21 questions to ask a guy, question game 21 questions to ask a guy, question game

Conversation and communication are important when you want to know a person, but one more important thing is what to ask. It is crucial how he thinks about his perspective and opinion towards life and different situations to know the person.

Agreed that, It takes months or even years to understand someone completely. Also, there is one who can never be understood in an entire life. But ignoring such cases, here we are sharing the top 20 interesting questions to ask a guy to learn him better.

Don’t forget that every guy has his own unique nature. So ask a fair question considering which one fits his personality—confused what to ask?

Ready to play the 21 Questions Game?

Here we are sharing the list of 21 interesting questions to ask a guy. These questions are a conversation starter. Moreover, it is a chance to get some insight into him. The 21 questions game is quite a fun way to learn about someone. But, before asking these questions, make sure you have some mutual understanding in between. Once you confirm with another person or guy’s basic nature, you are all set to go along with these funny yet informative questions.

21 Questions Game – Questions to ask a Guy

1.  What is your life purpose?

Life purpose

This is one of the best questions to ask a guy to identify their approach to life. And what is the purpose they are working on? Genuine answer to this, is enough to know how much he trusts you. Because no one shares personal goals with anyone, so easily. If they discuss it with you, then certainly you are special to him.

2.  What are the proudest things you have done so far? 

Proudest things

The answer can be anything from his sports achievement to overcoming the fear inside. But asking this question to a guy certainly feels him confident by remembering the past accomplishments.

You get to know that the hustle he’s been through and his own success stories to learn more about.

3.  According to you, What is a good relationship like?

Good relationship

Ask him this question to know, his thoughts on a relationship. That also gives you some hint to know more, if you are planning to do something special for him soon. The answer probably will be enough to understand what a relationship is meant for him. Or you may find some broken memories he has been hiding inside.

Also Read: Ways to Keep Relationship Healthy and Strong

4. What are you expecting from your future self?

Future expectation

Everyone has their own aspirations and expectations from ownself. When you ask this question to a guy if he answers without thinking a long, it means they live with a purpose. Also knows what he’s doing and where he’s going in life? Means, he’s up to something. A good question to ask, indeed.

5. What are your career goals?

Career goals

Like a personal goal, everyone has professional goals in mind to achieve and to become.

Ask a guy in 20 question game, to understand what they are doing.

Also, know his Passion. Not like an interviewer, But ask a guy this one to explain how you can help each other to achieve career goals together. Who knows you may find someone to share your passion plan with!!!

6. What will you do if you win a lottery worth a million?

Win a lottery

Ask this question to a guy and you’ll get to know more about their dreams and interest in life. 

Chances to know what priorities he has in life. You will find that Is he self-centered or the one who cares for others. See what does he prefer, personal dreams or needs of a family.

Traveling, favorite car, sports bike or anything…most guys prefer in the situation, also there is a Spider Solitaire Masters game frequently played in Europe which you can ask about. So take that as normal behavior. But if he mentions family and society in between, then he very well knows the difference between needs and desires.

Also Read: Most Important Things in Life

7. What is the weird thing you’ve done ever?

Weird thing

This can be in a list of “Weirdest questions to ask a guy”- but worth a try in any question game. As this reveals some secret of a guy, which he almost forgets but you recall those past memories again. The answer probably is a weirdest ever, but enough to bring a smile on your face.

8. Do you love what you do?

Career & job

Ask him this career-oriented question, to know whether he loves his job or not?? Or just doing it for the sake of paying bills. Normally guys don’t freely share this with anyone, without asking.

As a best friend, you want to ask him to give the moral support, he lacks.

Also, that describes a guy’s career goal and personal interest.

9. Describe yourself in one word…

Self belief

Another personality test question to ask a guy. The one-word answer is enough to read their personality and self-belief to know what he’s thinking about his own self?

Also Read: Best Ways To Find Your True Self

10. What movie you can watch on repeat?

Favorite movie

Yeah, guys love talking about their favorite movies. And can discuss the movie genre they like for hours. The question also informs you more about the guy’s interest and his free time activity. Depending on his favorite actor and movie he likes, you can plan for a movie in the future, too.

11. What is your favorite cartoon show from your childhood?

Favorite cartoon

We all have our favorite cartoon show and a character from our childhood that we liked a lot. But for a guy’s favorite cartoon is his entire childhood. Ask this question to a guy from his past and you probably give him a chance to remember those golden days.

12. What is a formula for success?

Formula for success

The personality trait question to ask a guy, knowing what they think success is made of. Basically, a simple question, but will reveal more about a guy’s values in life and views on success.

You also get to know Is he a decision-maker or just an arguer?

All given questions are a conversation starter, but this one probably starts an hourly debate. So plan in advance.

Also Read: Formula for Fortune: What Successful Entrepreneurs Can Teach Us

13. What is the dream that you just can’t get rid of?

Scariest and funniest dream

We all have scariest and funniest dream memories. But some dreams give us a thrill of a lifetime. Ask a guy about the same experiences he has been through. Every dream is a result of what we do and what’s running in our minds regularly. Be ready to hear something funny, and creative one. Another chance to know what he’s thinking about.

14. How do you spend your weekends? 


One of the best questions to ask a guy is, What does he prefer to spend his free time? The answer will be great to know how much he is desperate for weekends. Also to know his personality better this way….Find, Is he working for the weekend or living life to the fullest. The answer will be ranging from sleeping all day to do some productive stuff out of it. Also, a better option to understand his life interest.

15. What are the childhood memories you are still ashamed of? 

Childhood memories

Blast from the past. We all have those childhood memories that we just can’t get out of our minds. Because that was a scary experience from our childhood. Ask a guy about his past stories. It may seem quite fun today, But still, you can feel that terror mark on his forehead. Even don’t hesitate to share your stories, too.

16. What is the first thing you feel/do in the morning?

Morning routine

We are all habitual to our biological cycle inside us and act accordingly. Ask a guy what he first thinks when he wakes up on working days. Know Is he wakes up hurriedly or feeling excited about the work? If he’s like the second one, who sets the priorities in mind before starting a day. Then he’s a good organizer and knows managing time better.

How we think in the morning defines what we do the entire day. The question will provide you some insight into how he is serious about the work.

Before the question went off the discussion, straightway ask him what he thinks after having coffee?

Also Read: What to do Before Breakfast Every Morning?

17. Which superhero powers you wish to have?

Superhero powers

Superheroes are always an attraction for any guy. Also wishing to have that power in real life. The question, which supernatural ability he wants will definitely make him excited to answer. Something interesting to start conversion over, that guy really passionate about. Out of many superheroes characters, the selection of the one will certainly give a hint about his own character and desires.

18. What is your favorite travel destination to go on next holiday?

Favorite travel destination

An interesting question to ask a guy and to anyone. Know about his favorite travel spots and where he wants to go the next summer.

Question to know his hobbies and interests. Does he like to travel or live some free time fully??

You can get to know his interests and personality…Based on the places he picks. Adventurous personality opts for hiking & camping, whereas relaxed one prefers to chill at the beach spending time in isolation.

19. Texting and Call. What do you prefer?

Texting and call

Every guy has his own mode of communication to prefer. Ask a guy this question to understand how he likes to communicate with someone. Know what he prefers between Robotic emojis or Human voice with a feel. The question will certainly answer you on how to reach him next time.

20. What if I tell you that I have a crush on you?

Secret crush

Indeed, a bold question to ask a guy. Ask only when you have bonding with him and just to know his thoughts on the same. Especially when you know a guy from a long time and have some stories between you two, with complicated status. If you really want to know what he thinks about you, then this one is worth a try.

Also Read: Let Your Crush Know You Like Him

21. What matters more is the entry or the exit?

Pexels pixabay 235975

This question can take your conversation on the philosophical ground; everyone has different perspectives and takes on such questions. Very few people think about such details and are thinking about these things. So this question can hold a long conversation where you can share your thoughts and talk about them.

(Bonus) 21 Questions game Questions to ask a guy

The 21 questions game is the best timeless activity to do when you both are bored together. But, more than that, it is also the safest way to learn more about a guy you secretly like. Here sharing the updated list of 21 question games questions you better to ask a guy. These Bonus lists are a combining of a funny and deep question, that reveals many personal things about that guy. 

  1. Name that childhood game that, you still like to play with someone. 
  2. Cooking at home, or Dine-out?
  3. The place you like to visit very frequently. 
  4. What will your dream house look like?
  5. What is your favorite car brand? That you’re dreaming about.
  6. What are those things that make you angry, the most?
  7. Which song/movie perfectly describes your life?
  8. What will you choose: Money or happiness?
  9. What Marvel character do you wish to be like in real life?
  10. Things you are working hard to change about yourself.
  11. What is True love?
  12. If you can transform yourself into any animal, what it would be, and why?
  13. What makes the perfect life partner, according to you?
  14. Which family member are you very close to?
  15. Is there anything that you still are regretting for?
  16. Describe yourself, with just one word.
  17. Who is your role model? Name a leader you follow. 
  18. What quality or trait is so important that everyone should have it?
  19. Share the happiest moment you want to live again. 
  20. What are those things you are proud of yourself?
  21. What is your favorite television show?
  22. Are you a morning bird or night owl?
  23. What is something that you want to bring with you to your next life?
  24. Which emoji do you use frequently when you don’t know what to reply with?

21 Questions to Ask a Guy – More Ideas To Try On

21 questions to ask a guy

  1. That Spotify song you listen to for hours.
  2. Is there any secret that no one knows about you?
  3. Which website did you visit recently? 
  4. How will you rate your wardrobe management, out of 10? 
  5.  What age was the best year of your life?
  6. Have you ever thought of moving to another country and start a new life?
  7. Do you maintain a journal or routine calendar?
  8. The longest vacation you had and with whom?
  9. What are your special skills and ability that no one knows?
  10. Spending time alone or being with true friends?
  11. What makes you feel relaxed after a long working day?
  12. Which pets do you want to have at home?
  13. Have you ever done something extremely crazy thing?
  14. How can one manage their time well? How to do more in less time?
  15. Do you believe in luck or pure hard work?
  16. What’s in your new year wish list?
  17. What’s your response to a person who hurt you in the past? Forgive or Payback?
  18. Are you fascinated by brand name or buy with purpose?
  19. Describe, what makes a life good?
  20. How do you handle yourself in low moments?
  21. What is the Best and Worst thing about you?
  22. Who is the favorite celebrity you wish to hang out with this weekend? 
  23. What is your worst habit that you plan to get rid of by this year?
  24. What is your favorite social media app and why?
  25. How do you define happiness? 
  26. On about to lose an argument, what would you start doing? 
  27. Which YouTube channel or Instagram page do you follow? 
  28. What are your plans to make an awesome weekend? 
  29. Which reality show do you want to be part of and why?
  30. Which musical app do you like the most? 
  31. If you have a pet, what will be its name? 
  32. You said you prefer DC over Marvel, why?
  33. Which Korean series or movies have you just watched recently and loved it?
  34. What was your last job and why did you leave that? 
  35. How much do you enjoy working from the office than from home? 
  36. Do you hide something from your parents, what’s that? 
  37. If you want to change your name, what it would be? 
  38. What was your biggest challenge in life and how did you overcome that? 
  39. Which Disney movie is your favorite one? 
  40. Which one of us do you think will remain your friend forever?
  41. If you have a chance to be reborn again, Do you want to be human again or another animal?
  42. Which adventurous activities do you wish to try out on your next birthday?

Final thoughts: 

20 questions game or 21 questions game, pick anyone you want. But, it is actually a fun activity to perform to know someone.

Asking questions is the best way to understand someone in the first place. Showing that you want to know more about them.

If you are looking for some interesting questions to ask a guy then here presented are the best you can go along.

But before asking every single question one by one, make sure you understand his personality well. After all, you don’t want to feel him like an interrogation, isn’t it ?? Also, don’t be the one who asks always…Share your own stories in return and make it a more interesting talk.

Do you have more ideas to add to this “20 questions game” list? Then, let us know in the comment section below.

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