeral?
63. What word or term do you wish to know the meaning of?
64. What would be the title of the movie showing your life from birth up to present?
65. What would be your supervillain name and your powers?
66. What would be your thought process if you were presented with irrefutable evidence that a god didn’t exist? What would be your thought process if you were presented with irrefutable evidence that a god did exist?
67. What would the world be like if you hadn’t been born?
68. What would you consider to be your deepest fear? (This question can be really telling of the depth or lack thereof of a person.)
69. What would you consider your greatest accomplishment so far?
70. What would you do for the people you love?
71. What would you do if your parents did not approve of your partner?
72. What would you do if your parents didn’t like your partner?
73. What would you want to be famous for?
74. What would your best friend say is your best quality?
75. What would your three wishes be if someone could make them come true?
76. What, for you, is the ultimate comfort food?
77. What’s a deal-breaker for you in a relationship?
78. What’s the ideal weekend for you?
79. What’s been your biggest mistake so far in life and what did you learn from it?
80. What’s closest you’ve ever come to being arrested?
81. What’s on your bucket list this year?
82. What’s one item you’ve recently crossed off your bucket list?
83. What’s one thing that bothers you most about the world today?
84. What’s one thing you wish you knew how to do?
85. What’s something you can’t go a day without doing?
86. What’s the craziest thing you’ve ever done for love?
87. What’s the greatest risk you’ve ever taken?
88. What’s the highest point you’ve experienced in your life this year?
89. What’s the lowest point in your life this year?
90. What’s the most exciting thing that’s happened this past year?
91. What’s the most spontaneous thing you’ve done lately?
92. What’s the one thing that people always misunderstand about you?
93. What’s the one thing you would like to change about yourself?
94. What’s the one trait or personality you’d like to change about yourself?
95. What’s the perfect day for you?
96. What’s your anti-motto?
97. What’s your biggest pet peeve?
98. What’s your biggest regret in life?
99. What’s your day-to-day mantra?
100. What’s your favorite beer?
101. What’s your favorite book/movie of all time and why did it speak to you so much?
102. What’s your favorite hobby to do alone?
103. What’s your philosophy in life?
104. When do you think a person is ready for marriage?
105. When have you caused the most harm to yourself?
106. When have you felt like you were living life to the fullest? When have you felt like you weren’t?
107. When have you felt the lowest in your life?
108. When have you felt your biggest adrenaline rush?
109. When was the last time you broke someone’s heart?
110. When was the last time you laughed so hard?
111. When was the last time you said “I love you” to someone?
112. When was the last time you slept outdoors?
113. ​When was the last time you slept under the stars?
114. When was the last time you spoke with a classmate from high school?
115. When was the last time you were moved to tears by a movie?
116. When you die, would you prefer to be alone or surrounded by people you know?
117. When you were a kid, what did you say you wanted to be when you grew up?
118. When you were growing up, which superhero was your favorite and why?
119. When you’re alone, what do you usually think of?
120. Where do you find meaning in your life?
121. Where do you usually get your news?
122. Where does happiness come from? Define what happiness means to you.
123. Where have you felt the most failure? The most success?
124. Where is your favorite place in the entire world to go?
125. Where’s one place you’d like to go that you haven’t been?
126. Which emotion best represents you, and why?
127. Which is the better option: being a heartbreaker or being heartbroken?
128. Which member of your family do you feel closest to, and why?
129. Which of your habits would other people consider weird?
130. Which one is a better situation: broke or lonely?
131. Which one wins: reality or imagination?
132. Which parent are you closer to and why?
133. Which would you choose to be: law-abiding citizen or rule breaker, and why?
134. Which would you prefer in a romantic partner: a dreamer or an achiever?
135. Which would you prefer: having a baby without a partner or a partner without a baby?
136. Who are five people you are closest with?
137. Who are you closer with your mom or your dad?
138. Who do you consider your best friend in your workplace?
139. Who do you feel is your closest confidant among your family members?
140. Who do you look up to in life?
141. Who is that one person you can talk to about just anything?
142. Who is the fictional character who closely resembles you in terms of attitude?
143. Who is the person with whom you can talk about anything?
144. Who is your favorite historical figure?
145. Who is your greatest hero?
146. Who is your real-life hero?
147. Who or what inspires you?
148. Who was your favorite cartoon character when you were a kid?
149. Who was your favorite teacher and why?
150. Who’s hiding behind the mask you present to the world?
151. Why are we here?
152. Why did you cry the last time you did so?
153. Why did your last relationship end?
154. Why do you think people believe in conspiracy theories?
155. Why do you think you’re still single?
156. Will you encourage the younger generation to use social media?
157. Would you be willing to go the extra mile for something or someone?
158. Would you do a crazy thing for a friend?
159. Would you ever take back someone who cheated?
160. Would you find more comfort in the theoretical idea that we were the most advanced species in outer space or would you find more comfort in the idea that we weren’t?
161. Would you lay down your life for someone?
162. Would you rather be a world-famous pro-MMA athlete or the president of a country?
163. Would you rather be called vain or insecure?
164. Would you rather be loved or love?
165. Would you relocate for love?
166. Would you relocate to a place where you don’t have any family or friends?
167. Would you wait for the sun to rise or for it to set, and why?

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