150+ Personal Questions to ask a guy, Best Questions to know him!

Personal Questions to Ask a Guy

When you started liking someone and wanted to be part of his/her life, it can be challenging to get beyond the ordinary questions that everybody asks. That’s why we created a listing of personal questions to ask a guy. These questions are designed to know a person on a deeper and more personal level.

personal questions to ask a guy

personal questions to ask a guy

There is a lot of questions on deep-question.com. You can pick and select which of them you believe you should study because you know your guy better. Also, you might not need answers to some of the questions because you already know the answer.  Our website is full of different questions on different topics. If you have time, go through it.


Keep in Mind: When you are asking him something try to provide bit more information so that the other person can understand better.

List of Personal Questions To Ask a Guy:


  1. What was the best phase of your life?
  2. Would you give up a fun night time with your friends, to attend your unwell girlfriend?
  3. Do you enjoy two person outings or do you prefer group outings?
  4. Have you ever felt attraction for older women?
  5. Have you lost someone close to your heart?
  6. What it’s like growing up in your homeland?
  7. What is the most significant lie you’ve ever told?
  8. What is a deal breaker for you?
  9. Do you believe in open relationships?
  10. What is your biggest goal in life?
  11. What kind of work/activities gives you peace of mind?
  12. Where do you like to spend more time with your friends or with your relatives?
  13. How do you feel about yourself? Are you an introvert or extrovert?
  14. Do you have any siblings?
  15. What don’t you like about me?
  16. Do you believe in staying faithful to someone for whole life?
  17. Is what you’re doing now is same as what you always desired to do while growing up?
  18. If your ex-girlfriend wants to get back together, what would you do?
  19. Have you ever felt speechless?
  20. How many times in life did you encounter love?
  21. Do you prefer to read an e-book? Or the paper book?
  22. Do you think we should give cash to homeless people? Or we should tell them to go and work?
  23. What is the most embarrassing moment of your life?
  24. What was the worst phase of your life?
  25. What do you think of beautiful female friends?
  26. Who you prefer more and why? Your father or mother?
  27. What is the worst date?
  28. How adventurous are you? Give a few examples.
  29. What does your father or mother do for the living?
  30. What would you name your children?

30 More Personal Questions to Ask a Guy:

More personal questions to ask a guy

  1. What is your strangest habit?
  2. Are you financially stable? How stable are you?
  3. Are you spiritual? Do you believe in any religion?
  4. Are you aggressive?
  5. If you are in a horrific mood, do you prefer to be left on my own or have a person to cheer you up?
  6. What’s a great weekend for you?
  7. Who you want to be like in life?
  8. Have you ever had a death dream?
  9. Do you prefer to stay friends or with your ex?
  10. What do you do for work?
  11. Where do you want to be in the next five years?
  12. Do you have any interest in politics?
  13. What do you dislike about yourself?
  14. Do you believe in soul mates?
  15. Where and how dangerous do you notice both people as a couple in 5 years?
  16. What people always misunderstand about you?
  17. What’s the habit you would like to change in yourself?
  18. Are you satisfied with something that you don’t want to do it again?
  19. What is your best memory from the past?
  20. What is your preferred kind of female?
  21. What is the most awkward communication you have ever had with a person?
  22. What is the sweetest thing anyone has ever said to you?
  23. Have you had any crazy girlfriend story?
  24. If you could be something, what would you be?
  25. What is your most significant turn-on?
  26. Have you ever cheated on a female friend?
  27. Who is your favorite sibling?
  28. How did your bucket list look like for this year?
  29. What attracts you in me?
  30. What makes you irritated about others?

30 More Personal Questions:

More personal questions to ask a guy

More personal questions to ask a guy

  1. What has been your biggest blessing?
  2. What is that one thing, no one realizes about you?
  3. What is your biggest turn off?
  4. What is that one question you always refuse to reply?
  5. When was the last time you cried?
  6. What day you felt was the worst day of your life?
  7. Who usually stresses you out and who do you depend on to help you relax?
  8. What attracts you in a woman?
  9. What’s your biggest fantasy?
  10. With how many girls have you been in life?
  11. Do you get crushed regularly?
  12. What’s your favorite interest?
  13. What is the craziest habit you’ve removed from your life and would you do it again?
  14. What are you thankful for in life?
  15. What amazed you the most when you were growing up, but seems bizarre now?
  16. How would you describe yourself as a person?
  17. Have you ever mistakenly hurt someone?
  18. Do you have any feelings for your ex-girlfriends?
  19. What do you want to change in yourself?
  20. If a genie granted you three wishes right now, what could be your wishes?
  21. Faced any serious accidents?
  22. Do you believe in giving someone a 2nd chance?
  23. Did you ever write anything? E.g., journal, article, etc.
  24. What’s your most significant pet irritation?
  25. What makes you angry?
  26. If you have any superpowers, which one might you have and why?
  27. What is the worst thing someone can do to others?
  28. How would you rate me? On a scale of 1 to 10.
  29. What is the most useless thing you have ever seen?
  30. What’s your philosophy in life?

Next 30 Personal Questions to Ask a Guy :

Couple on personal questions to ask a guy

Couple on personal questions to ask a guy

  1. Do you believe in everything happens for a reason?
  2. What do you think about yourself, when you’re out of yourself?
  3. How do you spend your weekdays?
  4. What is something you always wanted to do but never had a chance?
  5. What kind of child was you in your childhood?
  6. Have ever you had your heart broken?
  7. Do your mother and father have a happy marriage?
  8. Have you ever tried to change the nature of your life?
  9. Do you have any enemies? Why?
  10. Are you a sensitive person by nature?
  11. What did your past teach you?
  12. Do you like a tattoo?
  13. Have you ever been seriously injured?
  14. Do you remember, when was the last time you broke someone’s heart?
  15. Where do you go when you want to be alone?
  16. When was the last time you seriously panicked?
  17. What are you most insecure about in your life?
  18. What makes you different from others?
  19. Is there anything you want to change in your own family?
  20. Have you ever wanted to be a female?
  21. Describe your perfect day?
  22. How do you feel about sharing your password with your life partner?
  23. What are your thoughts on Tinder?
  24. What is an ideal life, and how you’ll try and make it for yourself and me?
  25. What’s your favorite scene in a film?
  26. How do you know if someone is ready for marriage?
  27. What is your proudest accomplishment?
  28. What’s your biggest regret in lifestyles?
  29. Have you ever been arrested for doing any crime?
  30. What is your deepest, darkest secret?

Last 31 Personal Questions to Ask a Guy:

Love keychain on personal questions to ask a guy

Love keychain on personal questions to ask a guy

  1. What things you most likely to do on my own?
  2. Have you ever tried doing something unlawful?
  3. What was the worst lie which you told your mother or father?
  4. What consistently makes you disappointed?
  5. Who is that one person to whom you could speak whatever you want?
  6. What is your most considerable senseless worry?
  7. When everything seems to be going incorrect, how do you pick yourself up?
  8. What is something you recognize in people, but pay no attention?
  9. What lesson you always wished, you learned earlier in life?
  10. Tell me your best teenage memory?
  11. What does love indicate?
  12. What is your concept of a super vacation?
  13. What is that one element in me, which you would like to trade if given a chance?
  14. What is a controversial opinion? Do you have any controversial opinion on something?
  15. What are the stories that have made you, who you’re today?
  16. What truth do you try to ignore?
  17. Have you ever told a big lie and gotten away with it?
  18. Would you ever give a person a second chance, who cheated on you?
  19. Who is your celebrity crush from movies?
  20. Do you control strain easily?
  21. Do you’ve any close girl buddies, aside from me?
  22. What kind of relationship you have with your mother and father?
  23. Have you ever gotten into trouble?
  24. What was your biggest fear, when you were a child?
  25. What you notice in me, when we first met (be honest)?
  26. How would you react, if your parents didn’t like your partner?
  27. What always makes you angry?
  28. Do you’ve any phobias?
  29. When was the first time you appreciated a woman?
  30. What’s your favorite book of all time? And it communicates to you?
  31. Everyone has regrets about their past. Which regret would you like to exchange from your history?


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