160+ Deep Questions to Ask

Human beings are thinking creatures. While we spend a lot of time talking about extremely superficial stuff, there are times when we start thinking about the bigger picture: the universe, our role in it, life after death, and so on. It is often thought that you get to know a person better when you ask them deep questions. Now where can you find a set of deep questions to ask anyone? Right here!

Deep questions offer a chance to have an amazing conversation and know each other in a much more intimate way on a deeper level. It makes your bonds become stronger and last longer. Delve deep into the questions we have prepared for you and get to know yourself and the people around you better.

Deep Questions for A Conversation With Your Best Friend

There is something special about best friends. We aren’t born with them like our siblings and relatives. We chose them and choose to be with them despite facing a lot of difficulties. This is what makes this bond so special. You can make this bond even more special by asking them these deep questions that we have curated specially for you.

1). What do you do when you get anxious?

2). What is something that makes me extremely happy?

3). Do you have something that you would want to tell me?

4). How well do you think you know me?

5). What food makes me happy instantly?

6). What is my go-to activity when I get sad?

7). What is the most fun moment you have had with me?

8). Who is the one person in your life who inspires you? Why do they inspire you?

9). How willing will you be to help a stranger in the middle of nowhere?

10). What is more important according to you: riches or fame? Why do you think so?

11). What is a moment you experienced in your life that still makes you have goosebumps whenever you think about it?

12). What is something that you regret in life? Why do you regret it? Do you think your life would have been any different if you could change that decision?

13). Who is the one person in your life who you see and think that you are lucky to have them?

14). Will you ever go away from the side of someone who needed your help at that moment?

15). What is your ideology in life? What is the foundation of the same?

16). If someone tries to fill you with lies regarding us, what will your first step be?

17). What is something that you see and think you have been blessed with?

18). Who is the one person who has the most influence on your thoughts?

19). What is something that you have learnt about life that you would like all of your generations to know?

20). What is an irrational fear or phobia you have that you want to get rid of?

21). Who is someone that you tried to please a lot, but were never successful?

22). What is something that you have that makes people like you?

23). What is something that you have that drives people away?

24). How will you tackle the situation if you ever found out someone was accusing you falsely?

25). How good do you think you are at reading people’s minds?

26). What is something that fills you with happiness?

27). Have you ever deliberately kept something from me? Why did you do so? Do I still not know that?

28). When you start talking to someone new, what goes through your mind?

29). Have you ever seen someone trying to cheat you?

30). What is something that has been taught to you by your earlier relationships?

31). What leadership qualities do you think you possess?

32). How gullible do you think you are?

33). What kind of a relationship do you have with your family?

34). Are you happy with where you are in your professional life?

35). Are you happy with where you are in your personal life?

36). How do you feel about me being your best friend?

37). Who is someone you think is directly responsible for helping you achieve whatever you have achieved in your life?

38). How proud do you feel when you think about yourself?

39). Do you like the work that you do?

40). What is something that you want to alter about your personality?

41). Who is the one person that you can trust blindly?

42). Where do you see yourself in the future? Am I still your best friend?

43). How much will you rate your trust issues out of 10? Why do you have these trust issues?

44). What is the most adventurous thing you have done?

45). What is the most soul fulfilling thing you have done?

Read also: 101+ Cute Things to Say to Your Girlfriend

Deep Questions You Should Be Asking Yourself

While we did make most of these questions for you to ask other people, there are some questions you should be asking yourself too to get to know yourself better and live a better life.

1). Am I judging people a lot in my life?

2). What are my most visible weaknesses?

3). What are my best strengths?

4). Have my actions directly or indirectly hurt anyone today?

5). What more can I do for myself so that I can keep growing?

6). Have I been immature in my decisions lately?

7). Am I being a good neighbour for people around me?

8). Have I been losing my temper too much?

9). Am I doing the right things and walking on the right path?

10). Am I on the path to achieve success in my life?

11). Am I correct in my definition of success?

12). What does happen after death? Does one gets reborn or does one perish on hell or heaven?

13). What makes life so valuable?

14). Am I happy with the work I am doing?

15). Is there a way to be alive after dying?

16). What will happen when my emotional support suddenly decides to leave me?

17). How do I shape my life as I go forward?

18). Should I be humbler or should I be more narcissistic?

19). What is the one that that makes me completely nervous and very anxious?

20). Are my actions the best I can do?

21). How can I not let anyone stop me from reaching the goals I have for myself?

22). How close am I really to achieve what I want in life?

23). Is there a true love for everyone? Are there soulmates? Have I found mine yet?

24). Am I being too hungry for money or not hungry enough?

25). Who is someone that is radiating a lot of negative vibes currently?

26). What else should I change or do to myself to become a better human?

27). What will I do if my close ones refuse to give me support?

28). What if one day I am in dire need of help and no one comes to my support?

29). Have I ever helped anyone when they were in dire need of my help? Did I help them to the best of my abilities?

30). How do I get rid of these misunderstandings in my life?

31). What are the right choices for me in my life right now? Am I making them correctly?

32). Have I hurt the people I love around me? How do I make up for it?

33). Have I ever hurt my parents by my actions? How do I correct my mistake?

34). Do I need to voice out my opinions more?

35). Do I need to speak for myself more?

36). How can I ask other people to love me when I don’t even love myself?

37). Am I ignoring my gut feeling? Should I listen to what it says?

38). Am I a prejudiced person at my heart?

39). What would happen if I die tomorrow? How would people react?

40). What are the things that are positive about me?

41). What are the things that are negative about me?

42). What kind of vibes do I generally give off?

43). What are some habits that I need to inculcate in my life?

44). Am I self-independent enough or do I need to be more self-independent?

45). Do I let go of my anger too easily?

46). Do I let my anger get the best of me?

47). Am I really treating everyone right?

48). Do I think too much about the outer beauty of other people?

49). What can I do to motivate myself more?

50). How well am I handling my failures?

51). What I fail in my goal right before achieving it? How will I be able to handle it?

52). How well am I at facing unprecedented challenges?

53). How well am I at handling pressure situations?

54). Who is the one person who is extremely important in my life?

55). Am I offering help to the people around me?

56). What will happen if I actually become successful?

57). Am I as selfless as I think I am?

58). Will I be able to influence the world in a good way? Will people remember me when I am gone?

59). Will I be able to become the best in my field?

60). Do I over think too much and confuse myself unnecessarily?

Read also: Questions to Ask A Girl

Deep Questions for A Conversation With Your Partner

When you pick a partner for yourself, you pick them because they are often the best person for you. And what better way to get to know your partner better than by asking them a bunch of deep questions.

1). What were your feelings when you saw me for the first time?

2). What were your feelings after our first meeting?

3). How do you define love?

4). Do you or did you ever believe in the concept of love at first sight?

5). What is the best thing about our relationship?

6). What makes you trust me this much?

7). What is the worst thing about our relationship?

8). Do you think I will ever cheat on you? What do you think will you do if that happens?

9). Do you think you will ever cheat on me? What do you think I will do if that happens? What do you think I should do if that happens?

10). What is something that makes us click together?

11). What is something that makes us different from the other couples?

12). What is something whose smell drives you crazy?

13). Will you ever take part in any illegal activity? Why do you think you will do so?

14). Will you break any rules for me? How far are you willing to go?

15). How would you react if someone stopped you from doing something you like? What if that person is me?

16). What is something you have done that you will never forget?

17). What is something that makes you an exclusive person?

18). What makes you so damn amazing and cool?

19). What is a way that guarantees instant happiness for you that I don’t know about yet?

20). What is something that you only want to share with me?

21). Do you have any alter-egos? What are they?

22). If you were told to live on an isolated island alone, what would be your reaction?

23). If you had to pick one person to live with you, who would you pick?

24). Do you think people can live alone? Without any connections or love? What do you think about that kind of a life?

25). Do you think you have a good enough balance between your personal life and professional life? What makes you keep such a balance and what would you hope to change?

26). Who is the one person that has been extremely influential in your entire life?

27). How important do you think outer beauty is?

28). Is there anything that you wanted me to know but never told me? Why did you not tell me? Do you want to tell it to me now?

29). Is there anything that you wanted to ask me but did not? Why did you not ask me? Do you want to ask me now?

30). If I ever act suspicious, what will your course of action be?

31). If anyone ever blames me for something in front of you behind my back, what will you do?

32). Do you want to change anything about me? What is it? Why? How would you change it?

33). Do you want to change anything about us? What is it? Why? How would you change it?

34). What is one thing that made you fall in love with me?

35). What is something that someone forced you to do but you really did not want to? Who forced you to do it?

36). Are you really happy?

37). What keeps making you take decisions for the good of others?

38). What is house of your dreams?

39). What is something that you would rather not do with me?

40). What are you with others: extrovert, ambivert, or introvert?

41). What is a life lesson that you would like all of your future generations to know?

42). How many children do you think form an ideal family?

43). Did your parents take good decisions for you?

44). What is something that your parents did but you would never do as a parent?

45). How good a parent, do you think you will be?

46). How do you know if you are successful?

47). What will make you think that our relationship has been successful?

48). What are some of the ground rules or base parameters in every relationship?

49). Do you think we both will last the distance? How do you see us separating, if at all?

50). What is something that you really love to do but is generally considered a bad thing?

51). What is the most badass thing you have ever done?

52). Do you have any wish that you have kept a secret from me? What is it?

53). What is the cutest habit you had as a child?

54). What is something that happened to you that changed you completely? In what way did it change you? Do you think there is still some of that old self left in you?

55). Do you believe in the fact that ends justify the means?

56). Have you ever felt lonely during our relationship?

57). Have you ever felt like breaking up with me? Why did you feel so? What convinced you not to break up with me?

58). Do you have any crazy thing in your bucket list? What is it?

59). What would you do if there was a global apocalypse tomorrow?

60). What would you do if I died tomorrow? How quickly would you move on?

61). Do you believe in marriage? Do you really think it makes a relationship stronger?

62). Who is the first person on your speed dial in case of any emergency?

63). What do you do when we have a fight and don’t talk?

64). What do you think of my parents?

Tips and Tricks

Knowing what questions to ask is one thing but knowing how to ask them and how to carry the conversation along is another. Because these questions are so deep in nature, they have a chance of going horribly wrong if not asked well. This is why we have some tips and tricks for you to keep in mind when asking people these questions.

Do not dwell in the past: Do not use these questions to dig into the past life of someone, especially when they don’t want to. Use them well.

Do not be forceful: If someone does not feel like answering your question, do not force them to answer it. There may be deep and dark reasons behind them which are best left alone.

Be prepared with your answers: As is the case with most kinds of question and conversations, the questions you ask will most definitely be asked back to you. So be prepared to give an answer. But for the most authentic experience try not to prepare your answer from before. Ride the flow and answer accordingly.

Be compassionate: A lot of these questions possess an emotional backdrop and even other questions can lead to emotional stories and experiences. Be compassionate to the other person, respect their feelings, and lend them your ears for their stories, and your shoulder for their head.

The best part about these questions is that while they are categorized into 3 categories, you can ask most of those questions to most people by changing the words a little bit. This helps you in striking up a deep conversation with your other friends or even your crush. Make sure you do not start asking these questions one after the other like a quiz show or mechanically like an interview. A deep conversation can perform miracles when executed well.

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