Now Reading
300 Thought Provoking Questions to Make Conversations Interesting

300 Thought Provoking Questions to Make Conversations Interesting

Updated on Jul 01, 2022

Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling) , Life & Relationship Coach

300 Thought Provoking Questions for Interesting Conversations - Deep Thought Questions

What do you do when you know a person for a while but don’t know how to spice up the conversation with them anymore? Or it can be your first date where you have asked all the generic questions and there is an awkward silence for a little too long?

At parties or get-togethers, we run out of things to do or say and that makes all of us sweat. It is a little unfortunate but we all are afraid of looking uninteresting. In such situations, it is important to have a few thought provoking questions in your mind that you can fire to keep the conversation going.

These questions don’t always have to be serious. They can be fun too. They are perfect and much better than having a forced small talk.

300 Thought Provoking Questions to Make Conversations Interesting
300 Thought Provoking Questions to Make Conversations Interesting

What are thought provoking questions?

Thought provoking questions are mind musings that can set the mood of a conversation. It digs your brain with real substance; enables new ideas to thrive and fresh perspectives to grow.

When you think, it can be an array of ideas taking shape every now and then. At times, you may think about yourself, your childhood, or how your life would have been if you could do something else than what you are doing right now.

The thought provoking questions makes you contemplate, introspect, and question your human existence. Sometimes, these are random questions that can act as good conversation starters.

Some of these are philosophical questions, others can be personal and there are many that give you a good mental exercise. One thing is common in all of these and that it evokes pondering and rumination.

So, to break the ice or to break the monotony, here is a bucket list of thought provoking questions that can create interesting conversations.

300 Thought Provoking Questions

Deep Thought Provoking Questions to Ask

For the times when you want a conversation to have depth and substance, you must count on philosophical questions. These questions ensure that you know and understand a person from deep within.

They also ensure that you have interesting conversations. Sometimes, the answers to these questions can give you a new meaning in life. 

  1. Do you believe in destiny or you think life is in our control? 
  2. What do you think is the purpose of this life? 
  3. What do you think happens after death?
  4. Do you think there is another life after death? 
  5. Do you believe in coincidences? 
  6. Do you believe it when they say everything happens for a reason? 
  7. As human beings, what should be our topmost priority? 
  8. Should we all work towards one big goal? 
  9. If living in every moment is the right way to live life, how can we have a dream for tomorrow? 
  10. Who decides what is right and wrong? 
  11. Is this life a fragment of our imagination? 
  12. Should life be lived in ignorance or depth is needed to really understand life? 
  13. Do you understand life or you just live on auto-pilot? 
  14. Why do we expect others to love us the way we love? 
  15. Why do we judge others by their actions but expect them to judge us by our words? 
  16. What if the memories that we hold are not even partially true or real?
  17. What if we are absolutely wrong when we say we know someone inside out? 
  18. Is it possible for someone to be one person within but entirely different and opposite outside? 
  19. What are those things that you know are true but you still would like to avoid? 
  20. When do you feel like you are finding meaning in your life?
  21. Is it important to suffer in order to fully understand life? 
  22. Why do people who go through a lot of pain understand life better? 
  23. How is it possible for someone to hurt other human beings? 
  24. If every human being is different and is doing what their mind is telling them to do, how is this world still existing? 
  25. Is loving yourself enough a recipe for a happy life?

Thought provoking questions to start good conversations

  1. Do you set a goal in life? 
  2. Is success a societal construct?
  3. If death is the last resort, why do we live at all? 
  4. Is it important to give back something to society? 
  5. Do we really have to be social animals? 
  6. Can the psyche of a person be modified? 
  7. Does each individual’s word restrict to his or her psyche? 
  8. When people know that consciousness can make them happy, why are most of us still miserable? 
  9. Is pain really inevitable or our individual decisions put us in misery?
  10. Why do human beings sometimes believe things strongly when they can’t even be proved? 
  11. What can be called a waste of human potential?
  12. What is the best way to put our entire potential into use?
  13. Isn’t satisfaction bigger than happiness? 
  14. If there was no social construct and pressure, who would you be and what would you do?
  15. If you found out that there is life on other planets, would you feel threatened? 
  16. On a scale of 1 to 10, how satisfied are you with your life?
  17. Have you ever thought of taking your own life?
  18. What do you think will people say about you at large after your death? 
  19.  Do you ever think of starting your life all over again? 
  20. If you could go back in time, what mistake would you have rectified? 
  21. If you were to make a movie on your life, what would have been the title of it? 
  22. What stops you from doing what you really want to do? 
  23. Is it possible to wholeheartedly love someone without expecting anything in return? 
  24. Who are you when no one is watching? 
  25. To what extent can you go to avoid your fears? 
  26. Do you think about all the lives you are not living? Does it put pressure on your shoulders? 
  27. When do you deeply connect with someone? 
  28. What makes human nature complex?

Funny Thought Provoking Questions to Ask

Sometimes, we want the conversations to be light-hearted, feel good and funny. When everyone in the room is laughing because of something funny deep questions you asked, you feel a different kind of happiness.

So here are a few funny deep questions or funny thought provoking questions that you should keep in your mind while going to any get-together. 

  1. If you only had to ask two questions to someone to know them fully, what would be those questions? 
  2. What is your funniest memory of yourself? 
  3. What would be your first reaction if aliens arrived on earth? 
  4. Have you ever committed a blunder but no one ever found out it was you?
  5. Have you ever sent a message to someone about them that you were supposed to send someone else?
  6. What is the most embarrassing thing you have done in your life? 
  7. Have you ever waved at a stranger thinking they were someone you knew??
  8. What is that one situation where you wish you weren’t present? 
  9. Have you ever seen someone doing something that made you feel embarrassed? What were they doing?
  10. What is that one activity that you never want to witness people doing? 
  11. What rumor would you like to hear about yourself? 
  12. What conspiracy theory would you want to spread about?

Silly thought provoking questions

  1. What is the funniest thing you do when no one is watching? 
  2. Is there any thought that makes you laugh out loud every time you think about it? What is it?
  3. Is there anything that you thought was real but later figured out it was not?
  4. What is the stupidest lie you told someone? 
  5. Have you ever run away from a date? Why and how? 
  6. What according to you is the funniest way to live your life? 
  7. Who makes you laugh the most and how? 
  8. Have you ever told a story in a way that it made people laugh for minutes? What was the story? 
  9. What is the stupidest thing you did as a kid that you now regret?
  10. If you were arrested, what would your family and friends think you had done?
  11. What is the silliest thing you have said in order to feel and look funny?
  12. Do you remember the worst smell you have ever smelled? 
  13. Have you ever felt like laughing in a very serious situation? What made you want to laugh?
  14. What are your most useless thoughts? 
  15. Have you ever laughed on someone’s face? What was your reason? 
  16. What is the funniest way in which the internet has changed your life? 
  17. Have you ever watched something so funny that you couldn’t stop laughing for a long time? What was it? 
  18. What do you think can one day break the internet? 
  19. If you and your friend are in a lift with 2 other strangers, what would you say out loud to embarrass your friend?
  20. Can you think of a joke that can make anyone laugh? 
  21. If you had to appear somewhere in a funny attire, what attire would you wear? 
  22. If you got stuck in a room with two of your ex-partners, what would you do? 
  23. If you had to make a funny loud voice, what would it be? 
  24. If you were to give yourself a funny pet name, what would it be? 
  25. If you could become an animal, which one would you choose and why? 

Personal thought provoking questions

  1.  If you were given only 30 seconds to describe yourself, what would you say? 
  2. What are your three biggest achievements?
  3. What is that one thing about yourself that makes you really proud? 
  4. What is your biggest fear in life and how did you generate it? 
  5. What is the definition of love for you?
  6. If you were to die today by the end of the day, what would you do in the evening? 
  7. How do you decide if someone loves you? 
  8. Are you scared of death? If yes then why? 
  9. Is there anything that you are scared of losing?
  10. If you get to know that the world is ending, who would you want to run to and why?
  11. Does the person you love the most know that you love them? 
  12. To what extent can you go for the people you love?
  13. What makes you hate a person? 
  14. What makes you angry at yourself if there is anything at all? 
  15. What can someone do to make your day? 
  16. When do you feel like you are living your life to the fullest? 
  17. What are those three things that you absolutely don’t want to do in your life? 
  18. Would you like someone to comfort you with sweet lies or hurt you with harsh truths? 
  19. What can make you break the law of your life? 
  20. In this present moment, how do you feel about yourself and your life?
  21. When have you felt the happiest in your life? 
  22. Do you have a long term goal? What is it? 
  23. What do you appreciate the most about yourself and the person you love the most? 
  24. Who do you think you have hurt the most and how? 
  25. Is there something that you have not forgiven yourself for?
  26. What comes between you and your best life? 
  27. On a scale of one to ten, how interesting your life has been so far? 
  28. What is that one thing that you have experienced but don’t want anyone else to experience? 
  29. What is that one thing that makes you really sad? 
  30. What do you feel grateful for? 

Best thought provoking questions

Everyone likes to be a part of a stimulating conversation because it feels good and breaks the monotony. So, here is a list of a few open-ended questions that are great conversation starters.

  1. What is your hardest life lesson?
  2. With whom do you compare yourself the most?
  3. Are you excited about your new job? What makes you feel so?
  4. What is the one thing that you need to carry every day?
  5. Who inspired your life and living? Do you have a role model to look up to?
  6. Do you have any childhood experiences that did hurt you the most?
  7. What is the most beautiful thing that has happened to you till date?
  8. Are you emotionally overwhelmed? What makes you feel so?
  9. What are the three things for which you will feel grateful forever?
  10. What does ‘ideal life’ mean to you? Do you have one?
  11. Are you a person who prefers to ask many questions or do you settle for less knowledge?
  12. What new skills did you learn in the past year?
  13. Do you think that crying is a sign of emotional weakness?
  14. Do you judge yourself?
  15. Have you ever faced hardships? Did it make you strong?
  16. Do you believe in purposeful living?
  17. How comfortable are you taking risks?
  18. Do you think a good sense of humor is needed to maintain a good relationship?
  19. How do you measure peace of mind?
  20. Have you ever tried to commit a selfless deed that benefited others?

Good thought provoking questions

The good thought provoking questions can make you ponder and question anything and everything. These can initiate stimulating conversations between family and friends.

  1. Can money buy love and happiness?
  2. Do you like challenges or prefer to be in your comfort zone?
  3. What is that one best life lesson that you have learned from your parents?
  4. Can you think of one lovable memory that brings you an instant smile?
  5. Are you living a meaningful and purposeful life?
  6. What makes you feel ‘good enough’ and ‘empowered’?
  7. What impression will you try to give; you meet a childhood friend after 20 years?
  8. Do you harbor regrets?
  9. What was the worst advice that someone gave you?
  10. How do you measure a ‘good life’? In job success? In healthy relationships? In happiness? In living the moments fully? Or something else?
  11. Have you ever tried to break the law?
  12. If you are given a chance to go back in time; which year will you choose and why?
  13. How should one handle disappointments and setbacks in life?
  14. What is that one thing that you wish to change about yourself?
  15. Do you ruminate about your future life too often?
  16. Which is your dream holiday destination?
  17. Have you ever thought of solo traveling? Does it excite you?
  18. Do you fear failures? Why?
  19. What do you think, life is a matter of chance or choice?
  20. If you win a lottery, how will you choose to spend the money?

Interesting Thought provoking questions

To maintain an interesting conversation, you need some exciting questions that are worth talking about. These small talks can have an impact on your life and living.

  1. Do you have harsh truths about yourself? Do you ignore them? Why?
  2. What is that one thing that can make you angry at any moment?
  3. How would you define yourself as a person?
  4. Do you have phobias? What is it and why?
  5. What scares you the most?
  6. Do you believe in the ‘law of attraction’? Have you ever used it in your life?
  7. How do you treat and behave with people who cannot do any good for you?
  8. What is one past pain that you need to heal from?
  9. Do you lie to yourself? How and why?
  10. Are you exceptional or just mediocre?
  11. Which one do you think is easy? To love or to hate someone
  12. Is perfectionism a reality or a myth?
  13. What are the things that you still remember about your kindergarten school?
  14. Name four authors whom you admire the most?
  15. Technology has made our lives easier or tough. What is your opinion on this?
  16. What is the foundation of a strong and stable friendship?
  17. Can you measure kindness?
  18. How do you manage work pressure at home and at the office?
  19. What is that one mistake that you will never commit again?
  20. Who is that one person in your life with whom you prefer to share your secrets? 

Thought provoking questions about life

The deep thought provoking questions of life helps to see the various facets of life and living. These conversation topics can be really worthy to unfold the harsh truths and enjoy the present moments of life. Some great questions to start with are:

  1. Have you created the life of your choice?
  2. What is meant by ‘meaningful life’? Is it just a myth or reality?
  3. Do you pause and slow down to enjoy the tiny joys of life?
  4. How do you wish to live your life with gratitude or with pride?
  5. What is your deepest desire that still remains unfulfilled?
  6. What gives you ‘peace of mind’?
  7. Are you happy? If not, what is the source of your unhappiness?
  8. Who supports you the most in times of difficulties?
  9. What is your life’s mission? Have you accomplished it or are you trying hard to do so?
  10. Do you enjoy moments of solitude? When was the last time you were alone?
  11. Do you believe that all of us possess some good qualities?
  12. How would your life be 10 years from now?
  13. How do you solve conflicts?
  14. Are you assertive or aggressive in solving life’s problems?
  15. What is the craziest thing that you did till now?
  16. Do you believe in life after death?
  17. Name your greatest fear. Why is it so?
  18. Do you ‘exist’ or ‘live’?
  19. What irritates and annoys you the most?
  20. Do you think that your life is worth living?

Thought provoking questions about diversity

When we talk about diversity, it means diversity in the workplace, diversity in culture, or classrooms or even diversity in the ecosystem that we live in.

These questions and answers delves deeper into the diversity and inclusion program that every development initiative looks into.

  1. What are your thoughts on diversity and inclusion? Do building inclusive teams make employees feel safe?
  2. Are you a diverse individual who is aware of cultural transformation to build an inclusive and cohesive workforce?
  3. What, according to you, is the primary drawback of working with diverse groups of people?
  4. What are your thoughts on biodiversity? Does it make our planet beautiful?
  5. Does biodiversity help in maintaining ecological balance?
  6. What is your point of view on diversity in classrooms? Does it improve learning and enhances performance?
  7. What are the benefits of diversity and inclusion programs?
  8. How can a teacher make changes in the classroom set up, so that every child feels included?
  9. Does diversity and inclusion programs facilitate employee participation in an organization?
  10. Are good leadership teams diverse and inclusive in nature?
  11. Are the organizations looking for best practices in diversity programs?
  12. Does bringing people together from diverse cultural backgrounds reinforce work performance and an overall turnover of the organization?

Thought provoking questions for couples

The conversation starters for couples need to be interesting, motivating, and stimulating to keep the spice alive. At times the fun questions for couples are mind tickling that can build long term relationships based on mutual love, trust, and understanding.

  1. What is that one thing that you liked about my body?
  2. What are your expectations from marriage? Do you believe in marriage vows?
  3. Who was your first crush?
  4. What are the things you wish your life partner should possess?
  5. Do you feel uncomfortable talking about sex and physical intimacy?
  6. How much bank balance one should have before starting a family? Any thoughts on it?
  7. What can we do to strengthen our friendship before we settle down?
  8. What are your thoughts on budget and financial planning? Do we need it?
  9. Can marriages ever be perfect? Any thoughts that you would like to share.
  10. Would you be comfortable sharing your deepest feelings, when you meet your would-be spouse for the first time?
  11. What was the most life challenging situation that you came across and how did you overcome it?
  12. How good was your childhood?
  13. Have you ever experienced a broken relationship?
  14. Which song did you hear dozens of times?
  15. If you are given $1000 to spend on yourself, what will you do with the money?
  16. What is the best gift that someone gave you?
  17. Describe the perfect honeymoon that you wish to have?

Deep thought provoking questions about relationships

Now we have another list of questions about relationships that makes you think about your available choices and best decisions.

These conversation topics for couples help to know each other well and foster deeper connections. As it is essential to know your partner well, these questions are worthy to delve deep into the subconscious mind.

  1. How do you spend your free time during weekends?
  2. How do you manage unexpected guests in your home?
  3. Which behavior of your partner that you will never tolerate?
  4. Is it good to forget or forgive in a relationship? Which one will you choose?
  5. What hurts you the most? Do you have any harsh truths about friends or family that you still remember?
  6. What will your perfect date look like? Are you the one who respects long term relationships?
  7. Are you jealous of someone in your life?
  8. When was the last time you had a burst of laughter that you still remember?
  9. What makes you happy and secure from within?
  10. Do you like surprises?
  11. Which part of your body makes you proud?
  12. What are your crazy and foolish pet peeves?
  13. How do you prefer to celebrate your achievements?

Thought provoking questions to ask on a date

Your first date is a special one and you would prefer to be in your best self. This can happen if you manage to initiate and maintain an interesting and free flowing conversation.

  1. Who is your favorite celebrity crush?
  2. Which is the most embarrassing moment of your life till now that puts you in shyness?
  3. Which childhood memory would you cherish for a lifetime?
  4. Which ice-cream do you prefer to see at the dinner table?
  5. What will you wear on your first date night?
  6. Do you like road trips?
  7. If you are told to make a movie about your life; which timeline would you prefer to portray?
  8. Are you a cleanliness freak?
  9. Who is your best friend and why do you think the person is dear and special to you?
  10. Would you like to go bungee-jumping or skydiving?
  11. Do you like adventure sports such as river rafting?
  12. What is your most weird talent?
  13. What is that one thing that nobody knows about you?
  14. Are you a bookworm or a movie bug? 
  15. Are you extravagant?
  16. Are you a morning bird or night owl?
  17. Do you like sweet desserts or salty snacks?
  18. Describe your happy space and peaceful abode?
  19. What human trait should your would-be spouse possess?
  20. Do you like tattoos? Would you prefer to have one?
  21. Which one is your favorite season and why?

Thought provoking questions for kids

The best way to understand a young child’s mind is by asking questions. You should aim to ask open-ended and intriguing questions that prompts and provokes them to engage in healthy discussions.

  1. Which TV show do you like the most and why?
  2. Which is your favorite band in high school?
  3. Which personality traits make you different from your classmates?
  4. Do you wish to write a book when you grow up?
  5. Do you enjoy the company of family and friends?
  6. Who is your favorite fictional character?
  7. Will you ever cheat on a test when nobody is watching you?
  8. Who loves you the most in this world?
  9. Name your five favorite toys
  10. What do you like about your best friends?
  11. Do you like ice-creams or chocolate more?
  12. Who hugs you the most when you feel sad about something?
  13. Do you fear dark rooms?
  14. Which is your favorite sport?
  15. Who is your favorite cartoon character?
  16. Who sets rules for you at home? Do you follow them?
  17. Have you ever been kind to someone? What have you shared with them?
  18. What are the three things that you wish to do during the summer holidays?

Thought provoking questions to ask a girl

A good conversation always leads to a deeper understanding of relationships. You need to ask questions that really matter to know each other well.

  1. Which family member has the most impact on your life?
  2. How much time do you spend on social media?
  3. In order to feel good; what is the first thing that you do to start your day?
  4. Have you found your dream job?
  5. What piece of advice will you give to young children?
  6. What is the most tragic incident that you have ever experienced?
  7. What are your views on arranged marriage?
  8. Have you ever protested or disagreed with your boyfriend’s views?
  9. Do you have unfulfilled dreams that you still wish to pursue?
  10. What are your secret wishes?
  11. Are you rude or humble?
  12. What do you like about your home and family?
  13. What are your views on destiny?
  14. Do you believe in keeping promises? Have you ever broken a promise?
  15. Whenever you are in a messed up situation; whom do you look up to for help and guidance?
  16. Do you hide your emotional side?
  17. Are you committed to anything in your life? What is it and why?
  18. Do you feel depressed when things do not work your way?
  19. Has life ever been harsh on you? How did you manage yourself emotionally?

 Closing thoughts 

A great question is the one that makes people pause, think, and wonder. We spend hours just talking about things that probably don’t matter then why shouldn’t we make use of thought provoking questions that can make any conversation interesting?

You can be on a date, at a party, or in a get-together, the aforementioned questions curated by us will refresh the mood of all your friends and family. You must choose the type of thought provoking questions wisely depending on the setting that you are in.

If you think deep and philosophical questions can make the party a little slow for your taste, you can always go for fun thought provoking questions.

The answers to those questions are always going to leave people smiling and laughing. So, engage your friends and family in a tasteful manner from now on. Let them have a wonderful time.