50 Good Questions to Ask a Guy

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At the early stages of building relationship and friendship with a guy you have crush on, you should ensure that you ask him the right questions. These questions are important because they will help learn more about his character, life, interests, future plans, temperament, and generally help develop a strong bond between the two of you. Depending on how he responds to these questions, you will be able to determine whether or not he is the right man. Here below are the questions:-

1. What makes you smile?make-you-smileIt will help you learn what makes the man happy. The answer he gives will help you learn what you should do in the future to make him smile. In other words, it will help you know him better.

2. What’s your most favorite movie?Good Questions to Ask a Guy 12The way the man answers this question will help you determine if you have similar or common interests in matters entertainment in general, and movies in particular. It will be better to date and even marry a man whom you share many interests.

3. What is that one place in the world you would like to visit at least once in your life, and why?Good Questions to Ask a Guy 2It will help you know him better. It will also help you determine his hidden interest. Does he like travelling, adventure, exploration, swimming, kate-surfing, sporting, etc.? You may be surprised to find that you dream about visiting same places.

4. What’s your favorite sport to play or watch?Good Questions to Ask a Guy 3Most guys like sports. They like talking about their favorite sport even if they don’t play it. Because it is matter that interest him, you will get the conversation flowing. If you retain some of his knowledge about sports, and if possible show interest, you may be invited to watch game at his place or somewhere else. Another important thing with asking this question is that it will let him know that you have interest in not just his likes but also his dislikes. It will let him know that you want to know more about him.

5. If I and you were dating, how would like us to celebrate our first anniversary?Good Questions to Ask a Guy 4Asking him this question will help you learn more about his interests. It will also help you establish if he values your relationship, determine his romance and whether he is caring enough.

6. Would you mind telling me some few things about your family?Good Questions to Ask a Guy 5It will help you learn more about his background. Note, sometimes you should not ask him questions he may be uncomfortable with, such as parents’ divorce matters.

7. What/where do you find most of your pride?Good Questions to Ask a Guy 6The nature of his answer will help you find more about what he considers of value to him. It could be his personality, talents or looks. Whatever answer he gives, you will be engaging him in conversation which implies that you have interest in knowing more about him. Pride is definitely a huge trait in most guys and it’s something you need to be aware of.

8. Have you cried at any movie?Good Questions to Ask a Guy 7Most guys will definitely answer no to this question.  However, if he answers yes then know that he is not weak, but that he has cute sensitive spot.

9. What is your most favorite car?Good Questions to Ask a Guy 8Many guys have interest in cars. Thus, it is highly likely that he will enjoy discussing about this topic. If he likes car, then he will let you know the car he currently drives as well as his dream car for the future.



10. What your most favorite mealGood Questions to Ask a Guy 9

It will help you know about what he would like to have for lunch, dinner or supper. It will help you know what you can prepare to make him happy.

11. What is that one thing you notice when you meet a girl?Good Questions to Ask a Guy 10

It will help you known him even better. It will also help you know who he is for real.

12. What is that one crazy thing you have done in life?Good Questions to Ask a Guy 11It will give you an insight in to his past life and also what he would like to do for fun.

13. What is your most favorite romantic activity?Good Questions to Ask a Guy 13



Men and women have different views on romance. Be careful on how you take his answer. What is of interest to you may not be so to him. Take note of how he would like to treat a person he loves.

14. What is your life’s scariest moment?Good Questions to Ask a Guy 14This will help you more about him. You will know what makes him afraid and why.

15. Who was that first girl you had crush on?Good Questions to Ask a Guy 15

It is an ice breaker that may get him laughing or blushing.

16. Who do you consider your biggest hero?Good Questions to Ask a Guy 16It will help you know what he really looks up to, and his aspirations for the future. It is another question that will help you know more about him as you prepare ground for warming to each other.

17. How do you enjoy hanging out with?

It will let you know that you have interest in him and that you would like to see him most of the times.

18. How would you define intimate? Good Questions to Ask a Guy 18This question and the way he will answer it will help you get an idea on the way your man views romance and intimacy. The answer he gives may be adorable or heart warming.

19. Would you like to cuddle with me?Good Questions to Ask a Guy 19

A good man will answer NO to this question. However, even if he says yes, it is still a good question to ask a man you have to crush on.

20. What are your hobbies?Good Questions to Ask a Guy 20

It helps you know what he likes doing during his free time. You may find that you share with him so many common interests and thus you can do some two or three hobbies together. It will help you get to know him better and exactly what he likes doing.

21. Would you like to be happy or smart?Good Questions to Ask a Guy 21

It will help you know whether he values his outward or inside appearance. If he prefers to be smart, then looks mean much to him. If he prefers happiness, then he like satisfying his inner needs.

22. Assuming your life was a movie, which part would you act?Good Questions to Ask a Guy 22

It will let you know his character. Would he wish to act as a savior, defender, or one who struggles to ensure that they attain their goal?

23. How do you handle your enemies or people you do not like?Good Questions to Ask a Guy 23It will let you know how your man views people with dissenting views, or those who do not agree with what he believes in. it is always important for a person to have liberal views towards people who hold divergent views.

24. Would you spit in the food of customer who has been rude to you?Good Questions to Ask a Guy 24Would he do something bad to a person who has wronged them? This will help you get an insight as to how your man can go to revenge against person who has wronged them.

25. Would you prefer to live in country side, city or beach?Good Questions to Ask a Guy 25Before you marry it is always important to know the likes, interest and dislikes of your man. The place where he would like to live says more a lot about his interests. If he lives on the beach then he loves coastal life. If he would like to live in the city then he likes urban life.

26. Is there possibility that I would have met you, probably in another life?

It will help you know more about his past life. If he tells you could have met in a club, then that may indicate that he used to frequent those places. There is nothing wrong in visiting clubs and other entertainment places but it will help you known how lived before you met.

27. If we had met before, how would you describe my personality?

If he says you are kind, good for you. If he says that he can’t tell at the moment then he does not want to tell you the truth, or he is still learning more about you.

28. Do you think of yourself as being nice or naughty?Good Questions to Ask a Guy 27How does the guy describe himself? Obviously, he would tell that he is nice. However, some others may jokingly tell you that they are naughty. Whatever the case, the way he describes himself says a lot about his personality.

29. What celebrity do you have most crush on?

Different celebrities are associated with different lifestyles. If he likes a celebrity figure that is respected in the society, then he is likely to get a person who values morals. If he likes celebrity personalities who have controversial life, then his life may also be controversial.

30. Whom did you give your first kiss?

The way he answers this question will let you know whether he is willing to disclose his past. If he loves you then he will not find any difficulty in telling about his past relationship including the person he first kissed.

31. What’s your best food?Good Questions to Ask a Guy 30Knowing what the guy would like to see on his table will help you known of the food that he likes most and would appreciate if you service him for birthday party, wedding day or such other big day events.

32. What’s your most favorite music genre?Good Questions to Ask a Guy 31This is a very good question that will help you know more about his likes and dislikes. If you know the kind of music genre he likes most, then you will be able to play the right tracks for him.

33. Have you ever been caught naked by somebody you respect?Good Questions to Ask a Guy 32The questions that you ask need not be on very serious matters. You can ask some humorous questions to serve as ice-breakers. If he is a person of humor then he will answer this question in a humorous way.

34. What is your most memorable childhood memory?Good Questions to Ask a Guy 33This question will help you learn more about his nature and character when he was young. His most memorable days could be days he arrived at school late, a day he recited a poem at school, a day he emerged the best in class… it could be anything.

35. What is that one thing that you did and impressed many people?Good Questions to Ask a Guy 34

This question can help you know about his achievements and deeds when he was young. For example, it could be a day he scored for his school’s team, enabling them to qualify for higher stages such as semifinals or finals. It could also be a day he represented his church or other organization.

36. Are you a morning person or night owl?Good Questions to Ask a Guy 35This question will help you know more about him. You will know if he prefers working in the night or in the early morning hours.

37. What do you fear most in life?Good Questions to Ask a Guy 36This question will again help you know more about him. For most people, their greatest fear is death. But there are other people who fear other things. Find out from your man what he fears most by asking him so.

38. What do you believe I’m thinking of you at the moment?

Ask him this question to allow him to try to imagine what is going on in your mind. It’s always good to surprise him by telling him is guess is right.

39. What nickname would you give me now based on my personality?Good Questions to Ask a Guy 38Let him try to describe who you are by asking this question. Based on how you have related and interacted so far, he will describe you in a way that may surprise you.

40. Have you ever cheated on a test in your school?

This is a good question that may help you determine his honesty. Chances are that as young boy he was caught in precarious situation by a teacher but it may not necessarily be cheating.

41. If you had just one week to live, what would you choose to do?

If you ask this question to a sharp guy, they will impress by telling you that they would like to spend the last moments of their life with you. However, even if he answers you differently, it will still suffice to let you know more about him.

42. Which animal do you love most on earth?

The way your guy answers this question can also help you know more about him. Some guys will tell you that they would be like an eagle because it soars high.

43. Which is your most favorite book?Good Questions to Ask a Guy 42The book he reads can help you know what’s of interest to him. It could be abook but inspiration, mind boggling ideas, entrepreneurship idea, history, science, or folktale among others.

44. Money or fame; what do you prefer?Good Questions to Ask a Guy 43A man can respond in any way to your question. However, whether he prefers money to fame or vice versa, the way he answers this question will help you know more about him.

45. Have you ever done something in anger only to regret later?

Asking him this question is important. In life, many people have a situation they regret of. The experience will be of help to him in future relations.

46. Asking permission or begging forgiveness – which one do you prefer?

This is a good question that will let you know more about his hidden character. It will help you know if he is submissive since he won’t find it difficult to ask for permission or beg for forgiveness when the situation demands so.

47. What are your three greatest weaknessesGood Questions to Ask a Guy 48If a man can list three of his weaknesses than he is aperson who knows more about his character and personality.

48. What are your greatest strengths?Good Questions to Ask a Guy 45

Many people are quick to cite their strengths and thus he won’t find it difficult to answer this question. Most likely he will give you several of his strengths. Take note of them and you will evaluate if at all he is honest, as the relationship goes on.

49. Are you spiritual or religious?Good Questions to Ask a Guy 46

This is a good question to ask. It will help you know more about his spiritual or religious background and know what to do or not to so as not to offend his beliefs.

50. What you want to invest in?

A good man should think of investments in the future and not just savings. Depending on the answer he gives you will be able to find out whether he thinks of investing in real estate, education, or other.

NOTE THAT these questions are just a guideline. They are not exhaustive. Depending on your relationship, some questions may not be appropriate while others may be necessary.You need not ask these questions in one day. You can ask them at different times as the situation deems necessary. Always keep in mind that building a relationship takes a lot of severance, care and understanding.

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