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50 Good Questions to Ask a Guy 

50 Good Questions to Ask a Guy

Do you have a crush on someone? Then make sure you have asked the right questions before proceeding any further. Asking questions is important as it will let you know more about the guy’s future plans, values, preferences, interest, life, background and character.

This will help you know whether you should move on to build your friendship and relationship with the guy you are interested in. We have collected 50 good questions to ask a guy. There are not just basic questions but also funny ones. They will help you dig out tons of stuffs about your guy.

So here are 50 juicy, interesting and crispy questions to ask a guy:

1.  Name that one place you really want to visit and why would you like to visit it?

This question will let you know his interests and whether he is into exploration, adventure, thrill, travelling, sporting and other things that you probably are interested. Who knows he might have dreams of going to the same places that you want to visit.

2. Let’s suppose we were to date, how would you want to spend our first date?

This is one killer digger question if you are wondering whether he would go to the next level of relationship with you. You will get to know the kind of date he wants which will in turn tell you about his romance values as well.

3. Tell me about your family and who are you closest to?

This is a good way of knowing his family background and the kind of connection he has with his family. You will know whether he values relationships but be careful and don’t get too nosy if you feel there are things he doesn’t want to talk about. Everyone has their own rifts and family matters they don’t like talking about.

4. How do you treat people who get on your nerves?

If you really want to know about his temperament, this question nails it. If you are someone who cannot deal with short tempered people, then you will get your warning right away if he happens to say things like ‘I start screaming’ or ‘I simply bang anything that is near me’.

5. If you were to describe me in detail, how would you do it?

Every girl is desperate to know what the guy they are interested in thinks about them. Even if he is a guy with a tough shell, he will say something or the other about you and you can get the hints you are looking for.

6.  What do you think about marriage in general and do you have plans of getting married?

If you are planning on getting married and you are interested in him, it is time to move on if he simply has no desire to get married or is against the notion of marriage. Things cannot be one sided when it comes to marriage.

7. Can you think of a character in a movie that you think is closest to what you are like?

Now this is probably a fun question and the best way of knowing what the guy is actually like.  This is a perfect shortcut of getting to know about his qualities, values and temperament. He could be a jolly good fellow or a sober and sophisticated gentleman.

8. Are you crazy about any kind of sport or love watching it?

Now this is a topic that every guy loves talking about because every guy is crazy about one sport or the other. Since it is a topic of his interest, you can keep your conversation going with this one. It is possible that he loves the same sport that you love and you can get a chance of watching it together.

9. What is your biggest fear?

Is your guy a real macho one? This question will help you know his softer side although most guys don’t like to admit that there are things that they actually fear as it makes the man in them look really small and petite. Let’s see if he is man enough to share his fear with you.

10. Who is your hero?

Everyone derives inspiration and motivation from someone. This will let you know who the guy adores so much and holds as a role model. This will also tell you about his values depending on who his hero is.

11. How do you like spending your free time?

This is a digger question that reveals all about his interests. You can even do some of the activities that he mentions and get a chance of spending time with each other exploring more about one another.

12. What is that one moment in your life that is frozen in your head and never melts?

This is a good way of asking about the most memorable moment of his life. You can even go on to share yours. You might be in for interesting stories and offer some of your own. It is a great ways of maintaining the flow of your conversation.

13. Would you like to share you most embarrassing moment?

He may or may not share it with you. If he shares it with you, you are in luck because it clearly shows that he feels comfortable with you. He doesn’t mind being a bit silly and has the guts to share his most embarrassing moment.

14. Have you ever cried while watching a movie?

Guys usually don’t cry while watching movies but if his answer is positive, it means you are one lucky person to find such a sensitive guy. Being sensitive doesn’t mean he is weak. It only makes him strong enough to feel more. Not every guy can do that.

15. Name that one car you really want to buy?

There is no guy on earth who doesn’t love cars. You will get your conversation flowing with this topic. He will share you dream car with you and tell you about the one he is driving right now. Girls simply love guys with hot cars, don’t they?

16. What are your favorites when it comes to food?

This question will help you prepare lunch or dinner for him or help you choose a restaurant where you can have lunch or dinner. Nothing beats cooking dinner or lunch for your guy yourself.

17. What are the first three things you notice when you meet a girl?

This will help you get to know him better and make you feel relaxed about the things he might have already noticed in you. You can even ask about those three things with respect to yourself and ask him what he thinks about those three things in you.

18. What is the funniest thing that has ever happened to you?

Every girl loves humor in a man and hates men who are too sophisticated to be true. If he is a man who doesn’t think twice before cracking jokes or sharing funny stories, what can be a better company!

19. Are you up-with-the-sun-waker or night person?

If this guy is not at all a morning person, then never think of having lunch with him. Dinner is probably the best option for the owl person. This is important information in case you want to meet him in the future.

20. If there is a customer who is really rude to you, how would you react?

This will speak enough about whether he would take revenge if somebody does something wrong to him or is he going to simply forgive and let go. If he takes revenge or is equally rude in return, then you should take some warnings here. His answer will help you dig into his personality too.

21. What will you choose between city and country side?

Knowing what your guy is interested in is important to know before marriage. It will be easier for you to make your decision if you know whether he likes urban life more or the more close to nature and peaceful country side.

22. How long did your longest relationship last?

If his relationships doesn’t last more than few months, then he is probably someone who is not so mature and is not serious about relationships. If that is so, you should probably forget about this guy because he will not be serious with you either.

23. Do you want to have kids?

If having kids is your wish and he simply doesn’t want them at all, then you should think again about the guy you are thinking about getting married. Having kids is not every guy’s cup of tea. Some don’t want them at all for the fear of taking responsibility.

24. Do you want to date me?

Did you know that even guys are really shy to answer when a woman throws such a question at them? So it is really no big deal in asking out a guy and making the first move. We are living in a twenty first century.

25. Any childhood memory that you clearly remember and never forget?

This question will take you to his childhood memories and tell you what he was like when he was young. It could be about the first time he went to school or a prank someone played on him or maybe how he secretly ate chocolates.

26. What are you biggest achievements in life?

You will get to know a trail of all the things he has been able to achieve in life and how. He will share how he achieved everything he has ever achieved and what makes him what he is today. It could about his academics or how he led his school team to the final.

27. What am I thinking right now about you?

Let him make a guess. You can see what a sharp eye and mind he has. You will know how far he is able to read your face and body language. You never know he might even guess if right. Prepare to be surprised or disappointed.

28. Have you ever cheated in any exam?

You can get to know how honest he is. Someone rightly said that one is first honest to himself and then others. If he is not honest to himself, then he may not be to you either. You should take a red alert there but don’t get too serious about it as we all have cheated some time or the other until he is a serious case of cheating.

29. What makes you laugh?

This is something really important as it will provide you with the keys to his happiness. Later on you can use this key to make him happy. If you truly want a relationship with him, then you should be looking for ways to make him happy.

30. What are the things that come in the way of complete happiness?

This question will give him a chance to speak about himself. He will share with you what actually makes him truly happy and all the obstacles and struggles that he is facing to reach there. After all, happiness is different things to different people.

31. Is there anything you want to change about me?

He might say you are flawless but he may not be honest with you. If he is downright honest, he will tell you about some of the things he wants to change about you. Remember honesty is everything in a relationship.

32. What are the ingredients of a happy and healthy relationship?

This question will you give you insight about what he thinks about an ideal relationship and what it takes to maintain a healthy relationship. This is a good question to ask a guy if you are actually interested in him and want to take the relationship to the next stage.

33. What is the best advice you have ever got about women?

Whether or not he has really received any advice about women, he can simply construct one on the basis of his experience with women. He might even tell you about his personal experiences with women and you both can share a good laugh. You can even add to his knowledge about women.

34. If you were to tell me about your worst job, which one would it be?

This is an interesting way of letting your conversation flow. He might share his experience regarding tough bosses and rude colleagues. You can drop in some of your own horrible job stories as well.

35. Suppose you get a chance of building your own house, what would it be like?

His description of the house will tell you a lot about his personality and values. For instance, if he likes it small and simple, it means he is not someone very materialistic and ostentatious. If he likes a huge house with really expensive things in it then he is probably a very materialist person.

36. If money was not much of a problem, what will your dream job be?

Everyone wants to change their most favorite hobby into profession but don’t because of money issues. He will tell you about what interests him the most and maybe you might be interested in the same thing as well.

37. Is there anything that has actually made you a strong person?

He might tell you about his struggles and the roller coaster ride his life has been. This will make you know what has really shaped him into what he is today. You might want to treat him according to what he has gone through in life.

38. What is that one thing that makes you really proud of yourself?

It could be an achievement or maybe a trait that he adores about himself. You are just giving him a chance to praise himself and may be even make up things about himself. Whatever the case, you enjoy listening to it.

39. Would you rather have exceptional intellect or unlimited good looks?

You will know whether he values outward appearance more or inner qualities like intellect. You might even get to know if he is judging you on your looks or is on the lookout for your inner qualities like your intellect and soul.

40. Do you think there is something missing in your life?

If that void in his life is linked with relationship and love, you have a good chance of assuring him that you are there to fill up that gap in his life and make him feel complete. Otherwise you can simply be his good listener.

41. Tell me about the first girl you ever had a crush on?

This question can stir in all the blushing and laughing. He will share stories of his first crush and all the silly things he might have done to gain her attention. You can go on to share stories of your first crush and keep the conversation going.

42. What would you choose between unlimited money or love?

This is yet another digger question that lets you know whether he is materialistic or prefers relationship and people. If everything in his life happens to be about money, then he wouldn’t care much about you either.

43. Tell me about you’re the most crazy moment in life?

If you want to chirp up the conversation a bit, this will do the trick. It is also a good way of sharing a good laugh. You can also go on to share some of the super crazy things that you have done and enjoy your time with him.

44. What stirs real passion in you?

Everyone is passionate about something. Is it just sports that he is passionate about or he also has passion for doing good in society and helping people around him? You will know how superficial or real he is with this question.

45. Do you have any regret in life?

He might now want to share but if he does, it means that he is comfortable with sharing stuffs with you which he normally might not share with others. That is a thumbs up for you.  you will get to know much about his conscience as well because many people don’t even have regrets when they wrong people.

46. Are you into reading books?

He may or no may not be a reader but if he is a reader you can find out a lot about him. The kind of stories or books he reads is going to tell you about the kind of person she is. The kind of characters he likes may tell you a lot about his personality.

47. Is there any artist you really adore?

If he is into paintings and art, he will probably tell you about his taste in art. In case, he is not interested in art, he might talk about a musician he likes. After all, a musician is also an artist. Someone who is not into any kind of art is probably a really dry person whose company you might not even enjoy.

48. Do you have hidden skills that only you know about?

This is a fun question that allows the guy to talk about himself and spice things up a bit too. You are giving him a chance to exaggerate and make up stories about himself just to impress you.

49. Have you become what you have always aspired to be?

Everyone aspires to be something when growing up. You can get to know all that he has always want to be or still aspire to be. This question further gives you insight into the guy you are interested in.

50. What is the best gift anyone has ever given to you?

This is a must ask question so that you know what to give him when buying a gift. You can then share the best gift that you have ever received which will help him when gifting you something.

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