engaging questions to ask a guy

Engaging Questions to Ask a Guy

Every friendship or relationship demands to know each other at least a bit. And this can come when you will interact with each other and ask questions. When you meet someone for the first time or rather initiate healthy discussion for the first time, it is essential to ask the right questions. More than guys, girls get nervous. A girl keeps thinking of the interesting questions to ask a guy when she will meet him.

But what if you are already in a relationship? Sometimes, the questions start getting repetitive, and you feel like you have run out of all of them. Be it in Whatsapp chat, or Face to face meeting, you need to keep the interaction going, and for that, something new and exciting is undoubtedly required. In that case, this article is a perfect landing spot for you.

Whether a new relation or old, Asking and Interacting is a must. Here, we have collated many groups of engaging questions to ask a guy. While we give you a head start with these questions, you can follow up with your own set once you get an answer from him.

Reasons to think of Right Questions to Ask a Guy

If this is one of your first few meets, you don’t want to scare the man away. Picking up a wrong question might become uncomfortable for the guy to answer. For example, if you like a guy and talk to him for the 1st time, and you straight away ask him about whether you both will get married or not. This becomes highly embarrassing for someone to answer.

Or rather, you indulge in his past love life or deeply personal things, he might get awkward and may never return. So, picking the right questions to ask definitely is a must if you want to take forward your meet to the 2nd outing.

And in the case of an old relation, while your man can surely avoid few wrong questions, but asking every wrong question might damage your relationship. So in order to assist you in picking up the questions to ask a guy, we have created some groups questions below. Check them out and select your desired group to explore.

List and Groups of Questions to ask a Man


Here, the questions can be enormous. Whether you are new to him or an old acquaintance, this list of questions can never get old or useless. Because if something is your hobby, you would love to talk about it again and again. And for a boy, talking about the hobby is the most engaging topic. Below is the list of some questions you can ask a guy.

#1. What are all your hobbies?

While this seems to be the most cliche question, yet important for both new and old relations. For new ones, you will get to know him more and may even find a common interest to talk to. And for old relations, a person may have found a new hobby, or you can ask him to enlist all, instead of 1 common hobby, to you. And from here, you can follow up the rest.

What all are your hobbies

#2. (If it is an indoor activity) What is your favorite part of that hobby?

Here, you will get to know what thrills him the most while he is into that activity. For example, playing an indoor sport or reading novels, a person gets excited when a particular occurrence happens in that activity.

#3. (If it is an outdoor activity) Would you mind if I accompany you in this *hobby* next time? Or, Would you take me to that activity next time?

Through this, you can observe a person’s interest in keeping the interaction long if it is a first time. Or for an old relationship, your guy would be happy to spend more time with you doing his favorite activity.

Below are some other questions to take forward. You can mold these according to the response you get from the guy.

#4. Where do you like to do your hobby the most?

#5. How long have you had this hobby?

#6. Who is your biggest idol in that sport?

#7. How often and for how long you perform that activity?

#8. Have you performed at some level?

#9. Can you make money from this hobby?

#10. Do you spend money on this hobby? How much?

#11. Do all your friends have this hobby?

#12. Do you keep this hobby in mind when you chose your friends?

#13. Do you think this hobby can turn dangerous at any point in time?

#14. Whose company do you like the most among your family and friends when you do that?

#15. What all hobbies you like to do with your family?

#16. Does your hobby interfere with your work or family life?

#17. How did you get attracted to this hobby in the first place?

#18. What all hobbies do your friends have?

#19. Is there any new hobby you wish to try?

#20. What other things excite you other than this? (Again the same set of above questions can be looked at for new activity)

Family & Friends

Family is an important part of anybody’s life. And so do friends. No matter how much you know the person, there will still be many things you don’t know about his family and close friends. So here we will help you out in choosing correct such questions to ask a man.

#1. Who all are there in your family?

#2. Where are you originally from?

#3. Have you stayed here entire life? If not, which has been your favorite stay?

#4. Whom are you most closest to in your family?

#5. If you do any mischief, who saves you?

#6. What is the most memorable thing you have done with your family?

#7. What all fun activities did your family do when you were a child?

#8. What is the funniest nickname your family has given you?

#9. What has been your favorite toys in childhood? Do you like them now also?

#10. What is your favorite childhood game?

#11. Which has been your favorite and worst subject in school?

#12. Whom do you idolize the most in your family?

#13. Which is your favorite memory from your childhood?

#14. Do your parents turn children any point in time?

#15. What is the silliest thing your family do?

#16. Do you find any of your family traditions weird?

#17. What are the superstitions you and your family believe in?

#18. Who has been your best friend in childhood? Who is know?

#19. With whom do you share each and everything of your life?

#20. Which friend you miss the most today and would like to get together again?


Here we will list some personal questions to ask a guy, but not too personal to cross any boundary. They will talk about basic nature of the guy and happenings going on around him. More than straight forward, some questions may push the guy to think deep and come up with the attached stories. You will come to know a lot of things about the person through this series of questions.

A person’s name is one of the most important things for him. So prompting him to speak about his name will definitely bring a smile on his face, and will also help you out in knowing him better. Below are some questions to help you out.

#1. What is the meaning of your name?

#2. Who kept your name?

#3. Was it a random choice or was there a reason to choose this name?

Everyone has some or the other fear in his life. And while some fears are too personal to disclose, some are funny. You can start with very light and funny reasons here, like lizard or needle. And if the guy becomes comfortable enough, you can also try delving deep into his fears. Based on his reply, you can question him more about the root cause or can even help him out in eliminating those fears.

#4. What thing creeps you out? Or, What are you afraid of the most?

#5. Has this been your fear since childhood? Has it reduced anyhow till yet?

#6. Have you done anything to eliminate it?

Opening to various exposures brings the best out of a person. Here, you can get to know his traveling choices and what kind of person he is. Also, knowing about other cultures will also be interesting for you.

#7. Do you love traveling?

#8. Which all places have you visited so far? Which one of those has been your favorite?

#9. What have you liked the most about that place?

#10. Whom do you usually travel with?

#11. Would you rather prefer traveling with family or friends?

#12. Which country’s culture do you like the most, in the entire world?

#13. Which is the last place in the world you will ever go?

#14. Which of famous monument do you hate the most?

Achievements are something a person is very proud of. They can be professional, like certificates and medals, or personal like reaching a specific aim in life. So these can make some great questions to ask a guy.

#15. Do you have any medal achievements in your life?

#16. What are your most significant personal achievements?

#17. Do you credit someone for your achievements?

#18. Which ones are you most proud of in your whole life till date?

#19. What is one thing you wish to achieve in your life which you have not done till date?

#20. What efforts are you making to achieve them?

#21. Did you ever think yourself silly while pursuing something in your life?

#22. Did you ever face restrictions when you wanted to achieve something?

#23. What is one thing that you regret the most in your life?

#24. What have one thing you done in your life that is the most satisfying even today?

A man’s nature tells you many things. How he judges things or what kind of perceptions he forms, are some of the interesting things a girl should know and observe. Here, we will list some questions that will help you find out how the guy in question is in his day to day life.

#25. What did you think of me first when you heard my name? What did you think first when you saw me?

#26. How do you find out if a person is good or bad?

#27. What qualities do you like the most in a person? And what do you hate?

#28. Given a chance to reboot yourself, what qualities would you like to add in yourself and what delete?

#29. Do you believe in astrology? What does your sun sign say about your future?

#30. Do you believe in ghosts? Do you have any personal such experience?

#31. What is the best thing you like about being a man? And what is the worst?

#32. What kind of clothes do you like the most on you or your friends?

#33. If you are given three wishes, what would you like to get?

#34. What is the silliest reason you have ever fought for?

#35. What is the most annoying thing for you?

#36. What has been the most embarrassing thing you have done in front of your crush?

#37. Which has been the funniest or weirdest experience in your life that you would want everyone to experience it at least once?

#38. Which is the best gift you have ever got? And worst?

#39. What did you want to become an adult when you were a child?

#40. When was the last time you laughed so hard that you started crying?

Below are some other set of questions. Each of these can be followed by your own set based on the answer of the guy.

#41. Did someone ever teaches you a lesson unknowingly?

#42. Who do you idolize the most in your life, and why?

#43. What has been your biggest dream in life?

What has been your biggest dream

#41. When does time run fast for you? And when slow?

#42. What is your favorite color?

#43. Which is your favorite actor from your favorite film industry?

#44. Did you ever have a bad guest experience? What was that?

#45. Is there any fact that you know and are surprised that most people don’t know?

#46. Who is the most humble and down to earth person in your life?

#47. Which is your favorite movie and TV show?

#48. Which is the very first memory you have of your life?

#49. Which social media platform you like the most and why?

#50. Which season do you like the most?


While all other questions talk about the person itself, it is better to give him a break from talking about himself. Let’s talk about some hypothetical situations here for fun and enjoyment. These can be fun for all kind of people, for those who are meeting for the 1st time or an old couple as well.

#1. How would you react if you find out vampires around you in real life?

#2. If there is an apocalypse here, how would you save yourself?

#3. If you know that the world will end in another 24 hours, how would you spend your last day?

#4. What would you do if you win 1 Million Dollars?

#5. What do you think will happen if superheroes and villains existed and they kept on fighting?

#6. Given a chance to time travel, in which period would you like to go?

#7. If you could become younger again, which memory would you relive?

#8. If you become the president or prime minister of your country, what changes will you implement immediately?

#9. If you get a robot, what would you make him do?

#10. Who are better? Animals or Humans? How?

#11. Given a chance to reborn as your favorite movie character, which character would that be?

#12. Given a chance to bring alive a movie or cartoon character, which would that be?

#13. If you get a magical wand that will take you anywhere in a fraction of second, where would you go?

#14. Imagine your wedding is to take place and you have to decide the venue and set up. How would like that to be?

#15. If the clock had 12 hours more in a day, what would you do in the extra 12 hrs each day?

General Knowledge

In this, you can talk about general news going on around you. It can be political, entertainment, sports or anything. Everyone loves to read or know about some of the other things, be it even movies. So this can form a significant component of your discussion if your interests match.

#1. Do you like the following news?

#2. What kind of articles do you like to read the most?

#3. You follow through newspaper, Television or Internet?

#4. Which newspaper (or TV Channel or internet source) you follow to stay updated?

#5. What things are going on around you upset you the most?

#6. When do you prefer going through the news?

#7. Do you take it as a necessary thing or a loved habit?

#8. Which is one thing you wish to know more?

And then on, you can talk about the latest happenings that are going on. You can ask about his views on the current happenings or can even enlighten him on something he does not know.