Deep Questions to Ask a Guy

Deep Questions to Ask a Guy
By Subhash Das Updated

“Please tell me more deep questions to ask a guy, I want to know my guy more” – This is probably the monologue of every other girl for her guy. We all want to know every aspect of our beloved persons. This is a fact that can not be denied. In order to know the person, there is nothing better than asking him some deep and meaning questions. Now you might be thinking of what can be the types of deep questions?

Deep or thoughtful questions mostly have philosophical touches. At times, these questions can be really dark and sensitive. You may unfold some of the deepest truths of his life. In fact, why not? After all, a healthy relationship should not have any secret.

100 Deep Questions to Ask a Guy: Unravel the Secrets

The below questions have been prepared, keeping every unforeseen situation in mind. Here, a list of 100 deep questions to ask a guy has been curated. So, are you ready to unravel the mystery? Let us jump to the details.

  1. Is there any ideology that you believed in past, but now you find it obsolete and unrealistic?
  2. Has the activity of your role model ever hurt you?
  3. If someone asks you to pick one of your biggest negative aspects, then which one would you talk about?
  4. Who is the person in your life whom you admire the most?
  5. What is the one thing you always wanted to talk about but never got a chance?
  6. Do people’s judgments hurt you?
  7. If you were a leader, then what are the things you could have done to eradicate poverty in our society?
  8. Do you take criticism seriously?
  9. What are the things affect your body, mind, and soul occasionally?
  10. How important is it to forgive someone?
  11. What is the one thing you would love to do after a few years?
  12. If someone asks you to motivate your parents in their distressful times, then what are the real-life examples would you cite?
  13. What have you learned from your past relationship?
  14. Do you think that your every past activity was well executed and thoroughly justifiable?
  15. How would you convince your parents if they do not let you marry your love?
  16. Who is the person in your life whose lose deeply affected you?
  17. Many people believe that the young generation has no morality. As of one of the representatives of this youth society, what is your opinion on it?
  18. If your partner ever wants you to change yourself, then would you do that?
  19. Intentionally or unintentionally have you ever broken anyone’s heart?
  20. If you become the President of your country, then what are the reform movements would you start?
  1. Is there anything you hate about your country?
  2. What is the one thing people find interesting about you, but you personally are ignorant of that?
  3. What are the things you notice at first in a stranger?
  4. Are you a narcissist?
  5. When was the last time, you had a serious adrenaline rush that you became almost petrified?
  6. Honesty is always the best policy– what do you think of this old adage?
  7. Have you ever taken any compulsive decision in your life that accidentally became clicked?
  8. What is the book you can read ceaselessly without feeling bored?
  9. If your 3 wishes get a grant, then what would you long for?
  10. Whom do you love and respect the most between your parents?
  11. What are the things you do to motivate whenever you feel disturbed?

Thoughtful Deep Questions to Ask a Guy

  1. Do you believe in supernatural powers?
  2. Do you believe in Karma, that action and reaction follow each other?
  3. Have you witnessed anything that has changed your life forever?
  4. On a beautiful morning, if you find that last night suddenly a war broke out in your country, would you go to serve your country in that fretful situation or would you just try to flee a safer place?
  5. If someone takes advantage of your good morale, then how would you tackle the situation?
  6. There is a famous adage that everything is fair in love and war – What is your take on that?
  7. Do you believe in sharing everything with your partner?
  8. What is the best quality of yours, that very few people have?
  9. Is there any white lie that you often tell people?
  10. Would you be with your partner if you find that she is drug-addicted?
  11. What is the best piece of advice you have ever been provided?
  12. Are you an introvert or an extrovert?
  13. On a lonely night, if you find that few people have attacked a helpless person with some sticks, then what would you do to save him or would you just flee from the place?
  14. What is the one good thing about you that even a stranger would understand?
  1. Are you happy in your life?
  2. Is there anything that could have made you more self-confident than what you are today?
  3. Is there anything that exceptionally good about your parents?
  4. If you have ample amount of money, then how differently and wisely would you lead the life?
  5. Do you save money or just love to be extravagant?
  6. If you find a cheap version of anything luxurious, then which one would you choose and why?
  7. Are you a liberal or a political person?
  8. Have you ever seen that psychopathic traces in a child?
  9. Many say that soon something would destroy our planet Earth, do you think like that?
  10. Who is the most punctual person you have ever met?
  11. Which culture attracts you the most?
  12. A person without self-confidence is nothing but a bunch of straw – do you think in the same way?
  13. On a very bad day, when your mood is already swinging up and down; if someone passes critical remarks about you. How would you react?
  14. Have you ever told anyone to taste an ugly looking food that turned out to be great?

Interesting Deep Questions to Ask a Guy

  1. Do you ever fake your personality just to showcase an artificial you?
  2. Has anyone ever rebuked you in spite of doing some good job?
  3. What is the biggest risk you have ever taken in your life?
  4. At times, we see reports of self-killing on newspapers. What is your take on Euthanasia or Self-killing?
  5. Have you ever heard of mercy-killing? What is your opinion on that?
  6. How long do you take usually to understand a certain person and personalities?
  7. Is there anything you always wanted to tell your ex but you never got a chance?
  8. Do you follow any principle in life or just love to go with the flow?
  9. Have you ever met anyone through Tinder?
  10. What is the most bizarre thing you experienced on your first date?
  11. What is the thing you respect the most about your best friend?
  1. Do you ever judge your friends in a wrongful manner?
  2. If you have any grudge against a particular person, then would you tell him directly?
  3. Have you ever faced any controversy or criticality?
  4. What is the most brilliant reply you have ever given to a stranger?
  5. So, many people say nowadays, that people have lost humanity. What is your take on that?
  6. Eyes don’t lie, right or wrong?
  7. If your best-buddy openly lies about you, then would you confront him/her openly or just take some time to understand the motive?
  8. So, has anyone ever cheated you?
  9. What is the one thing you want to carry with you in an unknown place?
  10. Which app do you hate the most?
  11. Technology has some negative aspects too, do you think similarly?
  12. What is the best thing you have learned from mother Earth?
  13. If you are lost in a country where the people can hardly speak your language, then what would you do in order to reach home safely?
  14. Do you believe in lucky charm?
  15. What are the things you usually do to defend yourself?
  16. Is there anything that you repeatedly do but always realize that you should not do that?
  17. What is the most adventurous thing you have done that very few people know about?
  18. Do you consider yourself philosophical?
  19. Is there anything still haunts you?
  20. Have you ever saved anyone from suicide?
  21. Who is the person in your life, whom you have never acknowledged in spite of knowing the truth that the person has been with you in every thick and thin?
  22. Some are rich whereas some are poor, don’t you think this is disproportion? Because everyone has the right to live with equal amounts of wealth.
  23. If you could inject one idea in everyone’s mind, what could it be?
  24. Why do you think that the life of a human being is precious?
  25. Do your parents support you in every situation? Have you faced any opposition from them ever?
  26. Which movie has changed your life forever? And the movie is so amazing that you often refer it to others.
  27. Last time, when did you cry just like a baby? You just completely forgot your surrounding?
  28. What is the best thing about your country?
  29. So, have you ever experienced anything bizarre in your childhood?
  30. If you wrote the anthem of your country, what could have been the first line of the song?

Meaningful Deep Questions to Ask a Guy

So, this was the list of top 100 deep questions to ask a guy. Deep questions often make people very emotional, so if you feel that he gets depressed in between the discussion, pacify him with some motivating words. Things would become absolutely amazing if you can embrace him with passion and positivity.  Surely, the bonding between you two would not only enrich but will touch a new level.


  • Deep questions are always risky and can unfold many dark secrets. So, whenever you want to ask these things to him, you should always prepare.
  • Make firm eye-contact with your man, to show your trust and interest in him.
  • Do not ask him unnecessary dark questions about his past.