20 Questions to Ask a Guy

20 Questions to Ask a Guy
By Subhash Das Updated

Knowing a person always very intriguing and interesting; things become really easy when you have the right set of 20 questions to ask a guy. Every person has own ideologies and thoughts. And, it is not necessary that two individuals would believe in the same principles, but the deadliest pair becomes reality only when your vibe matches with the intended person. So here, we have curated the best 20 questions to ask a guy from different subject lines. These are the questions that you must be interested in knowing about him especially if you really like the person.

20 Questions to Ask a Guy about His Personal Life

20 Questions to Ask a Guy about Personal Life

It is the personal life that explores a lot of interesting facts about an individual. Just the perfect set of questions has the ability to draw all the important info. The following 20 questions to ask a guy about his personal would help you to define an outline about the person for sure.

  1. Ambivert, Introvert, or Extrovert – How would you define yourself?
  2. What is your biggest regret in life?
  3. Whom do you love and respect the most between your mom and dad?
  4. What is your daily schedule?
  5. How do you spend your holiday?
  6. Whom do you consider your role model?
  7. What do you do when you feel extremely anxious?
  8. If you are ever asked to share your biggest achievement till date, what would you name?
  9. How would you describe your childhood in one sentence?
  10. Have you ever felt inspired by any mythological character?
  11. Did you like studying ever?
  12. What is your dream job?
  13. How did you meet your best friend?
  14. Who understands you really well, in fact, more than yourself?
  15. Which countries would you like to visit within the next 5 years?
  16. How many languages do you speak?
  17. Is there any constraint that you have faced in your professional life?
  18. One thing that you enjoy with your parents only.
  19. Do you consider yourself a privileged person?
  20. What is the most amazing thing about your life?

[ Read: Personal Questions to Ask a Guy ]

20 Questions to Ask a Guy about His Interests

20 Questions to Ask a Guy about Interests

The person whom you like, you would definitely want to know the interests, likings, and dislikings of the individual. Interests of two people might match, even might not. But, it feels the best when you know everything about the opposite person and thus, we have presented a set of 20 questions to ask a guy about his interests and attachments.

  1. What is your morning call?
  2. Indoor games or outdoor games – which one is your arena of interest?
  3. Do you love reading books?
  4. Which type of food is your absolute favorite?
  5. Do you love watching movies?
  6. Netflix or Amazon Prime – Which one do you find more interesting?
  7. Name two of your current television shows.
  8. What is your favorite genre of movie?
  9. Who is your favorite author?
  10. Which book do you find pretty interesting?
  11. One cuisine that always makes you super happy.
  12. Are you a tea person or a coffee person?
  13. What is the one thing that is your biggest turn on?
  14. Is there anything that compels you to think something bad about the other person?
  15. How do you judge a person?
  16. How many scores would you give your character?
  17. Which shirt in your wardrobe is the oldest?
  18. Do you love shopping?
  19. How would you describe your friends?
  20. How many nicknames do you name and which one is your absolute favorite?

20 Questions to Ask a Guy about Relationship

20 Questions to Ask a Guy about Relationship

The relationship or bonding that a person shares with the other people always says a lot of unknown and unique things about the person. It explores a whole new personality and the perception of the intended individual. Check out the following bunch of 20 questions to ask a guy to know his past and present relationships, his equation with his friends, and many other amazing factors.

[ Read: Questions to Ask a Guy Over Text ]

  1. Do you have any childhood crush?
  2. How many scores would you give to your romantic side?
  3. Will you ever change the name or surname only if your girlfriend asks?
  4. What is the foundation of a healthy relationship according to you?
  5. Have you ever felt something special for your best friend?
  6. Is there any celebrity whom would you like to date at least once in your life?
  7. Can you share one memorable incident from your first date?
  8. What is the one thing, according to you, that every girl loves to be gifted?
  9. So, what is the biggest compliment you have ever received on your first date?
  10. What do you think of Tinder or any other dating app?
  11. One food that always makes every girl happy especially when meeting for the first time.
  12. What is the name of the most beautiful girl that you met in your high school?
  13. What is the one topic that you totally avoid on the first several meets?
  14. If life gives you another chance, which dating would you like to fix?
  15. Have you ever been asked anything horrible or awkward questions by an attractive girl?
  16. Do you believe in the institution of marriage or courtship?
  17. How do you dream your life with your partner?
  18. Do you consider beauty a parameter in relationships?
  19. What have you learned from your past relationship?
  20. Do you think that it is possible to be a friend with your ex even after a terrible breakup?

Intimate 20 Questions to Ask a Guy

Intimate 20 Questions to Ask a Guy

Intimacy is a part of any relationship and it is not always related to erotic things. There are other aspects as well that defines how seriously the person takes his bed game. The 20 questions to ask a guy that are presented here are all have a subtle perspective and not very erotic or sharp on the outer layer.

  1. At what age, did you first kiss?
  2. Have you ever kissed the hottest girl in your classroom?
  3. Do you check women by their shape and size?
  4. What feminine thing attracts you the most?
  5. Are you someone who is all about physical relationships?
  6. When did you lose your virginity?
  7. Romanticism and intimacy – how related these two are with each other?
  8. Has anyone ever caught you while doing something naughty?
  9. What is the most fascinating thing about a woman?
  10. Have you ever fantasized any random person?
  11. Would you ever double date anyone or have you double date anyone before?
  12. Have you ever kissed your crush?
  13. Do you want an amazing erotic life or a great and passionate romantic life?
  14. Are you someone who takes foreplay pretty seriously or just a great bang-bang is enough to satisfy you?
  15. Last time, when did you have an amazing bed game?
  16. If today you come to know that I have a crush on since a long time, then what would be your reaction?
  17. Have you ever cheated with anyone?
  18. Are you someone who can lie to his partner just to safeguard yourself?
  19. Will you ever let go your self-esteem just to have an intimate relationship with someone really attractive?
  20. Have you ever played any erotic game with your ex-partner?

20 Questions to Ask a Guy about the Goals in Life

20 Questions to Ask a Guy about Motto of Life

Different people have a different set of goals in their lives. Some people are pretty serious with their motto whereas some are absolutely careless. Well! In which segment does he lie? All the 20 questions to ask a guy that have been presented here are enough to draw a sharp outline about the person.

[ Read: Deep Questions to Ask a Guy ]

  1. What is your current hobby?
  2. Have you ever tried to nurture your hobby to give it a professional look?
  3. Which hobby gives you maximum pleasure?
  4. What is your dream job?
  5. Is there any other career option that you want to look forward?
  6. Have you ever taken any bad decision in life?
  7. What is the biggest decision have you ever taken in your life?
  8. Are you doing your dream job right now?
  9. Between money and professional freedom – what would you choose?
  10. Which motivational quote do you find very inspiring?
  11. How do you motivate yourself especially when you are upset?
  12. Have you ever taken a step that could have been proven fatal to your professional life?
  13. If you are given a second chance in your life, which career path could you have chosen?
  14. What are the challenges do you face on a regular basis in your working life?
  15. Do you feel proud of telling people about your profession?
  16. What is your primary skill?
  17. In which field, do you feel you are an ace?
  18. How would you define your world – dreamy or practical?
  19. Whose advice do you take whenever you find it difficult to take a certain decision?
  20. Who helps you the most in taking life-related decisions?

All these set of 20 questions to ask a guy would give you both idea and guideline so that you strike an interesting conversation with anyone. A number of categories have been discussed here so that you never go out of topics. And, we are pretty sure that you have already filtered out the desired questions from all these.


  • These questions are just like guidelines. You can always modify your questions.
  • The best thing to do is to not judge him simply on the basis of his answers. Because the answers are simply on the basis of the questions.
  • The questions asked here are mostly closed end, but you can always make these open end as per the requirements.
  • Do not just throw random questions towards him; the main purpose is to have a discussion with him. So, you should maintain a positive vibe throughout.
  • Do not force him if he doesn’t want to answer certain questions.
  • Well! Some of his preferences might not match with yours, but that does not mean that you have to take any harsh decision against him. Sometimes, people are completely opposite but they feel amazing around each other.