371 Deep Questions to Ask a Girl, a Guy, Your Friends, or Even Yourself

One of the best ways to get to know someone is by asking open-ended questions. Even though many questions might sound generic and it may only incite small talk, the responses are usually very revealing. They give you a glimpse into a person’s true nature. Sometimes, answers to personal questions will even reveal what an individual often hides from others or is afraid to tell most people.

Sounds heavy, right?

But really, if you want to get to know a person beyond the basic biographical information of their name, birth date, and hometown, then you need a list of deep questions to ask during conversations.

Deep questions are not only ideal for getting to know others better; you can also use them to become better acquainted with yourself, especially if you are searching for your purpose in life.

This post contains 371 deep questions that will help you:

• Get answers to reveal a person’s true character
• Discover the things they value the most
• Understand their capacity for humor (or lack of humor)
• Gauge their intelligence
• Learn about their level of compassion

To simplify things, we have broken down this post into four basic categories. You will discover deep questions to ask:

• A girl
• A guy
• Yourself
• Your family or friends (or people you’d like to turn into friends)

Remember that although these questions are great for getting the conversation going, you must be attentive to the answers and ask for details when necessary. As much as possible, even with the more serious questions, keep the “interrogation” light and lively. (Which is why we highly recommend you focus on the practice of mindful listening.)

OK, let’s get digging!

(Sidebar: ​Asking deep questions and improving the quality of your conversations is skill that can be developed -- if you treat it like a habit.  So if you'd like to learn how to build simple, daily habits that will help your ​relationship goals, then I suggest checking out this book, which has 127 small changes to improve your health, wealth, and happiness.​)

91 Deep Questions to Ask a Girl

If you’re looking for ways to know a girl better, these get-to-know-you questions can help you dig further and reveal more about her personality.

These questions help keep your conversation going, and at the same time, allow you to discover more about her. With these questions, you’ll learn about her life’s story and how it has shaped her in the present, what her tastes are, and how she views other people, among other things.

You can use these more personal questions to start up new conversations instead of revisiting the same old conversations again and again. New topics will lead to learning how someone really feels about something, and this small talk can ultimately lead to a deep and meaningful conversation that can lead to a healthy relationship.

1. If you were given three things to make you happy, what would these be?
2. How would you rank the following in importance: family, career, love life?
3. Which would you prefer: having a baby without a partner or a partner without a baby?
4. What was your experience about being “mansplained,” and what did you do about it?
5. Who was your favorite cartoon character when you were a kid?
6. Do you think God is real, and why?
7. Do you believe in giving people second chances, and why?
8. How would you describe your first crush?
9. Do you ever keep a journal?
10. 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)?
11. How do you feel about the #MeToo movement?
12. What do you look for in a relationship?
13. What is your idea of a perfect date?
14. What legacy do you want people to remember about you after you’re gone?
15. Have you ever asked a guy out on a date?
16. What was the most important lesson you’ve learned from your past relationship?
17. What book influenced you the most?
18. What life-changing event have you experienced?
19. What’s a deal-breaker for you in a relationship?
20. Are you a morning or a night person?
21. How important is trust in a relationship?
22. How do you feel about infidelity?
23. Do you believe that the day will arrive when humans will be replaced by machines in almost all aspects of life?
24. What do you think is humankind’s greatest invention?
25. Do you think that humans are doing more harm than good to the planet?
26. What is your take on telepathy?
27. What is your favorite workout routine?
28. Would you rather be called vain or insecure?
29. What important lesson did a close relative teach you?
30. What part of your body do you find attractive?
31. Which would you choose to be: law-abiding citizen or rule breaker, and why?
32. What is your ideal vacation?
33. What superpowers did you wish you had when you were a kid?
34. Are you a mountain or a beach person?
35. What mythical animal do you resonate with, and why?
36. Which member of your family do you feel closest to, and why?
37. Who do you consider your best friend in your workplace?
38. What three adjectives would describe you?
39. If you could live anywhere in the world, where would you choose?
40. What are you passionate about in life?
41. What quality in a person do you fall in love with?
42. Have you had your heart broken before?
43. What is your take on astrology?
44. What is your life’s soundtrack?
45. When was the last time you spoke with a classmate from high school?
46. Are you left- or right-handed, and would you want to switch?
47. What subject were you good at in high school?
48. What was the most memorable experience you had in elementary school?
49. Do you find it difficult to admit that you are wrong, and why?
50. Do you get excited or scared when meeting new people?
51. What is your secret hobby that others would consider weird?
52. How do you cope with stressful situations?
53. Is there anything that you would like to change about yourself?
54. What musical instrument do you know how to play?
55. Who or what inspires you?
56. Which would you prefer in a romantic partner: a dreamer or an achiever?
57. What is your favorite part of a house, and why?
58. Who is the fictional character who closely resembles you in terms of attitude?
59. When you were a kid, what did you say you wanted to be when you grew up?
60. What was the title of the first movie you watched in a movie theater?
61. When was the last time you slept outdoors?
62. What is something that you are proud of about yourself?
63. What song do you often sing in the shower?
64. What do you feel is the right age for people to get married?
65. What would be your super villain name and your powers?
66. What three non-electric or non-automatic items would you take on a deserted island?
67. If “hello” were to be replaced by another word as a greeting, what word would that be?
68. What is the weirdest thing that your family does together?
69. What was the most embarrassing thing that you’ve done for a friend?
70. What task would you really fail at doing?
71. What is your definition of a “perfect life”?
72. What would be the title of the movie showing your life from birth up to present?
73. What fashion piece would you invent for women?
74. What is the single most important thing people should do for the planet?
75. How do you define evil, and do you believe that a person can be evil?
76. What do you think are the two things that prevent people from realizing their dreams?
77. Would you lay down your life for someone?
78. What word or term do you wish to know the meaning of?
79. What makes you nostalgic?
80. Do you believe that each of us has a soul mate?
81. How would you live your remaining days if you found out you had only a week to live?
82. Do you listen to other people’s advice, or do you prefer figuring things out yourself?
83. What is your favorite motivational quote?
84. Imagine that you are tasked to re-design society - what changes would you make?
85. What’s the perfect day for you?
86. Would you wait for the sun to rise or for it to set, and why?
87. If you were born in another era, when would that period in history be and why?
88. Have you made someone cry?
89. What is the most astonishing act that a person can do for you?
90. 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?
91. If you die tonight, would you pass away fulfilled or unsatisfied with life?

90 Deep Questions to Ask a Guy

As with the get-to-know-you questions for a girl, this set of queries has the potential to reveal the true personality of the guy you are asking them of.

Ask follow-up questions to the answers given to you. Learn to read between the lines in his answers, as sometimes the things that are being said are colored by the things you want to hear.

1. How would you describe the perfect day?
2. Is there any decision that you feel guilty about making in your personal life?
3. What movie influenced you the most?
4. At what age do you think people should think of settling down?
5. If you were stranded on a deserted island, what three items that are not electronic or automatic would you take with you?
6. If they made a movie about your life, who would you choose as the director and why?
7. What ability do you possess that you’d think others would find amazing?
8. Have you ever stayed up all night to wait for sunrise?
9. When was the last time you slept under the stars?
10. Would you rather be a world-famous pro-MMA athlete or the president of a country?
11. Can you remember the last time you cried, and what was the reason?
12. Who do you feel is your closest confidant among your family members?
13. If you were given a million dollars today, how would you spend it within three days?
14. What two items would you need to survive an apocalyptic zombie invasion
15. When you were growing up, which superhero was your favorite, and why?
16. What is your funniest memory of high school?
17. How would you spend your remaining time if you found out you only had 10 days left to live?
18. What’s one item you’ve recently crossed off your bucket list?
19. Do you have a favorite place in the world, and where is it?
20. Are you a cat or a dog person, and why?
21. Are you more afraid of failure or success, and why?
22. What was your most memorable birthday?
23. At what age did you have your first pet, and what was it?
24. What things or situations make you feel unsure about yourself?
25. What do you feel is your greatest accomplishment to date?
26. What would you do for the people you love?
27. At this point in your life, what is it that you wish your family knew about you?
28. When was the last time you said “I love you” to someone?
29. If you have to lay your life on the line for someone, who would that person be?
30. Do you believe in fate, or do you think that things happen because of our decisions?
31. What period of history would you change if given the chance?
32. Who is your real-life hero?
33. What was it like growing up in your hometown?
34. If you were to give up one of your senses, what would it be?
35. What was your most embarrassing experience at work?
36. Are you a leftie or right-handed, and would you be willing to switch?
37. How would people close to you describe you in three words?
38. What skill do you envy in other people?
39. What is your pet peeve in the workplace?
40. What is your view about monogamy?
41. Have you ever broken someone’s heart?
42. What was your biggest “facepalm” moment?
43. How happy are you right now?
44. What was the most embarrassing thing that you did for someone you love?
45. Have you experienced losing someone you care a lot about?
46. If you were offered an all-expense-paid plastic surgery, would you accept it, and what would you change about your physical appearance?
47. Are you a dreamer or a go-getter?
48. What important lesson have you learned from a family member?
49. Do you agree that people never change, they just show their true colors?
50. How do you wish people will remember you after you’re gone?
51. What qualities are you looking for in a partner?
52. Are humans fueled by greed or by love?
53. What, for you, is the ultimate comfort food?
54. Have you ever had a brush with death?
55. If you were in a band, what instrument would you play?
56. If you were given a chance to swap places with somebody for a day, who would you choose?
57. Do you like your given name, and why or why not?
58. Are you afraid of dying?
59. Do you have a life’s purpose, and what is it?
60. Is there somebody you would consider “the one who got away”?
61. Do you see the glass as half-full or half-empty?
62. What is that one thing other people do that you find amusing?
63. If you were given the chance to live anywhere in the world, where would you stay?
64. How do you cope when things are not going your way?
65. Is there a film or cartoon character who is very much like you? In what way?
66. Which of your habits would other people consider weird?
67. What is your biggest turn-off in a relationship?
68. Do you believe we make our own happy endings, or is fate responsible for them?
69. What long-held belief did you have that was recently disproved by science?
70. What was your most memorable adventure when you were 10 years old?
71. Is there any part of your personality that you feel you need to improve? If so, which part and why?
72. What is the most awkward situation you’ve experienced recently?
73. If there were a universal way of greeting, what should it be?
74. In what manner do you think you will die?
75. As a force, are we humans creative or destructive?
76. Why do you think people believe in conspiracy theories?
77. How would you describe honor?
78. What is the value of art in society?
79. Can the world really achieve lasting peace?
80. Do you think that some lives are more precious than others?
81. What is the perfect life for you?
82. Do you believe that the day will come when computers will be more intelligent than humans?
83. How will our civilization go extinct?
84. Is happiness a state of mind or we need to act in order to achieve it?
85. How do you rank these three according to importance: career, family, love?
86. How real is God?
87. Was there a book that influenced you the most?
88. What do you regret doing in life?
89. What are you most proud of in your life?
90. If you were to die tonight, would you die as a fulfilled or an unsatisfied person?

92 Deep Questions to Ask Your Friends

Asking deep, get-to-know-you questions can often strengthen the bonds of friendship.

Although you may already know them at a certain level, their answers to some of these questions may surprise you and bring you closer together.

1. If you died tonight, what would you regret not doing?
2. What will people say about you at your funeral?
3. Do you believe in life after death, and why?
4. Do you like who you are now?
5. When was the last time you laughed so hard?
6. Would you relocate to a place where you don’t have any family or friends?
7. What secret trait do you wish that people know about you?
8. What is your personal philosophy in life?
9. Do you consider yourself spiritual or religious?
10. If all your wishes were granted today, how would you describe your life five years from now?
11. What is your worst memory of elementary school?
12. Are you close to your parents, and why?
13. Do you prefer looks or brains?
14. What is your best childhood memory?
15. What’s the one trait or personality you’d like to change about yourself?
16. Do you consider yourself an introvert or an extrovert?
17. What book and movie spoke to you, and in what way?
18. Are you assertive or a pushover?
19. What is your major turnoff in a romantic relationship?
20. Would you do a crazy thing for a friend?
21. Is your job now a reflection of what you said you wanted to be when you were a kid?
22. Do you believe that the present is really better than the past?
23. Have you seen an extreme example of poverty, and if so, how would you describe it?
24. What realities or truths are you in denial about?
25. Do you feel that you’re making a difference with the way you live your life?
26. Are you willing to share your password with your romantic partner, and why?
27. How do you feel about a cheating partner?
28. At what age do you think people should get married?
29. Do you think you will be a great parent, and why?
30. What would you do if your parents did not approve of your partner?
31. Do you believe that people of the opposite sex can be the best of friends?
32. Have you ever lost someone who’s very close to you?
33. Who is the person with whom you can talk about anything?
34. Do you believe in burning bridges when it comes to exes?
35. Do you prefer someone cheering you up, or being left alone when you’re in a foul mood?
36. How judgmental are you?
37. What is your description of a perfect weekend?
38. Have you broken someone’s heart recently?
39. Are you willing to relocate for love?
40. Do you keep a diary, and if yes, how often do you write in it?
41. What are the top five things you are grateful for?
42. Do you think that cheating partners should be given a second chance?
43. What do people constantly misunderstand about you?
44. How would you describe your perfect vacation?
45. What are the two greatest lessons you’ve learned from a past relationship?
46. Do you think that people can find true love online?
47. Do you regret anything in life?
48. What are three things that are on your bucket list?
49. What excites you the most?
50. When you’re alone, what do you usually think of?
51. How meaningful is your life?
52. What gives your life meaning?
53. What would your three wishes be if someone could make them come true?
54. Are you willing to lay down your life for someone, and who is it?
55. What top five lessons have you learned the hard way?
56. Do you believe in magic or in science?
57. What would the world be like if you hadn’t been born?
58. What is your definition of fame?
59. Do you wish to be famous?
60. What would you want to be famous for?
61. What is the greatest invention of this age?
62. Would you be willing to go the extra mile for something or someone?
63. Which one wins: reality or imagination?
64. When was the last time you said “I love you” to your parents?
65. Who do you look up to in life?
66. Do you give advice to others, and why?
67. Which is the better option: being a heartbreaker or being heartbroken?
68. If you could swap lives with someone for a day, who would you choose and why?
69. Which emotion best represents you, and why?
70. What do you think will bring about humanity’s extinction?
71. Do you feel happy when you use social media?
72. Will you encourage the younger generation to use social media?
73. If you had a billion dollars, how would you use the money to benefit the less privileged?
74. Which one is a better situation: broke or lonely?
75. When you die, would you prefer to be alone or surrounded by people you know?
76. What’s the lowest point in your life this year?
77. What’s the highest point you’ve experienced in your life this year?
78. Who’s hiding behind the mask you present to the world?
79. Is your life going in the direction you want?
80. If your life was a movie, what would the title be and why?
81. Have you experienced any miracle in your life?
82. Does art have any significance in society?
83. On a scale of 1 to 10, how fulfilled are you about life?
84. When was the last time you were moved to tears by a movie?
85. How do you define “a life well lived?”
86. What regrets would you have if you were to die today?
87. Can humans avoid being in love?
88. Is there such a thing as absolute freedom?
89. If you were given free rein to design the ideal metropolis, what would your city be like?
90. Is there such a thing as lasting peace?
91. Do you approve of stealing from the rich to give to the poor?
92. Do you believe that each one of us has a special mission in life?

100 Deep Questions to Ask Yourself

One of the benefits of answering deep questions is that you get the chance for self-reflection.

Self-reflection points out exactly where you are right now in your emotional landscape. It can also remind you about the goals you’ve set for yourself and force you to acknowledge whether you’re fulfilling them or not.

It would be a good idea to write down your answers in a journal.

1. Do I like who I am right now?
2. When was the last time I laughed so hard?
3. What would I truly regret not doing if I died tonight?
4. What advice has someone in my family given, and that I have taken just in time?
5. What were the top three lessons I learned the hard way?
6. What would I do if my biggest fear came true?
7. What would I do with my remaining days if I had only a year left to live?
8. Am I a servant of money, or does money serve me?
9. Why am I afraid of being true to myself when others are around?
10. What are the three things that I am most grateful for?
11. Have I done something recently that I could be proud of?
12. When was the last time I extended kindness to somebody?
13. What question do I want to know the answer to if it will help humanity?
14. What do I really want from life?
15. What aspect of my personality still needs improvement?
16. Must I take other people’s advice?
17. What annoys me the most?
18. Do others find me likable?
19. When was the last time I fell head over heels with life?
20. Am I enriching other people’s lives with what I do?
21. How meaningful is my life?
22. What makes life meaningful?
23. Would I lay down my life for somebody?
24. How much money would I be willing to give to those in need if I won the lottery?
25. The day that I would like to live over and over is _________________.
26. Am I worthy of being loved?
27. What talents or skills do I have that I can do better than anyone else?
28. What are the things that put me off?
29. My perception of fame is ________________________.
30. What is a peaceful life?
31. The most important aspect of a potential partner’s personality is ______________.
32. My greatest wish is _________________.
33. What am I most afraid of about life?
34. If I had not been born, what would be different about the world?
35. The three important lessons that I should have learned 10 years ago were: _______, __________, and ________?
36. If I could tell my 18-year-old self one thing, it would be _____________________.
37. If my life was made into a movie, the title would be ___________________.
38. Would I enjoy watching a movie made of my life?
39. Is my definition of success the same as everyone else’s?
40. Do I have a personal mission?
41. How would I describe the perfect day?
42. What am I willing to go the extra mile for?
43. What are my top five negative habits that I must change to something better?
44. Who do I look up to?
45. What outstanding qualities should my best friend have?
46. When was the last time I told someone I love him/her?
47. Am I satisfied with the quality of my romantic relationship?
48. When have I compromised my personal beliefs because I was afraid to be left out?
49. What skill do I possess that I can do better than others?
50. How often have I said yes when I wanted to say no?
51. What important lesson have I learned this week?
52. What three words would my friends use to describe me to strangers?
53. Have I intentionally broken someone’s heart?
54. Do I really listen when people talk to me?
55. What surprised me about myself this week?
56. How many hours have I been spending on the Internet?
57. Do I engage in negative self-talk?
58. Am I living a simple or complicated life?
59. How can I simplify my life?
60. Are there things that I should have done when I was younger that I can no longer do now?
61. What would I change if I were the most influential person in the world?
62. When was the last time I kept in touch with my family, and for how long was it?
63. When was the last time I tried something new?
64. What stresses me out the most?
65. How can I make my life easier?
66. When was the last time I gave something without expecting anything in return?
67. What is the most challenging experience I’ve overcome in the last five years?
68. Am I spending enough time doing the most important thing in my life?
69. What message can I share with the rest of the world?
70. How easily do I get discouraged?
71. What was it that I never told someone and still regret not telling them?
72. How assertive am I?
73. How old or young do I feel inside?
74. Do I resent others whenever I give in to their wishes?
75. What am I holding on to that I need to let go of?
76. If I were given an envelope containing the date of my death, would I open it?
77. Who among the people I know bring out the best in me?
78. Do I often make excuses?
79. What would I ask for if one of my wishes would come true?
80. Have I matured because of challenges or because of the enjoyable moments in my life?
81. Would I ever choose the easy way in life?
82. What’s standing between me and my greatest dream?
83. Where will I be five in years?
84. When was the last time I was furious?
85. What can I do to make a difference in people’s lives?
86. If failures are the best teachers, why is it so bad to fail?
87. Is it wrong to steal in order to feed a starving child?
88. What should I spend more time doing?
89. Am I missing someone today?
90. What mistake will I never make again?
91. How do I make the most out of life?
92. When was the last time I gave up on something that meant so much to me?
93. Who are the people I truly love, and what am I doing for them?
94. Do I ask questions, or am I content with what I know in life right now?
95. Would I be happy if I never had to work again?
96. Where do I find inspiration?
97. What can’t I live without?
98. Can I live without money, or without love?
99. When was the last time I lost track of time while doing something? What was that activity?
100. How do I want people to describe me at my funeral?

Bonus Round! A Few Questions to Ask Kids

While some of the above questions are deep and meant to spark a more meaningful conversation with someone, it is also always fun to talk to kids. Maybe they have a favorite movie they want to tell you about, or they have an embarrassing moment to share.

The following questions for kids are great conversation starters. They are interesting questions, funny questions, personal questions, and good questions to ask a younger audience.

1. Can you remember the last time you laughed so hard, you snorted?
2. How do you eat an Oreo?
3. What is your favorite letter of the alphabet?
4. Would you rather have to scream or whisper?
5. Do you have a favorite chore you like to help with around the house?
6. What is your favorite movie? Actor?
7. Would you visit the moon for one day if you could?
8. What is your perfect dessert?
9. Do you like board games? Which ones are your favorite?
10. When was the last time you had the best day ever?

Ready to Ask and Answer?

Well, that’s a wrap!

The answers to these questions will hopefully surprise, inspire, and move you.

Before we part, I’d like to leave you with this reminder.

In asking these deep get-to-know-you questions, there are two essential things to consider:

1. Your sincerity – Is your purpose for asking these questions truly to get to know the person better?
2. Your confidentiality – Some, if not most of the answers to these questions will be sensitive, and they will be given to you by the person in confidence. Remember to keep their answers private.

Hopefully you picked up a few great questions to ask during your next conversation, and hopefully, the responses will help you build a deeper connection with someone.

​​Finally, asking deep questions and improving the quality of your conversations is skill that can be developed -- if you treat it like a habit.  So if you'd like to learn how to build simple, daily habits that will help your ​relationship goals, then I suggest checking out this book, which has 127 small changes to improve your health, wealth, and happiness.​