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525 Deep Questions to Ask – A Complete List

525 Deep Questions to Ask – A Complete List

Updated on November 22, 2021 | Published on July 24, 2021
Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling), Life & Relationship Coach
525 Deep Questions to Ask – A complete list

Have you ever tried to connect with someone at a deeper level and struggled with how to get along with a good conversation? Did you ever get stuck in a monotonous discussion where you didn’t know what to talk about? We all have faced such a situation many times in our daily lives. Right?

When you wish to know someone well and make the conversation insightful and free-flowing, you need open-ended deep questions to ask them so as to take the discussion to a next level of meaningful connection.

These questions stimulate your thoughts and help you know someone, beyond the surface. Read on to know more about such rooted and digging queries that can make a discourse go on for hours.

Deep questions to ask – meaning

SUMMARY
Deep questions to ask are casual, formal, and open-ended inquiries that you may ask others to know and cross-examine the person in detail. It also reduces monotony and boredom and keeps the chat interesting for a long time.

Our busy schedule and everyday chaos do not allow us to connect with others at a deeper level. 

Most of the connections are superficial encounters that don’t allow us to know each other well.

Sometimes we struggle to find the right question to keep up with the flow of our talk. Many of the questions that you are using in your chats are only generic. 

In such a situation, deep questions can be asked that are insightful, have a purpose and meaning to serve. 

It can help you know the person’s true nature, values, and priorities in life. These deep questions can be related to their personal, professional, or social life. 

You can easily get an idea about various aspects of their life, beyond the basic information that may not excite you at all.


Deep questions to ask a girl

Sometimes you may struggle to continue a conversation for a long time with a girl whom you have first met, simply because you were confused about what to ask and how to know her in a detailed manner. 

An icebreaker to this would be to ask a few general questions in the beginning and then quickly switch over to deeper questions that may help to roll the ball towards insightful, thought-provoking, and great conversations

  1. Can you remember any single event of your life that has shaped you the way you are today?
  2. What are your deepest secrets that you have always preferred to keep under cover? Would you like to share it with me?
  3. What is the difference between morality and ethics?
  4. Do you think your present life situation is better than what it was five years ago? Why?
  5. Is there anything that can keep you awake at night?
  6. Do you believe in self-improvement? Have you ever tried doing it? How?
  7. How do you maintain your inner peace?
  8. What is that one thing that makes you angry instantly and why?
  9. What is your greatest accomplishment till date?
  10. Is there anything that you think you should have learned long back? Why?
  11. Do you believe in the existence of God?
  12. Do you harbor resentment or allow it to let go? How and why?
  13. Do you think that failures can teach you much more than success? Why?
  14. What do you do on a Friday night?
  15. What is the best gift that your mother gave you? 
  16. How do you spice up your free time?
  17. Whom do you look up to in times of sorrows and sufferings? Why?
  18. Can you imagine your life without a mobile phone?
  19. Which one is your best holiday destination till date?
  20. Do you live with regrets? Why?
  21. What are your character flaws? Have you ever tried changing them?
  22. Do you think it is hard to forgive others who sin against you? Have you ever tried doing it?
  23. How do you handle criticisms?
  24. What is your best way to resolve family issues?
  25. What personal boundaries have you set around yourself and why?

Deep questions to ask a guy

Sometimes you may shy away from asking deeper questions to a guy whom you like. 

As such the connection may become superficial with much unsaid stuff between the two of you. 

Maybe you need some really good stuff to talk about and know each other’s preferences and life choices. 

You can check out these personal and philosophical questions to get better insight into his nature and personality.

  1. What is that one thing that can make you cry?
  2. Are you a man of hard work or destiny? Why do you think so?
  3. What are your views about the afterlife?
  4. Do you believe in the existence of aliens?
  5. How would you define love?
  6. Describe your perfect day.
  7. What is that one thing that can annoy you quickly? Why?
  8. Do you have deepest fears? What is it?
  9. Are you happy with your present job?
  10. How would you prefer to end a long and hectic day?
  11. What is that one thing that you will never allow your partner to do?
  12. Are you a forgiving person?
  13. What are your strengths and weaknesses?
  14. Describe your moments of true happiness?
  15. Do you have bad habits? Have you ever tried to change them?
  16. Can you remember the happiest moments of your childhood?
  17. When do you feel really low? How do you cope with it?
  18. What are you most grateful for in your life?
  19. Who influenced you the most in your life? Your mom or dad.
  20. What are the things on your bucket list this year?
  21. How do you prefer to spend your weekends?
  22. Are you a family man?
  23. Describe one incident of your life that made you laugh the most?
  24. Have you ever tried driving a sports car?
  25. Who is your favorite sportsperson?

Deep questions to ask friends

Friendships are an integral part of your life. They are the ones who will be with you thick and thin. 

There are some friends who are your best pals and greatest critiques. 

While there are a few with whom you are still trying to build up an intimate connection. 

You wish to know more about them, their life, and ideologies in general.

You should ask them some deeper questions to keep the conversation going on in detail so that you people can get along well for years.

  1. Are you unstoppable if you really feel that you need to do something?
  2. What friendship qualities do you have in you that can make you a good friend?
  3. Do you think you have something that you have never said aloud?
  4. What makes you feel most happy?
  5. Is there anything that scares you the most?
  6. Has your best friend impacted you in any way?
  7. Where do you see yourself five years from now?
  8. Describe your favorite childhood game.
  9. What are your thoughts on spirituality?
  10. Do you think that God exists somewhere? 
  11. Do you like clarity or ambiguity?
  12. If you are given a chance to become the mayor of your town for a day, what things would you like to change and why?
  13. Which is bigger – Love or hatred?
  14. Which is stronger – revenge or kindness?
  15. Do you think discipline is important for a successful living? Why and how?
  16. What are your ideas on marriage and family life?
  17. Do you believe in the concept of co-parenting? Will you follow it when you become a parent?
  18. Which is your favorite cuisine?
  19. What your perfect date will look like?
  20. If you could eat and sleep the way you wanted, what would you eat and how long would you sleep?
  21. Who is your partner in crime whenever things go wrong?
  22. If a genie comes and grants you three wishes, what would they be and why?
  23. Have you ever dealt with a complex situation differently than others? Did you succeed in it?
  24. Who comforts you when you are sad or in a bad mood?
  25. What is the most embarrassing moment of your life that you would never like to share?

Deep questions to ask your best friend

Your best friend is someone you are too connected with. They are the ones with whom you can share your happiness, sadness, deepest secrets, and worries. Thus, you would prefer to know everything about that person. 

A conversation can become monotonous and boring if you do not have enough deep topics to talk about. You would look for a list of interesting questions to ask a your friend

  1. Who do you follow – head or heart?
  2. How do your friends describe you?
  3. What are your long term life goals that you are striving to accomplish?
  4. If you could change anything about your present life, what would it be and why?
  5. Who inspires you the most in your life?
  6. What do you do when you’re grumpy?
  7. Have you ever confessed your mistakes? To whom and why?
  8. Can you remember the last time your mother fed you with her own hands?
  9. What’s your favorite tourist spot and why?
  10. How do you start your mornings?
  11. What is the last thing that you do at night before going to bed?
  12. Have you ever experienced a moon bath in your life? If yes, describe your feelings.
  13. Have you ever tried paragliding?
  14. Do you believe in reincarnation?
  15. Are you your greatest critic? Why?
  16. How would you like to pamper yourself, if given a chance?
  17. Can you describe your deepest wishes and unfulfilled desires?
  18. When was the last time you celebrated your birthday?
  19. Do you enjoy discussions on sex and physical love?
  20. What offends you the most?
  21. Do you have siblings? How do they influence your life and living?
  22. Have you ever been a victim of office politics? If yes, how did you deal with it?
  23. Are you easy-going or difficult to deal with?
  24. What are your worst worries that can even give you sleepless nights?
  25. Have you said a difficult goodbye to someone? When?

Deep questions to ask your boyfriend

Whenever you are chatting with your boyfriend, you will always try to ask deep questions that help you to know him well. You might be interested to know the kind of person he is, his likes and dislikes and whether he would be a perfect man for you.

  1. What is your guilt-free pleasure?
  2. How many relationships have you had till now?
  3. Who is your first crush?
  4. What qualities are you looking for in your wife?
  5. What can give you an instant smile?
  6. How many times would you prefer to have sex in a week?
  7. What is your best sexual experience or erotic fantasy?
  8. Which one is your preferred sex position?
  9. Do you exercise regularly?
  10. Which is your favorite indoor game?
  11. Can you talk over the phone for hours?
  12. Do you like to collect anything? If yes, what is it?
  13. Has anyone ever played freaky pranks upon you? What was your reaction?
  14. Do you harbor any jealousy against anyone? Why?
  15. Has anyone ever cheated you? What did you do?
  16. What is your life’s philosophy?
  17. Describe the feel of your first kiss
  18. Have you ever tried cooking a yum dish for your ex-girlfriend? Will you do it for me as well?
  19. How do you define a healthy love relationship?
  20. Do you still remember your pre-school teachers?
  21. Do you procrastinate? How often and why?
  22. From whom do you seek a piece of advice when things go wrong?
  23. What are your core values and beliefs that guide your life?
  24. What is your opinion about infidelity?
  25. Are you an early bird or a night owl?

Deep questions to ask your girlfriend

Are you tired of talking about similar issues with your girlfriend? And you want something more to get into an in-depth conversation. Then this list of good questions is meant for you.

  1. How do you measure success in relationships?
  2. Do you embrace your moments of solitude?
  3. How many men have approached you till now?
  4. What is the one thing that you miss about your ex? And why?
  5. Can you imagine your life without a mobile even for a day?
  6. What makes you feel good about our relationship?
  7. Is there anyone who broke your trust and made you suffer a lot?
  8. What are your views about a perfect marriage?
  9. Do you like children? What are your thoughts on parenthood?
  10. Tell me something about your parents that you have never shared with anyone?
  11. Have you ever been misunderstood in a relationship?
  12. What are the most important things that you look for in a relationship?
  13. Describe your bad failures that still haunt you?
  14. Who do you look up to as a role model?
  15. Are you still connected with your high school friends?
  16. Do you consider your job good enough?
  17. What can I do to make your day a little better?
  18. Is there anything that can make you nervous quickly?
  19. What are your thoughts on the importance of privacy in relationships?
  20. Name three things you are most grateful for in your life?
  21. How important is having children after marriage?
  22. Have you ever planned for your retirement?
  23. What are your ideas on long distance relationships?
  24. If you could change one thing about me, what would it be and why?
  25. How do you want others to remember you after death?

Deep questions to ask someone

Sometimes you would love to know about someone in detail. Few simple getting-to-know questions don’t work at all. As such, deep questioning can do wonders. This list of questions can do the needful:

  1. What is the best compliment that you have received and from whom?
  2. Who is your favorite story teller?
  3. Are you a cleanliness freak?
  4. What are your views about ecological balance?
  5. Do you think human beings are responsible for the extinction of many animals?
  6. How comfortable are you speaking in front of a large audience?
  7. Do you like surprises? Why or why not?
  8. Has anyone ever told you that you are the best person they have ever met?
  9. Do you think there is something in you that you would like to change?
  10. Are you an introvert, ambivert, or an extrovert?
  11. Tell me something about the worst phase of your life? How did you overcome the problem
  12. Do you think you are patient enough to deal with trying times?
  13. Who is your favorite cricketer and why?
  14. Have you ever suffered a broken relationship?
  15. Have you ever written a gratitude journal?
  16. What are your thoughts on sibling rivalry?
  17. What can you do to help the poor people?
  18. Can you list your top f bad habits? Have you ever tried to undo them?
  19. Who is your favorite spiritual guru and why?
  20. If you are given a challenge to spend 24 hours on a bed without putting your feet down, will you agree to do it? Why?
  21. What was the last movie you have seen?
  22. What is unconditional love? Your views on it
  23. Describe your first dinner date?
  24. Do you have pet peeves that may annoy others?
  25. Can best friends become great life partners? How far do you agree with it?

Deep questions to ask your crush

Are you eager to know whether they like you as much as you do? These deep questions will help you know their feelings towards you and also give them an idea of how you feel about them. 

Building up healthy connections with your crush goes a long way towards long-term romantic relationships.

  1. If I call you really late at night or very early in the morning, will you pick up my call?
  2. What are your future goals that you would love to accomplish with me by your side?
  3. If I tell you to sing a song for me now, what song will it be?
  4. What will be a perfect vacation with your crush that you would prefer to cherish forever? 
  5. Will you help me realize my goals and aspirations?
  6. What made you think that I am the right person for you?
  7. Have you tried to rectify your bad habits?
  8. What is a nice thing that you have done for someone?
  9. Can you binge watch TV series for hours?
  10. What makes you a good partner?
  11. Can you control everything happening around you? Or do you feel that it’s only a matter of good or bad luck?
  12. When you watch television, what channel do you quickly skip to and why?
  13. Are you a people pleaser or feel not bothered about what others think about you?
  14. Is there any rule that defines your life? What is it?
  15. What are your views about death? 
  16. Do you think that you are living a fulfilled life?
  17. What are your views on true beauty?
  18. Do you think priorities in life change with time and age?
  19. Have you ever set a daily routine for yourself and struggled to follow it?
  20. Do you have a sweet tooth?
  21. Do you like tattoos? 
  22. How do you handle your sad days?
  23. Are you scared of any specific animal species?
  24. What is one stupid thing you did and never told it o anyone? Can you share it with me today?
  25. Do you believe in love at first sight? Did you ever fall in love in such a way?

Deep questions to ask people

This list of questions is meant for anyone whom you wish to know a little more than usual and would love to engage in deep conversations.

  1. Do you think money can buy you happiness and inner peace?
  2. What makes you different from your team mates?
  3. Do you think you can make a difference in someone’s sad and gloomy life?
  4. Are you resilient enough to fight adversities?
  5. How do you spend your leisure time?
  6. Have you got any new found hobbies?
  7. Who takes care of you when you are not well?
  8. What are your views on the importance of education?
  9. How is your connection with your parent-in-laws?
  10. How often do you have outside food? Are you a foodie?
  11. What motivates you to work hard and achieve your precious goals?
  12. Do you accept mistakes?
  13. Are you facing any challenge right now with regard to your career?
  14. “Pen is mightier than a sword”- Can you give your views on this quote? 
  15. Do you believe in soulmate relationships? Do they really exist?
  16. Have you compared yourself with someone? Why?
  17. Are you aware of your character flaws?
  18. Are you holding on to resentments that you need to let go of?
  19. When you will be 60 years old, will your life be the same as it is now?
  20. Have you ever experienced failure without trying? Was it worth it?
  21. How well do you relate with your colleagues?
  22. Do you discuss your private life and personal issues with colleagues and teammates?
  23. What has life taught you hard?
  24. Are you a perfectionist?
  25. What will you say to your inner child? 

Deep questions to ask your partner

Getting to know your partner is not an easy job. Right? You can keep a perfect blend of fun questions along with deeper stuff to dig into them in detail.

  1. What small act of kindness have you done recently?
  2. What is your precious possession?
  3. Name 10 personal values that guide your life?
  4. What are your views about arranged marriage? Does it work?
  5. Are you hopeful of having a better tomorrow for yourself and family?
  6. Who comes to your mind when you think of selfless love?
  7. Have you ever broken traffic rules? When and why?
  8. Who is your celebrity crush whom you adore?
  9. Do you think that life should be governed by ethics?
  10. Did you feel guilty for a mistake that had hurt someone else?
  11. Have you ever tried water sports?
  12. How would you define beauty?
  13. Which is your favorite emoji?
  14. What is the big life lesson that you have learned from your mom and dad?
  15. What makes you fearful? Why?
  16. Will you allow your partner to follow her dreams? What dreams have you seen together?
  17. What one thing can I do to cheer you up?
  18. What’s your idea of a perfect family life?
  19. Can you remember your high school days?
  20. Are you a compulsive buyer?
  21. Do you have any future business plans?
  22. Have you ever cheated anyone? Why and how?
  23. How skilled are you in managing time?
  24. When do you feel really agile and active and can work for long hours?
  25. Do you have some questions for yourself?

Deep questions to ask yourself

Sometimes in order to know the in-depth corners of your own ‘psyche’, you should ask deep questions to yourself. 

  1. When was the last time I said ‘sorry’ to someone?
  2. What project am I working on right now?
  3. Am I comparing myself with any celebrity?
  4. When was the last time I called my best friend?
  5. With whom do I share my sorrows?
  6. Do I think weak people cry more than strong people?
  7. What have I learned in a hard way?
  8. Do others judge me the way I don’t like?
  9. Should I celebrate my moments of joy? How often?
  10. Why can’t I give my favorite things to others? What stops me from doing that?
  11. Do I believe in living or existing?
  12. Should I try to live my life differently?
  13. What adds value to your life?
  14. Do you know how to let go of past hurts and move on with your life?
  15. Are you safe enough from within?
  16. Are you an emotional person?
  17. Do you express your feelings explicitly?
  18. Are you comfortable being alone?
  19. Am I grateful towards those who have done something good to me?
  20. Should I make others realize that I need some ‘me time’ now?
  21. Am I in love with my work?
  22. What risks can I take to improve my life?
  23. How well do I connect with others?
  24. Am I a good friend?
  25. Can I do something to improve my relationships with others who love and care for me?

Deep flirty questions to ask a girl

Women always love to be attended to and cared for. They want men who fall for them. If you have some flirty questions ready on your first date, then you have a better chance to win her heart. She will consider you a man of intelligence, wit, and humor. You will surely stand out more than other fellow dudes in the town.

  1. What is a perfect kiss?
  2. What can you do with your partner to add spice and fun in the relationship?
  3. Would you mind holding my hand for a minute?
  4. What is deep love making? Your views please
  5. Has anyone told you that you’re looking quite sexy today?
  6. What is your comfortable nightwear?
  7. Describe your worst date?
  8. Do you enjoy funny moments with your partner?
  9. Did you ever have a crush on a professor?
  10. What is that silly thing that your partner did with you? Did you like it?
  11. How will you react to your partner’s criticisms?
  12. Will you allow your partner to hug you on a first date?
  13. Describe your best dine out with your partner?
  14. Are you comfortable to try out new things in sex and intimacy?
  15. What’s your choice – bad boys or good fella?
  16. What defines a perfect guy?
  17. Would you like him to give you a sexy look when you dress up well?
  18. Are you a party girl?
  19. Would you get jealous if you see your man flirting with someone else?
  20. Do you keep secrets?
  21. Are you good at keeping promises?
  22. What weird things do you often do with your partner?
  23. Are you possessive of the person you love?
  24. Which behavior of his can make you go mad instantly/
  25. Has he ever tickled you?

Deep personal questions to ask a guy

If you do not have enough interesting questions to ask a guy, the conversation may become really awkward and boring. It might lose its spark and the communication will be superficial and dull. You can keep some deep questions in hand to avoid such unexciting moments coming up in the communication process.

  1. How does your bedroom look? Is it tidy or a mess?
  2. Do you believe in the statement that ‘perfection is a myth’?
  3. Are you a mama’s boy?
  4.  Who gave you pocket money when you were a young boy?
  5. How many girlfriends do you have?
  6. Who is the most special person in your life without whom you cannot imagine your everyday living?
  7. Do you think that life will always give you a second chance?
  8. What small changes can you make in your everyday living to make it more interesting and exciting?
  9. Are you a nature lover?
  10. Have you ever ridiculed someone wrongly?
  11. Is there anyone in your life with whom you can just talk to about anything without hesitation?
  12. Do you have empathy? If so, how?
  13. How will you handle your enemy?
  14. What makes you lose your self-confidence?
  15. Have you ever tried to please someone without a reason?
  16. How do you set your priorities in life?
  17. Have you ever lived through your failures? What was it like?
  18. Do you believe in creating your own reality by the power of your thoughts and beliefs?
  19. What is your opinion on the saying ‘Honesty is the best policy’? 
  20. What is your moral code of conduct when you attend formal parties?
  21. Do you think that sometimes your limitations and imperfections can help you win big deals?
  22. Are you a leader or a follower? Explain your views?
  23. Have you ever volunteered in a community welfare program?
  24. What compliments do others give you quite often?
  25. How do you handle a fight with your boss?

Deep questions to ask to get to know someone

Some good conversation topics include questions that are meaningful and quickly enhance your know-how about others. How will you enhance your self-love quotient?

  1. Do you think you should cultivate empathy to become a better version of yourself?
  2. What is your opinion on grief and healing?
  3. How often do you get hooked on social media feeds in a day?
  4. Have you ever suffered a FOMO crisis? How did you deal with it?
  5. Do you hesitate to take steps towards your overall well-being?
  6. What would your perfect Sunday look like?
  7. What is your favorite topic to talk about?
  8. Which one will you choose with your girlfriend – being nice or naughty?
  9. What’s the right age to have sex?
  10. How do you respect a person’s privacy?
  11. Do you have a life changing moment that shaped what you are today?
  12. How do you deal with people who are jealous of you?
  13. What’s your opinion on the saying ‘A friend in need is a friend indeed’?
  14. Are you a movie buff?
  15. What music soothes you when you are stressed out?
  16. How do you feel when you meet new people? Do you get scared or feel excited?
  17. Are you courageous enough to fight adversities?
  18. What subjects were you good at when you were in high school?
  19. Do you miss your college fun days and hangouts with your best pals?
  20. Do you feel that your life was much less stressful before than what it is now?
  21. How do you handle distractions when you work in a space with too many people around you?
  22. Describe your favorite place in this world that can give you absolute happiness and bliss?
  23. Do you still feel guilty for any wrong decision that you might have taken in the past?
  24. What makes you a humble being?

Deep questions to ask about life

When you ask deep questions about life as conversation starters, it helps you to connect with someone at an emotional and spiritual level.

  1. What is your life’s philosophy?
  2. Do you think you need to connect with yourself at a spiritual level to know the hidden secrets lay there?
  3. How are you as a human being?
  4. Are you a religious or spiritual being?
  5. How have you felt your biggest adrenaline gush that you would never forget?
  6. How many funny questions can you ask someone in one minute?
  7. Should we live our life seriously or casually?
  8. What qualities of your partner can get them closer to you?
  9. Describe the turning point in your life?
  10. What can bring you closer to your goals?
  11. How do you relate yourself with online dating?
  12. What random questions come to your mind quite often?
  13. Do you have any biggest fears about life in general?
  14. What is the craziest thing you’ve done recently that gave you a lot of fun?
  15. Do you think sharing your passwords even with family members is not worthy? Why?
  16. Can you spend the rest of your life on a deserted island?
  17. How many languages can you speak fluently?
  18. How will you undo the biggest regret in your life? Can you really do it?
  19. Have you ever realized the power of prayer?
  20. How hot do you think the sun is?
  21. Can you live your life according to a fixed plan?
  22. Are you saving enough money to secure the future of your family?
  23. How can you motivate others to follow a nutritious diet and healthy lifestyle?
  24. What are your views about the laws of the Universe?
  25. If you are given a day to spend in a 5 star resort anywhere in the world, which one would it be and where?

Deep questions to ask about love

The chaos of everyday life keeps you away from having an in-depth conversation with your special someone. Whenever you meet people, you may be confused about what to ask, how to maintain a good conversation, and go on for some time. 

Few deep questions that may keep alive the relationship are:

  1. How did you feel when you had your first kiss?
  2. When was the last time you said ‘I love you’?
  3. Where would you wish to go for your honeymoon?
  4. Do you enjoy the closeness that you people share?
  5. Is trust important in maintaining a healthy relationship?
  6. Who is the one who speaks more in the relationship? Is it you or your partner and why?
  7. For you, was it love at first sight?
  8. Do you think marriages are made in heaven?
  9. What are your future plans with your partner?
  10. What is the first gift that your partner gave you?
  11. Do you love yourself?
  12. How much love can you share with your partner? Is it measurable?
  13. Is there any difference between a man’s love and a woman’s love?
  14. Do you give space in your relationship?
  15. Is there anything called ‘ideal love’?
  16. Why do couples fight with each other?
  17. Do you think too much love should be avoided?
  18. How can you build a lifelong relationship?
  19. Do you think love is eternal?
  20. Why do people say ‘love is blind’?
  21. Do you think that love can fade away with time?
  22. Can love replace the hatred surrounding humanity?
  23. What was your experience of a love bite?
  24. Should we set healthy boundaries in love and relationships? Why?
  25. What is your most common relationship deal breaker?

Deep questions to ask in a relationship

Relationships bloom and evolve when two people know each other well and that’s only possible if you ask deeper questions that can connect you at a core level of love and comfort. These questions are great at doing this:

  1. What do you look for in an intimate bonding?
  2. Do you think partners should be honest with each other?
  3. How would you prefer to maintain integrity in the relationship?
  4. Do you think that partner’s should maintain each other’s privacy?
  5. Have you ever checked your partner’s phone?
  6. Can your love mate be your best friend?
  7. How do you handle conflicts and disagreements with your partner?
  8. How much time do you people spend over a phone in a day?
  9. Do you think that your parents can also be your best friend?
  10. What kind of relationship do you have with your colleagues?
  11. Do you fight with your best friend?
  12. Who takes the last call in an important decision? You or your mom?
  13. Are you the one who sulks a lot after a big fight with your friend?
  14. How do you spend time with your father?
  15. Are you still in touch with your school friends?
  16. When was the last time you met an old friend just by chance?
  17. Does your partner help you to overcome stress?
  18. Do you prefer getting connected and spending quality time at a family function?
  19. Can dishonest acts ruin relationships forever?
  20. Are you jealous and insecure about your partner? Why?
  21. Is your partner resentful at times? How can you help him/her?
  22. Can you do mind reading and say that your partner is going through some emotional problem?
  23. How difficult is it to handle a breakup that you have never wanted?
  24. Can relationships have a second chance after you and your partner moved apart from each other? Is it possible?
  25. How do you deal with ungrateful people?

Deep questions to ask kids

Sometimes you need to connect with children at a deeper level just to know what’s going on in their small little world. 

  1. What do you love doing in your free time?
  2. Who takes care of your studies at home?
  3. How well are your connections with your cousins?
  4. Can you describe yourself by using five words?
  5. Which is your favorite subject and why?
  6. What do you want to become when you grow up?
  7. When was the last time you were kind towards someone?
  8. Do you share your personal belongings with your friends?
  9. Who loves you more at home?
  10. How often do you visit your grandparents?
  11. How much time do you spend in outdoor games and activities?
  12. Which is your favorite indoor game?
  13. What makes you the way you are?
  14. Are you scared of darkness?
  15. Do you follow a time table while you’re preparing for examinations?
  16. Who helps you get ready for school?
  17. How do you celebrate your birthdays?
  18. Do you help your parents in household chores?
  19. Who appreciates you more at home?
  20. Who is your favorite fictional character that has influenced your life greatly?
  21. Which superhero has influenced your life and living significantly?
  22. How do you resolve your fights with your sibling?
  23. Who helps you overcome your failures and how?
  24. Have you ever visited an orphanage? How did you feel about it?
  25. What makes you sad in no time?

Deep questions to ask teachers

If you want to know more about a teacher’s life and their work in general, these deep questions can help to get into the details of everything that you wish to understand and know about.

  1. How can you use technology in learning?
  2. What are your views about online learning?
  3. Is it possible to connect emotionally with each and every child in your class?
  4. How do you make your lessons interesting?
  5. Do you shout at kids while you teach in a regular classroom setup?
  6. How will you handle an inattentive child?
  7. What is your disciplinary style?
  8. How can you use the principles of child psychology to motivate your students to learn more?
  9. Do you think that children should learn things at their own pace?
  10. What are your views on individual learning in education?
  11. How good are you at your work?
  12. How can comparison affect children?
  13. Are you a kind teacher?
  14. What is one gift that you have received from your students?
  15. How will you handle a cranky kid in a classroom setup?
  16. Are you patient enough with small kids?
  17. When do you lose your temper?
  18. Can you manage and comfort crying kids?
  19. Why have you taken up teaching as a profession?
  20. What are your views on classroom management?
  21. How is your relationship with your co-teachers?
  22. How long do you take to correct the notebooks of your students?
  23. What is your success story as a teacher?
  24. Can you remember the worst lesson that the teaching profession has taught you?
  25. What makes you feel the most satisfied?
  26. Have you ever shared lunch with your students?

Deep questions to ask about values

Your values actually determine the kind of person you are. Values are important for a definite purpose and make you the way you are. Few deep questions to ask someone about values could be:

  1. Can values help you attain success?
  2. What is immorality? Share your views
  3. Who taught you the basic values of life?
  4. What can you do to keep your values intact?
  5. Can human values bring positive change in this world? How?
  6. Describe your five principle values and what they mean to you?
  7. Do you think life can become unruly without values?
  8. Can values help to set life’s purpose?
  9. Would you like to use the values in building your self-image?
  10. Have you ever visited a spiritual teacher to learn life’s greatest values?
  11. How does family impact the type of values you possess?
  12. Would you love to be remembered as an ethical person after you are no more?
  13. How can you use values to accomplish career goals?
  14. What values make you different from others?
  15. How will you judge whether something is right or wrong?
  16. Are you a helpful being?
  17. Do you think selflessness can add value to your life?
  18. What are you ashamed of?
  19. Have you ever had regrets of not helping someone in need?
  20. Should we compare our life with someone else’s? Why or why not?
  21. How can a positive mindset change your life’s perspectives?
  22. Does your value system match with your partner?
  23. What values have you nurtured in your child?
  24. Do you think that success and failures are the two sides of the same coin?

Deep questions to ask about Life goals and motivation

Sometimes you may want to know what keeps others stay motivated about their life goals and how do they actually attain them in reality. It will help you gain insight into the process of appropriate goal setting and how to make things happen in a systematic manner. Isn’t it so?

  1. Why do you want to achieve your goals?
  2. What helps you stay motivated in trying times?
  3. Can motivation keep you mentally agile and fit?
  4. When was the last time you felt demotivated and why?
  5. Do you think that incentives can improve motivation?
  6. What reduces your motivation in no time?
  7. How long do you work in a day that takes you closer to your goals?
  8. With whom will you share your success story?
  9. How are interest and motivation connected to each other?
  10. What is holding you back from realizing your goals?
  11. Which one is better – to fail or never try?
  12. Why is goal setting important in life?
  13. Do you need a disciplined living to attain things that you’ve long wished for?
  14. How much help do you get from your partner in accomplishing your life goals?
  15. Are you satisfied with your accomplishments or wish to attain something more?
  16. How will you stop people who want to hamper your progress towards growth?
  17. Should you learn from your mistakes and start taking small steps towards growth?
  18. What is the difference between an achiever and a mediocre?
  19. Do you think that doing things differently than others can actually keep you ahead of time and help to accomplish goals?
  20. What impact can colleagues help on your work culture?
  21. Is motivation learned or innate? Your views please.
  22. Have you ever set an example for others to follow?
  23. Can life circumstances change life goals?
  24. What role did your parents play in setting your goals and aspirations?
  25. Do you feel that life will lose its purpose without an appropriate goal?

Take Away from ‘The Pleasant conversation’

We all want to have productive conversations that seem interesting and can continue for a long time. 

To develop deeper connections with new people or to improve your existing relationships, you need to know each other vividly. Only small talk may not suffice the purpose.

Sometimes you may binge-watch a TV show instead of talking to someone simply because you do not have a list of good and engaging questions.

Asking deeper questions is an art in itself. It doesn’t take a lot of practice but needs the skill to present the questions in the right way so that the conversation looks engrossing and captivating and can bust the boredom in no time.

Hopefully, you got an idea of what to ask someone in your next conversation and develop good relationships to stay for a long time.

Over to you now…..