48 Deep Conversation Starters To Know Someone Better

48 Deep Conversation Starters To Know Someone Better

48 Interesting Deep Conversation Starter Topics and Questions to ask to Know someone better

Just when we think we know a person, we are surprised with more revealing facts as we explore deeper.

Human personality operates on a very wide spectrum. We all have a lot of layers to our personality.

We have to dive deep and uncover the layers of their personality to reach to their core, to know him/her.

But in today’s fast paced digital life, we mostly end up having surface level communication that doesn’t go beyond surface level conversations like what’s up. Therefore most of our friendships and acquaintances are operating on a very superficial level.

We are perpetually faced with a paradox. We have a staggering number of friends and followers online but very few deep, authentic, intimate and fulfilling relationships in real life.

If we want to do away with this paradox, we will have to make the time and effort to get to know someone on a deeper level that go beyond the surface.

This definitely cannot be attained by using surface level conversations about the weather or latest fashion trends.

So here’s, a list of interesting conversation starters are compiled which can help you forge deeper and intimate connections with someone.


1. TOPIC – Metaphysics

Some of the most interesting questions that can take you beyond the surface level conversation and open up your horizon to the whole wide mysterious universe out there fall under the category of Metaphysics.

The term Metaphysics is a combination of two words “Meta”+ “Physics”. Here, Meta means over and beyond. So, the term implies over and beyond physics.

Metaphysics is the branch of philosophy that is concerned with understanding the essence and fundamental nature of things and principles that organize the universe.

It is concerned with questions like “What is the nature of reality?”

It comprises of all things abstract and intriguing like questions about life and death, parallel universes, alternate reality, time and space etc.

Here are few sample Metaphysics questions that you can try on to get started:

  1. Are you the same person you were yesterday?
  2. What is your notion of time? Are we affected by it, or does our consciousness create it?
  3. Do you believe in other dimensions or parallel universes?
  4. Where do we come from and what happens to us after physical death?
  5. Are there an infinite number of realities beyond our own where each possible decision taken is a different fork in the road traveled down?
  6. Do you believe in Déjà vu or synchronicity? Have you ever experienced it?
  7. Do you think that our mind just observes reality or can mind also alter reality?
  8. Do you think we create our own destiny or are we governed by fate?
  9. Do you believe in Out of Body or Near Death experience? Have you ever experienced anything like this?


The second categories of questions that can help you understand someone on a deeper level fall under the bracket of Love and romantic relationships.

2. Topic – Love

Love is the most sought after and yet most elusive human emotion.

We are mostly carrying unhealthy definitions of love from childhood fairy tales and Hollywood flicks.

The most common misconception propositioned by Hollywood flicks and childhood fairy tales about love is the notion that dependency is love.

In the romantic love ideal propositioned in these fairy tales, the delicate balance between intimacy and interdependence is lost and love borders on the psychological condition of codependency.

If we really want to forge a deep, authentic and intimate connection with someone, we have to be willing to have deeper conversations. This will help us find out if we are on the same page with the other person as far as our definition of love is concerned.

Here is a list of questions that can help you to understand someone’s definition of love better:

  1. Does being in love mean being independent, codependent or interdependent for you?
  2. Is love only a bio chemical response to specific set of stimuli?
  3. Is love a choice or a feeling?
  4. Do opposites attract or are like minded people more compatible in relationships?
  5. If you have to rank in order of preference: physical attraction, emotional compatibility, intellectual compatibility and lifestyle compatibility? What would be your order of preference?
  6. Should you change yourself for someone you love?
  7. Can you love more than one person at the same time?
  8.  Is it important to be best friends with your romantic partner?
  9. What is the most thoughtful gift that you have ever received or given?
  10. What’s your take on the forever and happily ever after?
  11. What’s the craziest thing you would do for someone you love?
  12. What is your love language? How do you express love and how do you want your romantic partner to express love to you?
  13. When you are feeling low, do you prefer to be left alone or would you like someone to cheer you up?
  14. When was your last relationship and how long did it last?
  15. Why do you think your past relationship ended? What did your past relationship teach you?
  16. Do you usually remain friends with your exes?
  17. Do you believe in a thing as soulmate, twin flames or kindred spirit?


3. Topic – Psychology

Psychology is the study of the human mind and behaviour.

50 Questions To Ask A Girl If You Want To Know Who She Really Is

50 Questions To Ask A Girl If You Want To Know Who She Really Is2

1. What’s one thing that’s happened to you that has made you a stronger person?

2. What’s one thing that’s happened to you in your life that made you feel weak?

3. Where is one place you feel most like yourself?

4. Where is your favorite place to escape to?

5. Who do you think has had the largest influence on the person you are today?

6. If you could change one thing about yourself what would it be?

7. If you had one day left to live, what would you do first?

8. What decade do you feel you most belong in?

9. Who are you closest to in your family? Why?

10. Who is the one person in this world that knows you best?

11. What is your favorite quality about your best friend?

12. When you were younger what did you think you were going to be when you grew up?

13. If you could identify with one fictional character (from a book, show, or movie) who would it be?

14. Do you easily accept compliments? Or do you hate compliments?

15. Is your favorite attribute about yourself physical or non-physical?

16. What is your favorite physical attribute about yourself?

17. What is your favorite non-physical attribute about yourself?

18. Do you believe in love at first sight?

19. Do you believe in soul mates?

20. How seriously do you take horoscopes?

21. Have you ever been in love? How many times?

22. What makes you fall in love with someone?

23. What does vulnerability mean to you? What has the ability to make you vulnerable?

24. What’s one thing you’re scared to ask a man, but really want to?

25. If you were a man for a day, what would be the first thing you do?

26. What do you find most attractive about each sex?

27. What’s one thing you’d love to learn more about?

28. What is something you’ve never done that you’ve always wanted to do?

29. Why haven’t you done it yet?

30. If money didn’t matter, what would your dream job be?

31. If you had off from work today, what would you do?

32. What was the last thing that made you cry?

33. What was the last thing that made you laugh?

34. What is your favorite memory?

35. What’s the last thing that REALLY embarrassed you?

36. What is your biggest fear?

37. Do you have any regrets? What’s your biggest one?

38. Have you ever broken a law? If you haven’t what is one law you’d love to break?

39. What is the craziest thing you’ve ever done?

40. Would you have a conversation with a stranger?

41. Would you tell a stranger they have toilet paper hanging from their shoe? Or their dress tucked into their underwear? (Or anything else that is embarrassing to be seen in public)?

42. What’s your favorite joke?

43. Are you a dog person or a cat person?

44. If you could be any animal, what animal would you be?

45. What’s one show, movie, or book, you’re embarrassed to admit you enjoy?

46. How do you think your parents would describe you as a child?

47. If you could go back to any age or time of your life, what age or time would it be?

48. What’s something you believe in that not everyone else does?

49. What’s one thing you would say that makes you unique from other people?

50. What is one thing you feel your life is missing?

50 Questions To Ask A Girl If You Want To Know Who She Really Is2

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40 Deep Questions To Ask If You Really Want To Get To Know Someone

40 Deep Questions To Ask If You Really Want To Get To Know Someone

Here are 40 deep questions to ask if you really want to get to know someone:


1. What’s your philosophy in life?

2. What’s the one thing you would like to change about yourself?

3. Are you religious or spiritual?

4. Do you consider yourself an introvert or an extrovert?

5. Which parent are you closer to and why?

6. What was the best phase of your life?

7. What was the worst phase of your life?

8. Is what you’re doing now what you always wanted to do growing up?

9. What makes you feel accomplished?

10. What’s your favorite book/movie of all time and why did it speak to you so much?

11. What is a relationship deal-breaker for you?

12. Are you more into looks or brains?

13. Would you ever take back someone who cheated?

14. How do you feel about sharing your password with your partner?

15. When do you think a person is ready for marriage?

16. What kind of parent do you think you will be?

17. What would you do if your parents didn’t like your partner?

18. Who is that one person you can talk to about just anything?

19. Do you usually stay friends with your exes?

20. Have you ever lost someone close to you?

21. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

22. What’s the ideal weekend for you?

23. What do you think of best friends of the opposite sex?

24. Do you judge a book by its cover?

25. Are you confrontational?

26. When was the last time you broke someone’s heart?

27. Would you relocate for love?

28. Did you ever write a journal?

29. What are you most thankful for?

30. Do you believe in second chances?

31. What’s the one thing that people always misunderstand about you?

32. What is your idea of a perfect vacation?

33. What did your past relationship teach you?

34. What are your thoughts on online dating or tinder?

35. What’s on your bucket list this year?

36. When have you felt your biggest adrenaline rush?

37. What is the craziest thing you’ve ever done and would you do it again?

38. If a genie granted you 3 wishes right now, what would you wish for?

39. What’s your biggest regret in life?

40. What do you think about when you’re by yourself?

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