Personal Development

371 Deep Questions to Ask Someone [Updated for 2023]

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One of the best ways to get to know someone better is by asking open-ended, deep 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.

For a quick example simply asking someone what their favorite childhood memory is can give you an idea of their values, what shaped their lives and what matters to them.

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 can help us deepen our understanding of life, purpose and ourselves. What would it take to truly fulfill you and realize your purpose in life?

Do you regret the time you broke someone’s heart? What’s the perfect vacation that could help set your mind and heart free?

Thinking through such questions can bring new perspectives that could lead to improved decision making and self-discovery. They may be difficult to answer, but if we take the opportunity to explore them, they can open up possibilities and provide nourishment for meaningful life.

So with that in mind, this post contains 371 deep questions that will help you:

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)

Also, ​If you want to use deep questions to spark the interest of someone you’re interested in, then you should also check out these two resources: For guys, there are 3 text message that can get a girl interested in you. And for girls, there is a concept known as a “devotion sequence” that can attract the long-term interest of a guy.

Remember that although these questions, like this or that 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 to the questions you can ask someone…

91 Deep Questions to Ask a Girl

Asking a girl deep questions is a great way to break the ice and find out more about a girl you are interested in getting to know a little bit better.

These deep questions will help keep a conversation going, deepen your understanding of her, and open new doors for potential topics of discussion.

(Here’s an 11-step process on keep a conversation going)

Asking about her thoughts on when she broke someone’s heart or last time she had her heart broken, will reveal give great insights into her views on relationships.

Questions about her experience with long distance relationships can uncover similar values and interests that you two may share. It is also important to ask her thoughts on the opposite sex and how she views the idea of soul mates.

These questions will help prevent any surprises down the road by acting as relationship deal breaker that can create openness in your interactions.

deep questions to ask a girl to help you discover the things she values the most
  1. If you were given three things to make you happy, what would these be?
  2. What has been the biggest lesson you’ve learned from a past relationship?
  3. How would you rank the following in importance: family, career, love life?
  4. Do you believe in soulmates or multiple loves throughout life?
  5. Which would you prefer: having a baby without a partner or a partner without a baby?
  6. Are there any beliefs that guide or shape your morals and values system?
  7. Have you ever broken someones heart? What happened?
  8. If you could teach one thing to the opposite sex, what would it be?
  9. What was your experience about being “mansplained,” and what did you do about it?
  10. What is your biggest fear and how have you tried to overcome it?
  11. Who was your favorite cartoon character when you were a kid?
  12. Do you think God is real, and why?
  13. Have you ever had your heart broken?
  14. Do you believe in giving people second chances, and why?
  15. How would you describe your first crush?
  16. How do you define success for yourself?
  17. Do you ever keep a journal?
  18. 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)?
  19. How do you feel about the #MeToo movement?
  20. What do you look for in a relationship?
  21. What is your idea of a perfect date?
  22. What legacy do you want people to remember about you after you’re gone?
  23. Have you ever asked a guy out on a date?
  24. What was the most important lesson you’ve learned from your past relationship?
  25. What book influenced you the most?
  26. What life-changing event have you experienced?
  27. What’s a deal-breaker for you in a relationship?
  28. Are you a morning or a night person?
  29. How important is trust in a relationship?
  30. How do you feel about infidelity?
  31. Do you believe that the day will arrive when humans will be replaced by machines in almost all aspects of life?
  32. What do you think is humankind’s greatest invention?
  33. Do you think that humans are doing more harm than good to the planet?
  34. What is your take on telepathy?
  35. What is your favorite workout routine?  (Here are 51 options)
  36. Would you rather be called vain or insecure?
  37. What important lesson did a close relative teach you?
  38. What part of your body do you find attractive?
  39. Which would you choose to be: law-abiding citizen or rule breaker, and why?
  40. What is your ideal vacation?
  41. What superpowers did you wish you had when you were a kid?
  42. Are you a mountain or a beach person?
  43. What mythical animal do you resonate with, and why?
  44. Which member of your family do you feel closest to, and why?
  45. Who do you consider your best friend in your workplace?
  46. What three adjectives would describe you?
  47. If you could live anywhere in the world, where would you choose?
  48. What are you passionate about in life?
  49. What quality in a person do you fall in love with?
  50. Have you had your heart broken before?
  51. What is your take on astrology?
  52. What is your life’s soundtrack? Or what type of music inspires you?
  53. When was the last time you spoke with a classmate from high school?
  54. Are you left- or right-handed, and would you want to switch?
  55. What subject were you good at in high school?
  56. What was the most memorable experience you had in elementary school?
  57. Do you find it difficult to admit that you are wrong, and why?
  58. Do you get excited or scared when meeting new people?
  59. What is your secret hobby that others would consider weird?
  60. How do you cope with stressful situations?
  61. Is there anything that you would like to change about yourself?
  62. What musical instrument do you know how to play?
  63. Who or what inspires you?
  64. Which would you prefer in a romantic partner: a dreamer or an achiever?
  65. What is your favorite part of a house, and why?
  66. Who is the fictional character who closely resembles you in terms of attitude?
  67. When you were a kid, what did you say you wanted to be when you grew up?
  68. What was the title of the first movie you watched in a movie theater?
  69. When was the last time you slept outdoors?
  70. What is something that you are proud of about yourself?
  71. What song do you often sing in the shower?
  72. What do you feel is the right age for people to get married?
  73. What would be your super villain name and your powers?
  74. What three non-electric or non-automatic items would you take on a deserted island?
  75. If “hello” were to be replaced by another word as a greeting, what word would that be?
  76. What is the weirdest thing that your family does together?
  77. What was the most embarrassing thing that you’ve done for a friend?
  78. What task would you really fail at doing?
  79. What is your definition of a “perfect life”?
  80. What would be the title of the movie showing your life from birth up to present?
  81. What fashion piece would you invent for women?
  82. What is the single most important thing people should do for the planet?
  83. How do you define evil, and do you believe that a person can be evil?
  84. What do you think are the two things that prevent people from realizing their dreams?
  85. Would you lay down your life for someone?
  86. What word or term do you wish to know the meaning of?
  87. What makes you nostalgic?
  88. Do you believe that each of us has a soul mate?
  89. How would you live your remaining days if you found out you had only a week to live?
  90. Do you listen to other people’s advice, or do you prefer figuring things out yourself?
  91. What is your favorite motivational quote?
  92. Imagine that you are tasked to re-design society – what changes would you make?
  93. What’s the perfect day for you?
  94. What is one thing that make life worth living for you?
  95. Would you wait for the sun to rise or for it to set, and why?
  96. If you were born in another era, when would that period in history be and why?
  97. Have you made someone cry?
  98. What was the last dream (nightmare/daydream) that stood out to you recently and why did it affect you so much ?
  99. What is the most astonishing act that a person can do for you?
  100. 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?
  101. Who are some people in your life who inspire and motivate you grow both personally and professionally?
  102. If you die tonight, would you pass away fulfilled or unsatisfied with life?

90 Deep Questions to Ask a Guy

If you’re looking to keep the conversation going with a guy, don’t forget to ask the deep questions.

It can be easy to get caught up in those small talk conversations with surface-level topics. Instead, try to dig deeper and get beyond the basic getting-to-know-you questions.

Ask him about his most cherished relationships, if he would ever consider long distance relationships as an option, or what his relationship deal breaker is.

Not only will this keep the conversation going but also help you both understand each other on a deeper level.

Ask these deep questions to help you understand the guys capacity for humor and his overall character and attitude.
  1. What has been your most significant takeaway from a past relationship?
  2. How would you describe the perfect day?
  3. Is there any decision that you feel guilty about making in your personal life?
  4. If you could describe yourself in three words, what would they be?
  5. What is one guilty pleasure that makes you smile when no one’s looking?
  6. How have you grown as an individual since meeting your best friend?
  7. Do you believe in fate or destiny and why/why not?
  8. What movie influenced you the most?
  9. At what age do you think people should think of settling down?
  10. If you were stranded on a deserted island, what three items that are not electronic or automatic would you take with you?
  11. What is the weirdest thing that fascinates or intrigues you about the world we live in?
  12. What’s the one thing that has been your biggest pet peeve in a relationship?
  13. How do you follow your gut feeling when it comes to making important decisions?
  14. What is your guilty pleasure that makes you smile even when nobody else does?
  15. Do you believe in soul mates and why/why not?
  16. What are some of your favorite songs and why do they mean so much to you?
  17. What is your favorite hobby and what keeps drawing you back to it?
  18. Are there any bad habits that hold you back from achieving success in life or relationships ?
  19. If given complete freedom, how would one day look like for an ideal version of yourself ?
  20. Can regret ever lead to positive growth and if so, how ?
  21. In moments of doubt, what helps bring clarity back into focus for you ?
  22. If they made a movie about your life, who would you choose as the director and why?
  23. What ability do you possess that you’d think others would find amazing?
  24. Have you ever stayed up all night to wait for sunrise?
  25. When was the last time you slept under the stars?
  26. Would you rather be a world-famous pro-MMA athlete or the president of a country?
  27. What do you think are the essential components of a healthy relationship?
  28. Can you remember the last time you cried, and what was the reason?
  29. Who do you feel is your closest confidant among your family members?
  30. If you were given a million dollars today, how would you spend it within three days?
  31. Do you have a favorite memory that has made an impact on how you see things now?
  32. What two items would you need to survive an apocalyptic zombie invasion.
  33. When you were growing up, which superhero was your favorite, and why?
  34. What is your funniest memory of high school?
  35. How would you spend your remaining time if you found out you only had 10 days left to live?
  36. What’s one item you’ve recently crossed off your bucket list?
  37. Do you have a favorite place in the world, and where is it?
  38. Are you a cat or a dog person, and why?
  39. Are you more afraid of failure or success, and why?
  40. What was your most memorable birthday?
  41. At what age did you have your first pet, and what was it?
  42. What things or situations make you feel unsure about yourself?
  43. What do you feel is your greatest accomplishment to date?
  44. What would you do for the people you love?
  45. At this point in your life, what is it that you wish your family knew about you?
  46. When was the last time you said “I love you” to someone?
  47. If you have to lay your life on the line for someone, who would that person be?
  48. Do you believe in fate, or do you think that things happen because of our decisions?
  49. What period of history would you change if given the chance?
  50. Who is your real-life hero?
  51. What was it like growing up in your hometown?
  52. If you were to give up one of your senses, what would it be?What was your most embarrassing experience at work?
  53. Are you a leftie or right-handed, and would you be willing to switch?
  54. How would people close to you describe you in three words?
  55. What skill do you envy in other people?
  56. What is your pet peeve in the workplace?
  57. What is your view about monogamy?
  58. Have you ever broken someone’s heart?
  59. What was your biggest “facepalm” moment?
  60. How happy are you right now?
  61. What was the most embarrassing thing that you did for someone you love?
  62. Have you experienced losing someone you care a lot about?
  63. If you were offered an all-expense-paid plastic surgery, would you accept it, and what would you change about your physical appearance?
  64. Are you a dreamer or a go-getter?
  65. What important lesson have you learned from a family member?
  66. Do you agree that people never change, they just show their true colors?
  67. How do you wish people will remember you after you’re gone?
  68. What qualities are you looking for in a partner?
  69. Are humans fueled by greed or by love?
  70. What, for you, is the ultimate comfort food?
  71. Have you ever had a brush with death?
  72. If you were in a band, what instrument would you play?
  73. If you were given a chance to swap places with somebody for a day, who would you choose?
  74. Do you like your given name, and why or why not?
  75. Are you afraid of dying?
  76. Do you have a life’s purpose, and what is it?
  77. Is there somebody you would consider “the one who got away”?
  78. Do you see the glass as half-full or half-empty? (Sidebar: If you are a negative person, then these 37 strategies can help.)
  79. What is that one thing other people do that you find amusing?
  80. If you were given the chance to live anywhere in the world, where would you stay?
  81. How do you cope when things are not going your way?
  82. Is there a film or cartoon character who is very much like you? In what way?
  83. Which of your habits would other people consider weird?
  84. What is your biggest turn-off in a relationship?
  85. Do you believe we make our own happy endings, or is fate responsible for them?
  86. What long-held belief did you have that was recently disproved by science?
  87. What was your most memorable adventure when you were 10 years old?
  88. Is there any part of your personality that you feel you need to improve? If so, which part and why?
  89. What is the most awkward situation you’ve experienced recently?
  90. If there were a universal way of greeting, what should it be?
  91. In what manner do you think you will die?
  92. As a force, are we humans creative or destructive?
  93. Why do you think people believe in conspiracy theories?
  94. How would you describe honor?
  95. What is the value of art in society?
  96. Can the world really achieve lasting peace?
  97. Do you think that some lives are more precious than others?
  98. What is the perfect life for you?
  99. Do you believe that the day will come when computers will be more intelligent than humans?
  100. How will our civilization go extinct?
  101. Is happiness a state of mind or we need to act in order to achieve it?
  102. How do you rank these three according to importance: career, family, love?
  103. How real is God?
  104. Was there a book that influenced you the most?
  105. What do you regret doing in life?
  106. What are you most proud of in your life?
  107. If you were to die tonight, would you die as a fulfilled or an unsatisfied person?

(If you want more questions to ask your partner, here’s a list of 43 questions that can start a deep conversation.)

92 Deep Questions to Ask Your Friends

With deep questions to ask your friends, you can keep the conversation going in any setting.

Whether it’s public or private, over coffee or a text message, exploring meaningful topics can keep your conversations from going stale.

Try to step outside of the entire world and put yourself in the shoes of a genie; if they were to grant you one wish when it comes to your friendship with someone, what would that be? What is the most important phase in this person’s life right now?

Working through these good questions that will follow will help keep the conversation lively and engaging and help to get you know someone on a deeper level.

Try out these questions to get to know someone and deep questions to ask your friends to help you gauge their intelligence and learn about their level of compassion. #friendship #friendshipquotes #friendshipgoals #questions #dating #datingtips #relationshipadvice #conversation
  1. If you died tonight, what would you regret not doing?
  2. What will people say about you at your funeral?
  3. What are some favorite songs that have impacted your life, and why?
  4. What do you consider to be your biggest mistake in life so far?
  5. How have your best friends influenced you throughout your life?
  6. Where was the best birthday celebration you ever had and what made it special?
  7. If money were no object, how would an ideal weekend look for you?
  8. What’s the most spontaneous thing you’ve ever done and why did you choose to do it at that moment ?
  9. What was the worst phase of your adult-life so far, and how did get through it ?
  10. If a crystal ball could predict anything about yourself 10 years from now, what would surprise or excite you ?
  11. What’s one challenge that shaped who are today more than any other ?
  12. Do you believe in life after death, and why?
  13. Do you like who you are now?
  14. When was the last time you laughed so hard?
  15. Would you relocate to a place where you don’t have any family or friends?
  16. What secret trait do you wish that people know about you?
  17. What is your personal philosophy in life?
  18. Do you consider yourself spiritual or religious?
  19. If all your wishes were granted today, how would you describe your life five years from now?
  20. What is your worst memory of elementary school?
  21. Are you close to your parents, and why?
  22. Do you prefer looks or brains?
  23. What is your best childhood memory?
  24. What’s the one trait or personality you’d like to change about yourself?
  25. Do you consider yourself an introvert or an extrovert?
  26. What is your favorite book and why?
  27. Do you consider yourself an introvert or an extrovert?
  28. What is your fondest childhood memory?
  29. If you could have dinner with any five people, alive or deceased, who would they be and why?
  30. Would you rather travel the world for a year, or stay in one place for three years to build a business from scratch?
  31. What are some of the best things that make you feel alive and happy?
  32. Is your job now a reflection of what you said you wanted to be when you were a kid?
  33. Do you believe that the present is really better than the past?
  34. Have you seen an extreme example of poverty, and if so, how would you describe it?
  35. What realities or truths are you in denial about?
  36. Do you feel that you’re making a difference with the way you live your life?
  37. Are you willing to share your password with your romantic partner, and why?
  38. How do you feel about a cheating partner?
  39. At what age do you think people should get married?
  40. Do you think you will be a great parent, and why?
  41. What would you do if your parents did not approve of your partner?
  42. Do you believe that people of the opposite sex can be the best of friends?
  43. Have you ever lost someone who’s very close to you?
  44. Who is the person with whom you can talk about anything?
  45. Do you believe in burning bridges when it comes to exes?
  46. Do you prefer someone cheering you up, or being left alone when you’re in a foul mood?
  47. How judgmental are you?
  48. What is your description of a perfect weekend?
  49. Have you broken someone’s heart recently?
  50. Are you willing to relocate for love?
  51. Do you keep a journal, and if yes, how often do you write in it?
  52. What are the top five things you are grateful for? (Here are 155 gratitude prompts you can use during this type of conversation.)
  53. Do you think that cheating partners should be given a second chance?
  54. What do people constantly misunderstand about you?
  55. How would you describe your perfect vacation?
  56. What are the two greatest lessons you’ve learned from a past relationship?
  57. Do you think that people can find true love online?
  58. Do you regret anything in life?
  59. What are three things that are on your bucket list?
  60. What excites you the most?
  61. When you’re alone, what do you usually think of?
  62. What gives your life meaning?
  63. What would your three wishes be if someone could make them come true?
  64. Are you willing to lay down your life for someone, and who is it?
  65. What top five lessons have you learned the hard way?
  66. Do you believe in magic or in science?
  67. What would the world be like if you hadn’t been born?
  68. Do you wish to be famous?
  69. What would you want to be famous for?
  70. What is the greatest invention of this age?
  71. Would you be willing to go the extra mile for something or someone?
  72. Which one wins: reality or imagination?
  73. When was the last time you said “I love you” to your parents?
  74. Who do you look up to in life?
  75. Do you give advice to others, and why?
  76. Which is the better option: being a heartbreaker or being heartbroken?
  77. If you could swap lives with someone for a day, who would you choose and why?
  78. Which emotion best represents you, and why?
  79. What do you think will bring about humanity’s extinction?
  80. Do you feel happy when you use social media?
  81. Will you encourage the younger generation to use social media?
  82. If you had a billion dollars, how would you use the money to benefit the less privileged?
  83. Which one is a better situation: broke or lonely?
  84. When you die, would you prefer to be alone or surrounded by people you know?
  85. What’s the lowest point in your life this year?
  86. What’s the highest point you’ve experienced in your life this year?
  87. Who’s hiding behind the mask you present to the world?
  88. Is your life going in the direction you want?
  89. If your life was a movie, what would the title be and why?
  90. Have you experienced any miracle in your life?
  91. Does art have any significance in society?
  92. On a scale of 1 to 10, how fulfilled are you about life?
  93. When was the last time you were moved to tears by a movie?
  94. How do you define “a life well lived?”
  95. What regrets would you have if you were to die today?
  96. Can humans avoid being in love?
  97. Is there such a thing as absolute freedom?
  98. If you were given free rein to design the ideal metropolis, what would your city be like?
  99. Is there such a thing as lasting peace?
  100. Do you approve of stealing from the rich to give to the poor?
  101. Do you believe that each one of us has a special mission in life?

100 Deep Questions to Ask Yourself

Have you ever asked yourself a question so deep that it makes you feel uneasy?

Asking yourself good questions on a deeper level can lead to valuable self-reflection. The truth is, the more uncomfortable questions you ask yourself, the more insights that can be gained.

Certain topics may seem daunting at first but opening your mind to thought-provoking ideas can help get past those mental blocks and take your personal growth to the next level.

Good questions are like stepping stones – they enable us to reach new levels of understanding ourselves, our surroundings and our relationships with others. So don’t be afraid to ask yourself the tough questions – it’s time to embark on a thoughtful quest through self-discovery and personal growth!

(Also, if you want to understand yourself on a deeper level, then you might want to try journaling. Here is a step-by-step process on how to build the journaling habit.)

Check out these deep questions to ask yourself as journal prompts so you can understand yourself better. #journal #journaling #personaldevelopment #personalgrowth #mindset #selfimprovement #inspiration #motivation #success #learning
  1. Do I like who I am right now?
  2. Would you rather take a risk that could change your life for the better, or stay comfortable in your current situation?
  3. What makes you feel most alive and passionate about life?
  4. What is your favorite childhood memory and why?
  5. What is the craziest thing you have ever done and why did you do it?
  6. If you could save one person in the entire world, who would it be and why?
  7. What is your biggest fear, and how has facing it helped shape who you are today?
  8. When was the last time I laughed so hard?
  9. What would I truly regret not doing if I died tonight?
  10. What advice has someone in my family given, and that I have taken just in time?
  11. What were the top three lessons I learned the hard way?
  12. What makes you feel most alive and passionate about life?
  13. Who was your favorite teacher and why?
  14. What meaningful conversations have had the biggest impact on you so far in life?
  15. What is your guilty pleasure that puts a smile on your face even when nobody else does?
  16. How do you follow your gut feeling when it comes to making important decisions?
  17. If money were no object, what would be one thing that would make every day more enjoyable for yourself?
  18. What would I do if my biggest fear came true?
  19. What would I do with my remaining days if I had only a year left to live?
  20. Am I a servant of money, or does money serve me?
  21. Why am I afraid of being true to myself when others are around?
  22. What are the three things that I am most grateful for?
  23. Have I done something recently that I could be proud of?
  24. When was the last time I extended kindness to somebody?
  25. What question do I want to know the answer to if it will help humanity?
  26. What do I really want from life?
  27. What aspect of my personality still needs improvement?
  28. Must I take other people’s advice?
  29. What annoys me the most?
  30. Do others find me likeable? (These social habits can make you more likeable.)
  31. When was the last time I fell head over heels with life?
  32. Am I enriching other people’s lives with what I do?
  33. How meaningful is my life?
  34. What makes life meaningful?
  35. If you died tomorrow, what would be the one thing that you wish you could have done?
  36. Would you rather explore outer space or stay on Earth and continue living life as normal?
  37. What is your favorite thing about yourself that has stayed consistent throughout this past year?
  38. Are there any religious or spiritual beliefs that bring comfort to difficult times in life?
  39. How would spending time with your closest family members change if money was no object?
  40. What advice from a trusted mentor has had the most impact on how you live today ?
  41. Would I lay down my life for somebody?
  42. How much money would I be willing to give to those in need if I won the lottery?
  43. The day that I would like to live over and over is _________________.
  44. Am I worthy of being loved?
  45. What talents or skills do I have that I can do better than anyone else?
  46. What are the things that put me off?
  47. My perception of fame is ________________________.
  48. What is a peaceful life?
  49. The most important aspect of a potential partner’s personality is ______________.
  50. My greatest wish is _________________.
  51. What am I most afraid of about life?
  52. If I had not been born, what would be different about the world?
  53. The three important lessons that I should have learned 10 years ago were: _______, __________, and ________?
  54. If I could tell my 18-year-old self one thing, it would be _____________________.
  55. If my life was made into a movie, the title would be ___________________.
  56. Would I enjoy watching a movie made of my life?
  57. Is my definition of success the same as everyone else’s?
  58. Do I have a personal mission?
  59. How would I describe the perfect day?
  60. What am I willing to go the extra mile for?
  61. What are my top five negative habits that I must change to something better?
  62. Who do I look up to?
  63. What outstanding qualities should my best friend have?
  64. When was the last time I told someone I love him/her?
  65. Am I satisfied with the quality of my romantic relationship?
  66. When have I compromised my personal beliefs because I was afraid to be left out?
  67. What skill do I possess that I can do better than others?
  68. How often have I said yes when I wanted to say no?
  69. What important lesson have I learned this week?
  70. What three words would my friends use to describe me to strangers?
  71. Have I intentionally broken someone’s heart?
  72. Do I really listen when people talk to me?
  73. What surprised me about myself this week?
  74. How many hours have I been spending on the Internet?
  75. Do I engage in negative self-talk?
  76. Am I living a simple or complicated life?
  77. How can I simplify my life?
  78. Are there things that I should have done when I was younger that I can no longer do now?
  79. What would I change if I were the most influential person in the world?
  80. When was the last time I kept in touch with my family, and for how long was it?
  81. When was the last time I tried something new?
  82. What stresses me out the most?
  83. How can I make my life easier?
  84. When was the last time I gave something without expecting anything in return?
  85. What is the most challenging experience I’ve overcome in the last five years?
  86. Am I spending enough time doing the most important thing in my life?
  87. What message can I share with the rest of the world?
  88. How easily do I get discouraged?
  89. What was it that I never told someone and still regret not telling them?
  90. How assertive am I?
  91. How old or young do I feel inside?
  92. Do I resent others whenever I give in to their wishes?
  93. What am I holding on to that I need to let go of?
  94. If I were given an envelope containing the date of my death, would I open it?
  95. Who among the people I know bring out the best in me?
  96. Do I often make excuses?
  97. What would I ask for if one of my wishes would come true?
  98. Have I matured because of challenges or because of the enjoyable moments in my life?
  99. Would I ever choose the easy way in life?
  100. What’s standing between me and my greatest dream?
  101. Where will I be five in years?
  102. When was the last time I was furious?
  103. What can I do to make a difference in people’s lives?
  104. If failures are the best teachers, why is it so bad to fail?
  105. Is it wrong to steal in order to feed a starving child?
  106. What should I spend more time doing?
  107. Am I missing someone today?
  108. What mistake will I never make again?
  109. How do I make the most out of life?
  110. When was the last time I gave up on something that meant so much to me?
  111. Who are the people I truly love, and what am I doing for them?
  112. What is your idea of a perfect day?
  113. If you could be someone else for 24 hours, who would you be and why?
  114. What was the most beautiful thing you have ever seen in nature?
  115. How does it make you feel when someone looks at you with admiration?
  116. Describe what it felt like the first time that something made sense to you.
  117. What do you think is the best way to show gratitude towards those around us?
  118. Do I ask questions, or am I content with what I know in life right now?
  119. Would I be happy if I never had to work again?
  120. Where do I find inspiration?
  121. What can’t I live without?
  122. Can I live without money, or without love?
  123. When was the last time I lost track of time while doing something?

(Bonus): Deep 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.

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

Final Thoughts on These Deep Questions to Ask Someone

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 best deep 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 questions to get to ask during your next conversation, and hopefully, the responses will help you build a deeper connection with someone.

And if you’re looking for more good questions, then we have a many similar articles that will help you with asking deep questions to learn more about yourself and others.

For instance, if you’re in a committed relationship (or want to be in one), you should check out these articles:

Or perhaps you’re looking to spend some quality time with your children, then this article offers some clean and fun 125 “would you rather questions” for them to answer.

And if you’re looking for more introspective questions, here’s a list of 101 questions to ask yourself to find out who you are.

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.

Check out these 371 deep questions to help you get answers to reveal a person’s true character.

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