300+ Deep Questions to Ask

Most of the times we are caught in situations when we want to know the personal facts about our friends and loved ones. Such facts are related to the likes and dislikes of our loved ones and some other important information which is vital to stay in the relationship. Deep questions to ask someone are a must these days as you have to know the person completely without any doubts. Compatibility is one of the vital things that people are always looking in the relationship because this is the connecting feature to an intellectual level. However, the compatibility is not that important for all of the people but certainly it is the important to make it sure you are having a great time with the person you like.

Will in case if you are eager to know about the girl or guy with whom you want to spend your entire life or interested in somebody to make her/him best friend. Then you have to go for asking them deep questions which will let you know the secrets of their lives. You will find out some basic and important secrets of their lives if you would deep questions to ask friends. However, the questions might be sounding funny at the beginning but it will affect the person mentally to whom you would ask and in return they would tell you the truth. Through deep questions to ask you can solve the mysteries regarding your friends which you have been trying to solve from years.

There are numerous ways of test the compatibility and one of the main purpose is through deep questions to ask. You can ask the deep questions from your friends, family members, and the ones with whom you want to have an everlasting relationship. Deep questions will let you know to how extent you are connected to your friend and loved ones. The following are some of the top deep questions to ask boyfriend and deep questions to ask girlfriend.

List of Deep Questions to ask Guys and Girls

  1. On which philosophy you are believing and acting in your life?
  2. What are the things which you would like to change in your life about yourself?
  3. Do you have any regrets in life?
  4. Are you happy being my friend?
  5. Do you have spiritual or religious beliefs and why?
  6. Will you like to consider yourself an extrovert or introvert person and why?
  7. Are you close to your mother or father and why?
  8. Do you have any phase in life which is best for you and will never forget it?
  9. With whom you like to spend your time and why?
  10. What was the worst phase of your life and what made it worse?
  11. What you have been dreaming to do since childhood and is that the thing what you always wanted what you do today?
  12. What are the facts and things which makes you feel accomplished in life?
  13. What is the name of your favorite movie and how often do you speak of it?
  14. What are the relationship breaker facts for you?
  15. What do you prefer more brains or looks?
  16. Will you ever give a second chance to a person who has cheated on you?
  17. Will you share the passwords of your gadgets with your partner or girlfriend / boyfriend?
  18. What is the perfect time to get married in your thinking?
  19. What do you think what kind of parent you would become, either friendly or aggressive?
  20. What is the name of your favorite book and how often do you speak of it?
  21. At what age do you think a person should get married?
  22. What will you do if your parents will not like the person whom you choose as a partner?
  23. Who is the person in your life to whom you can share anything in life?
  24. Are you staying friends with your exes or you just cut off each relation with them?
  25. Have you ever lost someone who is close to your heart?
  26. When you are angry or in bad mood, what do you like to do, either want to be left alone or like to talk to someone who make you cheer?
  27. What is the ideal weekend for which you are yet waiting?
  28. Who can be best friends in opposite sex for you?
  29. Are you a person who judge a book by its cover or you prefer reading it?
  30. Are you a confrontational person?
  31. How long it passed until you have broken someone’s heart?
  32. Would you like to relocate for your love or you would like her / him to relocate for you?
  33. Did you ever try to write in some journal?
  34. Is there any person in life to whom you are thankful the most?
  35. Do you have any belief in second chance in life?
  36. Are there any facts due to which people are misunderstanding you or they get you in a negative way?
  37. Do you have any desire or idea of a perfect vacation to some place/
  38. What you have learnt the most from your past relationships?
  39. Are you in to the online relationships either through tinder or any other website?
  40. What are the things on your bucket list this year?
  41. What is your New Year resolution?
  42. When have you felt your biggest adrenaline rush?
  43. What are the craziest things that you have done in your life and will you do it again if you ever get a chance?
  44. What would be the three wishes if ever a genie ask you to fulfill?
  45. What do you think of yourself when you are all alone

Very Hard Deep Questions to ask friends

The following are some hard questions that you can ask your friend and make the moments precious by knowing about them.

  1. What is the most important problem that you have ever wanted to fix in your life?
  2. Have you ever a wish to live in an era which is not familiar to you?
  3. What will be the top advice that you would give to a person who is about to get graduate from the high school?
  4. What will be the name to yourself, if you have ever a chance to pick by yourself?
  5. If your home is set on a fire and you are having only three things to save your house, what would be the three things?
  6. If you ever get fame in your life, would you be enjoying the limelight given to you or you will miss your privacy?
  7. What you will buy for me if you have $500 to spend?
  8. If you are asked that three of your wishes would be accepted and granted, name the three wishes?
  9. If you get a news that you are having a terminal illness, how would you react to such news?
  10. What will be the things to do if you are having only a few weeks to live and will you like to share these moments to anyone?
  11. Will you like to sacrifice your life for someone whom you don’t know and will never know?
  12. Will you sacrifice your life for your exes?
  13. Will you like to give away or donate your kidney to your family member or your exes if you are the only match?
  14. If you are supposed to gift me a puppy, will you like to adopt it for me from a pure bred or you will go for a mix bred from some shelter?
  15. If you have ever suspected that your neighbors are abusing your child, will you call the police or settle the matters with your own way?
  16. Suppose, if I am missing and I am not discovered for a week, would you devote your life in searching for me or you would wait for some more days and forget me forever?
  17. Who will be the three people that you would invite for a dinner if you have a chance?
  18. If you have to live till the age of 100 years, would you like to have the mind or body of 25 years old person, and why?
  19. What do you think a powerful mind or powerful body is necessary for a 50 years old person and why?
  20. If you have gained a special ability when you wake up the next morning, what ability would you like to gain and why?
  21. If you have a ball which can tell you about a person’s life, future, or anything that you desire off, then what you will choose and why?
  22. What is the dream place where you would like to stay forever?
  23. How long you have been doing wrong things with sleepy people?
  24. Have you ever took advantage of someone’s trust?
  25. Have you ever mislead any person throughout your life?

Some Personal Deep Questions to ask someone whom you want to Know Better

The following are some important deep questions to ask girlfriend and some deep questions to ask boyfriend.

  1. Which option would you like to have either living for a moment or to be a slave for your life?
  2. What is thing which you love the most about yourself?
  3. What would you like to change in yourself if you ever get a chance to do so?
  4. Which do you like the most? Going out for fun or living alone?
  5. Are you considering yourself and inner motivated person or an externally motivated person?
  6. If you ever come across failure? How are you catering failure?
  7. To whom you give more importance, to the people around you or the things which you do around yourself?
  8. When you are having your things broken, do you prefer to replace them or to fix them and reuse?
  9. Are you a materialistic person or not?
  10. What is a perfect day according to your definition?
  11. Where would you like to have your date night?
  12. What is the perfect date night as per your definition?
  13. What are the things that are offending you the most?
  14. What is the only thing without which you are not able to start your day?
  15. What is helping you to wind down yourself when you are stressed or freaked out?
  16. What would you like people doing with your corpse when you will be dead either burying or burning?
  17. What is the most inspiring thing for you?
  18. Have you ever got inspired from any saint?
  19. Are you realistic, optimistic, or pessimistic person and why?
  20. We notice an old man living out of a shopping cart behind a grocery store. What is your first thought about him?
  21. If someone is calling me something that is too horrible. What would be the first thing that you would do either letting him / her doing horrible things or defend me with all powers you have?
  22. Do you think having female friends at work is okay or is it a bad thing to do?
  23. Do you like having friends with benefits?
  24. Do you ever wish to sleep with your best friend?
  25. What are three things you are willing to splurge on for yourself?
  26. Have you ever rehearsed a phone call before actually calling the person?
  27. Have you ever made anyone cum on phone call?
  28. When was the last time when you sang in front of a mirror for yourself?
  29. What are you most thankful for?
  30. Have you ever fooled anyone on phone call on 1st April i.e. fool day?
  31. What are the things that you have always dreamt of but could not do until yet?
  32. Have you ever tried to achieve something that is illegal?
  33. Have you ever caught in fear of becoming old?
  34. Have you ever cheated on your girlfriend / boyfriend?
  35. Is there any instance in your life which made you frightened to drive a car?

Deep Questions to Ask about Past of your Friends

The following are some of most important questions that are necessary to ask to know about the past of your friends.

  1. Have you done something in past which made you regret over it?
  2. What is the status of yourself that you see after 5 years?
  3. What is happiest memory of your life?
  4. What was the last time when you were shedding tears?
  5. What is a tradition you did as a child that you want to do with your kids someday?
  6. What are the few things that you have earned in the hard way in your life?
  7. What are the dreams in your life that you can recall vividly till date?
  8. What are the aspirations in your life that have never changed?
  9. What are the aspirations in your life that have been changing with passing time?
  10. What do you see yourself when you will become 60 years old?
  11. What is the terrible memory of your life?
  12. In which way have you changed in life since your childhood?
  13. What are the aspects in which you would like to change yourself?
  14. At what age you were in love for the first time?
  15. Who was your first crush in life?
  16. At what age first you said I love you to anyone?
  17. Have you ever got an inspiration from any book that has an impact on your life?
  18. What insecurity you have in life?
  19. Have you ever been insecure of anyone in your life?
  20. Have you ever ashamed of your act?
  21. Is there anything in your life that you cannot share with your family members?
  22. At what age you first had sex?
  23. Have you been homosexual in any phase of your life?
  24. What are the things that you will like to change in your past?
  25. Who is the most inspirational personality for you in your past?

Deep Questions to ask your Boyfriend in Political Scenarios

The following are some major questions that you would like to ask your friends and loved ones about the political atmosphere in your nearby.

  1. Have you ever liked Donald Trump?
  2. What is your political affiliation?
  3. What is the biggest flaw in the welfare system as per your understanding?
  4. Why is the rate of divorce getting too high as per your understanding?
  5. If you will ever run the campaign for presidency, what will be the key factors at which you would stress on?
  6. What you are either pro-choice or pro-life?
  7. Do you like the genetically modified food or not?
  8. Do you think the food may be modified genetically or not?
  9. What are the key factors which can make a small business successful?
  10. What inventions have demolished the mankind?
  11. What inventions have fuel the mankind on the way of prosperity?
  12. Should teen agers be allowed to have cell phones or not?
  13. Are you proud to be resident of the country?
  14. How important is school in one’s life as per your views?
  15. Is person’s outward appearance says or reflect anything about the personality of the person?
  16. Is the current president of the country in favor of the welfare?
  17. Whom will you vote next time?
  18. Is democracy in favor of current political situation?
  19. What is the role of youth in current political system?
  20. What are your views on the current political system?

Deep Questions to ask Friends to Learn of Relationships Matters

The following are the major questions through which you can know about the feelings of the relationship of your friends and loved ones.

  1. Is premarital sex good or not in your views?
  2. What are the attributes that you are looking for in spouse?
  3. What are your spiritual and religious beliefs and do you stand by your beliefs?
  4. Is saving money important for you or not?
  5. How important is to invest money in a specific area?
  6. How is important is sex in your life?
  7. How important is sex in a marriage in your views?
  8. Are you in to managing the long distance relationships or you will never go for it?
  9. What are the things which can destroy relationships as per your views?
  10. What are the unforgiven able things in a relationship?
  11. Do you like kids?
  12. Do you have a desire to have kids and is it important for you to spend time with your spouse or family?
  13. Who is more important for you either parents or spouse and why?
  14. Where do you like to spend time with your family?
  15. What are the basic elements which lead a relationship to success?
  16. Do you think that one can remain friends with their exes?
  17. Is emotional cheating a good or bad thing and why?
  18. Do you have a belief in open relationships?
  19. Have you ever cheated on your boyfriend/ girlfriend?
  20. Have you ever had crush on your high school teacher?

Deep Questions to ask your Girlfriend/ Boyfriend

The following are some question that you can ask to your girlfriend / boyfriend and enjoy knowing about their personal matters.

  1. How long before you had realized that you wanted to be friends with me?
  2. Are you currently looking to be in commitment with someone else?
  3. What was my first impression on you?
  4. Which of my attribute admired you to be friends of me?
  5. Will you buy me a costly gift to surprise me or would you first consult me for spending money?
  6. Would you like to go to bed and have rest or go to kitchen for helping your mother?
  7. Would you like to cook for me or order from a restaurant when you invite me at your place for dinner?
  8. What do you think is best either a working mother or a mother who take care of you and stay at home?
  9. What do you prefer either having an impact over the entire world or having a good impact on your friends and family members?
  10. Which song is best suited in case of your relationship with your girlfriend?
  11. Which couple either real life, fictional, or of movies is reminding you the best moments related to your past?
  12. What do you think of proposal either being a private affair or should be disclosed in public?
  13. If you ever have children then what features of yourself would you like to have in them?
  14. If you ever have children then what features of me would you like to have in them?
  15. What are the top things that you are appreciating about me?
  16. What three things do you think you and me are having in common?
  17. What are the three biggest differences among us?
  18. What facial features do you think we are having in common?
  19. Is there anything that you are thinking we may have in common when it comes to our relationship of friendship?
  20. What are the things on which you would never compromise throughout your life even with me?

Deep Questions to Ask Boyfriend and Girlfriend regarding Spiritual and Serious Beliefs

The following are some major questions that you must ask your boyfriends / girlfriends which are related to the spiritual and serious beliefs.

  1. Do you have any belief in life after death?
  2. Do you have a belief in heaven and hell?
  3. Do you have any belief in having soulmates?
  4. Do you have a belief to forgive and forget or you remember and plan to take revenge?
  5. When you have kids, what will be your biggest hope and fear for them?
  6. What is the area or part of your life where you feel like something important is missing?
  7. Do you have a belief in do good and have well?
  8. Do you have a belief that there is a virtuous person in each of us?
  9. Do you think your significant other can be both your best friend and your lover?
  10. Is your current life the way you have been thinking throughout your childhood?
  11. Do you think it’s better to have the worst house in a nice neighborhood or the best house in a bad neighborhood?
  12. Do you like to have a life full of money and luxury or a life without money but love everywhere?
  13. Do you have a belief that sex before marriage is a sin?
  14. Do you have any belief that incent may be allowed?
  15. Do you think that a positive aspect towards something can make the life better?
  16. What do you think that children are burden or blessings of God?
  17. Do you believe in the fact that opposite sex are always attractive for each other?
  18. Do you mind having a relationship with a bisexual person?
  19. Do you have anyone in life for whom you can risk your life?
  20. If I was giving birth to our child and complications arose that meant only one of us would make it, who would you save?
  21. What you will say to people after I die?
  22. How will you remember me as a person after I die?
  23. If you have a time machine and could go back in past, what will be the strangest advice you give to yourself?
  24. If you have a time machine and could go back in past, what will be the best advice you give to yourself?
  25. What is story of your life?
  26. Do you have any wish to act in a play and play the character you have been dreaming of?
  27. Who has been the most affectionate person in your life?
  28. Can you complete the sentence that “I wish to have someone with whom I can…”?
  29. Do you have any secrets from you me or your partner?
  30. If you die tonight, will you have any regrets about not telling something important that we must know?
  31. What is bitter truth of your life?
  32. What are the problems that you are having in your life as of now?
  33. Define the biggest struggle of your life that you have faced till date?
  34. Will you be requiring my help in your hard times?
  35. Have you ever beaten by a group of people?

Deep Questions to Ask your Friends

  1. Do you have any morals for which you would stand till your last breath?
  2. Do you have any goals which are not achieved yet?
  3. Do you like darkness or light?
  4. Do you go for outing alone or you like to go out with your friends in form of groups?
  5. What is the most attractive part for you in the opposite sex?
  6. Do you like to lick or getting licked?
  7. What is your favorite book?
  8. Have you ever tried to understand your holy book?
  9. Do you have anything to tell me before you die?
  10. What are the things that you hate about me?
  11. Do you want to die a virgin?
  12. Are you still a virgin?
  13. How many times you have been in love till date?
  14. Do you believe in love at first sight?
  15. Do you think love happens only once in life?
  16. Have you ever longed a woman who is double of your age?
  17. Do you ever slept with your maid?
  18. How many times you masturbate in a day?
  19. What was the worst date of your life?
  20. Which is the best moments of your life?
  21. What is the breaking deal for you in a relationship?
  22. Do you have religious beliefs or you a secular?
  23. Do you think all religions are true?
  24. What strange habits you have in life?
  25. Do you often see wet dreams?
  26. Do you want financially stable partner?
  27. Are you financially stable yourself?
  28. Have you ever lost someone with whom you were too close?
  29. Have you ever seen your parents naked?
  30. What is your ideal weekend destination?
  31. Do you prefer having tea or coffee?
  32. Do you like to have best friends in same sex or opposite sex?
  33. Do you prefer a relationship or one night stands?
  34. To which parent are you closer and what is its reason?
  35. Do you have bad phases in your life?
  36. What are the evergreen phases of your life?
  37. Are you currently having your dream job or you has dreams of something else?
  38. What is making you feel accomplished when you think behind?
  39. Do you have any regrets in life when it comes to one night stands?
  40. Have you ever been involved in group sex?
  41. Have you been sleeping with your best friend?
  42. Are you bisexual?
  43. What has happened to you which you think is the most embarrassing thing happened to you in life?
  44. Do you tell lies?
  45. What is the biggest lie that you ever told to someone?
  46. Do you cheat in exams?
  47. Have you ever been caught red handed in exams while cheating?
  48. Would you give up a poker night with the boys to take care of your sick girlfriend?
  49. Do you believe in open relationships?
  50. Do you think you can share your partner with your best friend?
  51. What will you think if your girlfriend ever want you back in life?
  52. What is your favorite movie of all time?
  53. How many people have cheated on you?
  54. With how many people you have cheated?
  55. Do you believe in as you sow so shall you reap?
  56. Do you have any phobias?
  57. What makes you angry most of the times?
  58. Have you ever beaten your partner?
  59. Are you comfortable with sharing your password with your friends and family members?
  60. Do you like to live alone in small apartment or you want to have a large family?
  61. What you do when you get horny?
  62. What is the darkest secret of your life?
  63. Will you tell me wrong answers for the questions that I ask you now?
  64. Have you ever wanted to be man/ woman?
  65. Which questions will you refuse to answer me?
  66. What does love mean to you?
  67. Do you think love ends in having sex?
  68. Do you think that you will be a good parent?
  69. Who is the best friend you have in life?
  70. Whom are you scared to lose?
  71. Are you thankful for any person in your life?
  72. Who has been admiring you the most?
  73. What importance do I have in your life?
  74. Do you think a person may be given a second chance if she/ he is not done well in first?
  75. What have you learnt from your past relationships?

Bonus Deep Questions to ask your Friends

The following are some bonus deep questions to ask your friends which may help you to know them well.

  1. Do you believe in New Year resolutions?
  2. When have you felt your biggest adrenaline rush?
  3. Do you have plans to move to other city if your partner ask you for moving?
  4. Do you have enemies in life?
  5. Have you ever tried to kill somebody?
  6. If you get a chance to kill someone, who would he / she be and why?
  7. Have you ever been raped?
  8. If you get a chance to kiss a showbiz star, who he / she would be?
  9. Do you want to become an actor?
  10. Do you sing?
  11. Are you a bathroom singer?
  12. How much will you rate me on a scale of 1 to 10?
  13. Do you consider me a biased person?
  14. Do you have any tattoos?
  15. Would you like to have a tattoo on your genitals?
  16. Do you like dirty sex?
  17. Have you ever had bad sex?
  18. Do you have any fantasies in mind which you want to happen to you in real life?
  19. Do you believe that dinosaur ever exited?
  20. Would you like to have a selfie with snake or your friend?
  21. What turns you on?
  22. Do you watch porn?
  23. With how many persons you have been with in bed so far?
  24. What is the biggest nightmare of your life?
  25. How many times you had one night stands?
  26. Have you ever done sexting?
  27. What attract you the most in women / men?
  28. Who is your favorite sibling and why?
  29. Who is your favorite actor?
  30. Would you like to act in a B grade movie?
  31. Would you like to be a hero/ heroine of porn movie?
  32. Have you ever wanted to sleep with a porn star?
  33. How long you last in bed?
  34. Do you talk dirty on phone or in real life?
  35. Do you like double meaning talks?
  36. Would you like to get married to your maid?
  37. What experiences in your life has made you the person you are today?
  38. What is the wish which you are still waiting for to be accepted by God?
  39. Do you have faith in oneness of God?
  40. What according to you is a perfect life, and how you would you try to make it for yourself and me?
  41. What is the strangest wish that happened to you in real life?
  42. Do you think dreams come true?
  43. Which kind of dreams do you often see?
  44. Have you ever seen God in dreams?
  45. Do you think all religious books are true?