Good Questions to Ask a Guy – 50 Things to Ask a Guy You Like

When you have a date with a guy, we know that you will pay more attention to his look than to his personality. But, if you want to have an appropriate relationship with this guy, it will be necessary to find out more about his personality and his life.

Actually, every time you have a date you have the opportunity to find something more about the guy you like. You should keep in mind that good communication is the key of every successful relationship. If you ask your crush the right questions, you will get to know him better and you will be able to decide if he is the right person for you.

But, it is important to ask him some interesting questions. We think that every woman should ask a guy certain questions at the beginning of a relationship. There are many times when we have a lot of things in mind, but we don’t know how to ask them. If you don’t have ideas what questions to ask a guy you like, we will help you. Have you ever met a guy you like but you didn’t know what to talk to him about? If you are a shy person, it will be very difficult for you to start conversation with the guy you like.

In this article we will show you some of the most common and most interesting questions to ask a boy. Have in mind that it is very difficult to penetrate into the brain of men and to find out what they really think. But, you can try it by asking them. It is the simplest way to find out everything you want to know about the guy you like. This way you will also see if he is the right guy for you or not.

Below you will see several types of questions to ask a guy to get to know him better. These are cute questions, relationship questions, funny, flirty, random and also deep questions.

Before you ask a guy some of these questions, you should know that sometimes you may not like the answers. But, it is always better to find out the truth before you fall in love with him completely. Also, if the guy says only what you expect him to say, it means that he is not honest with you.

Just continue reading this article and you will find out what are the best questions you can ask the guy you like.

CUTE QUESTIONS

There are different cute questions you can ask the guy you like. This way you will make him talk about himself. It will be very cute to ask a guy if he has ever cried while watching a movie or to ask him to hug you. More about these questions you will see below.

  1. Did you ever cry when you were watching a movie? (Most guys have cried sometimes while watching a movie, but only a few of them will admit it. If a guy says “Yes, of course I did”, it means that he is honest and also able to show his own emotions. And it is known that sensible men are very attractive to women. Remember that crying of a man may be the sign of strength, not of weakness.)
  2. Which is the result? (This question may be the favorite one for all the guys. If you ask this question a guy while he is watching a match, he will be delighted. Also, you can ask him to explain you the rules of a game. You should have in mind that boys adore to talk about sports. They especially love when a girl is also interested in it. )
  3. What is the word that describes you most? (This is a cute question that you can ask the guy. If he tells you the word immediately, it means that he is a very self-confident and skilled guy. If it takes a long time for him to think and if he starts explaining you, then he has probably never thought about the meaning of the life and about his own personality.)
  4. What is your favorite food? (The question about the food he likes may be very cute. If you are confused and if you don’t have ideas what to ask the guy you like, then you can ask him this question. This way you will find out not only what food he prefers, but also a lot about the guy. If he says that he is a gourmet, it means that you will spend a lot of time in the kitchen if you stay with him. But, if he is eating only fish, chicken, eggs and vegetables, it means that he really cares about his health and also about his own appearance. He is probably a sport type, so balanced and healthy diet is the most important for him.)
  5. What are your favorite hobbies? (It is a great idea to ask a guy this question. This way you will find out more about his personality and his interests. Also, you will find out what he loves to do and you will see if there is something that you could do together.)
  6. What is your favorite thing from the childhood that you still enjoy? (All people would like to go back to their childhood sometimes. There must be a thing from the childhood that your crush is still enjoying. Maybe he likes building sand castles in summer or playing in the snow during the winter. You can also tell him what are the things that you miss from your childhood and what childish things you are still enjoying.)
  7. How old were you when you kissed a girl for the first time and what was it like? (This question can be very cute and it will definitely break the ice between you and the guy you like. This way you will also find out something more about him. But, you should have in mind that a guy may tell you that his first kiss was much earlier than it really was.)
  8. If you could go anywhere in this world, where it would be? (The answer to this question will tell you a lot about the guy you like. You will find out not only where he would like to live, but also what kind of weather he likes, does he prefer hot or cold weather, what kind of culture is attractive to him and many other things that may be crucial. After the answer you get, you will be able to see if you could live with him in the future. )
  9. Can you see that you are making me smile all the time? (Every guy would like to know that he is the reason for the girl’s smile and happiness. After you ask him this question, he will certainly try to make you even happier. If he really makes you smile all the time, you should think about having a more serious relationship with him. One of the most important things of any relationship is that you are feeling satisfied and happy, so the guy who makes you smiling all the time may be the right for you. Think about that.
  10. Do you want to hug me now? (This is the cutest thing you can ask the guy you like. If his answer is yes, he also likes you and you can start cuddling each other.)

FLIRTY QUESTIONS

Now we will see something more about the flirty questions that you can ask the guy you like. Flirty questions can be very important at the beginning of a love relationship.  Although before flirty questions were only for the guys to ask the girls, nowadays most women are ready to ask guys some flirty questions. If you don’t have any ideas what flirty questions you could ask the guy you like, we will help you.

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  1. Would you like to go out with me more often? (This is a question in which you are directly telling your crush that you are interested in him and that you would like to see him more often. If he says yes, it means that he really likes you, so you don’t have to worry. In this case he will be already planning your next meeting and the activity you will do together.

But, if your crush says that he would like to see you more often, but he doesn’t have too much free time, it means that there are many other things that are more important to him than you. He probably likes you, but not enough. This question will help you know if there is a chance for some more serious relationship or not. If it is enough for him to see you once in a week or once in two weeks (and you both live in the same town!), then you should look for some other guy that will have more time for you.)

  1. What do you notice first when you meet a new girl? (This question is a typical flirty question that will help you know what kind of girls your crush likes and what the most important thing for him is. If he says that the physical appearance is the most important, if he looks at a girl’s ass first, then you should think well before you decide to be with him. It means that he will leave you as soon as other more attractive girl appears. And that’s not what you want. Of course, physical appearance is important for any relationship, but if it is the most important for him, then he may not be a guy you are looking for.

But, if he says that the first thing he has noticed were your eyes or your beautiful hands, it can be interesting. If he has noticed your smile and your voice first, it can mean that he could see in you something more than your external beauty.

Unfortunately, there are many guys who will not give you an honest answer to this question. Your crush may tell you something you want to hear even though it may not be the truth. Because of that, you should watch carefully his reaction and you will get the right answer.)

  1. What is your favorite romantic activity that you would like to do with a girl on a date? (If you decide to ask this question the guy you like, you should have in mind that men and women have a different perception of romance. Even though you would like to go out with him and to have fun, he may prefer staying in and watching some movies together. )
  2. What workout are you doing to have such a beautiful body? (Every guy would like to hear this question from a girl he likes. Not only will you show him that you have noticed his great body, but you will also find out more about him as a person. So, don’t wait anymore and ask your crush this flirty question. Remember that every guy loves to be complemented and he never gets tired of it.)
  3. How is it possible that someone like you is still single? (If you ask a guy this question, it will be obvious that you like him and that you think he is perfect. Also, this way you will boost the self-confidence of the guy and he may realize that he wants to begin his new dating career with you.)
  4. Is your brother as good looking as you? (The questions about his good looks are always a good option and you can never go wrong with them. As we have already said, every guy loves to be complimented. This question will boost his self-confidence and he will be even more interested in you.)
  5. Did you ever try online dating? (Online dating can be interesting, but not every guy would admit that he has tried it. Your crush may be afraid to admit that, but you can relax him by telling him about your online dating experiences. Most young people have tried online dating, so you don’t have to worry if his answer is yes. He is only a guy who believes in love and who maybe didn’t have enough luck to find the right girl for him in real life.)

DEEP QUESTIONS

If you want to test your intellectual compatibility with the guy you like, you should ask him some deep questions. This way you will see what stimulates him and you will learn more about his views on some controversial topics. If you don’t have any ideas, read carefully this article and we will show you which deep questions you can ask the guy.

  1. Do you believe in real love? (This simple question can tell you a lot of things about the guy himself and also about his own views and opinions. You should know that there are persons who believe in real love and others who don’t believe in it anymore.

The guy who has suffered too much because of love, probably has lost his fate in love. It is usually a type of a guy who had a long relationship and his girlfriend has cheated and betrayed him. If you are ready to accept this and to return his fate in love, this answer will not be a problem for you.

Of course, it would be much better to hear that your boyfriend already believes in love, even though his past love life has been difficult. But, if your crush says that he is not able to love a girl again, you should go away from him as soon as possible. It means that he will never give you the love you deserve.)

  1. Do you believe in God? (It would be nice to know if your crush is religious or not. The best option would be if you both had the same opinions about God and religion. If he believes in God, he will certainly appreciate your question and he will want to talk about that more thoroughly.)
  2. Would you rather have love or money? (If you are looking for the truths to ask guys, this question can be the right choice, even though it may be quite difficult. Every girl would like to hear that her boyfriend prefers love, but it is not always the truth. If your crush says that he would rather have money than love, you may be disappointed. But, we recommend you to listen to his opinion about that and his justification. You also know that money is important, so don’t judge him immediately. Of course, it would be best to have both love and money.)
  3. Is it more important for you to love or to be loved? (This is very important and meaningful question. Your crush may not give you the answer immediately. He will probably think a little before he answers you. You should have in mind that everyone has a different opinion about this question, so you don’t have to judge your crush, whatever he says. Then you should also think what is more important for you.)
  4. What is worse for you, failing or never trying? (This is a very deep and thought-provoking question and the guy will certainly like it. If he answers that failing is worse, it means that he will never be brave enough to do certain things in his life. He will always be afraid to risk and to try something. You should think well if you would like to live with such man.)
  5. Would you break the law if it was necessary in order to save a loved person? (This is a very deep and extremely difficult question that will make your boyfriend think about that for a while. We are sure that it would be also difficult for you to decide what you would do in this situation. If he says that he would break the law in order to save a loved person, it means that he would do anything for love. Maybe he is the man you really need. )
  6. What do you think, are you a happy person? (This question may look simple, but it is not. It could be one of the most difficult questions ever. Being happy is a relative term. If the guy says that he is a happy man, it means that he is satisfied with himself and his own life. It also means that he is grateful for all the things he has in his life and that little things make him happy. But, if your crush says that he is not a happy person, it means that he probably has negative views on life and that he is pessimistic. Think well if you need such a negative person in your life. )
  7. What is the biggest doubt that you have? (This question can make him thinking a while. You should have in mind that all people have doubts. We can have doubts about ourselves but also about the world around us. If the guy shares his doubts with you, it could create a strong bond between you two.)
  8. What thing would you not do even for 10 million dollars? (This can be a deep but also a funny question that can tell you a lot about the guy. This way you will find out more about him and his personal opinions and morals. You will also find out which are the activities that he hates. For example, he would never be with other guy, even if someone gave him 10 million dollars.)
  9. What are you most proud of in your life? (This question will also make a guy talk more about himself and also about his life. You will also find out what kind of person he actually is and what is really important to him.)

FUNNY QUESTIONS

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As we have already said, it is important to ask your crush some serious and deep questions. But, these questions could be a little straining, so it is recommended to mix them with some funny questions. This way the atmosphere will be relaxed and comfortable and the conversation will keep going. It is always good to ask your crush funny questions that will make him smile and talk more about himself.

These questions will also make the guy feel comfortable in your company. There are a lot of funny questions that you could ask a guy, so below you will see some of them.

  1. What is the craziest thing you have ever done in your life? (This question can be funny and it will help you find out more about the guy and his past. This way you will know how far he is ready to go in his life and you will decide whether you need more excitement or it is enough for you.)
  2. What would you do if you won a lot of money in the lottery? (If you ask your crush this question, you will find out what are his financial priorities. It is very important to know if he would spend all his money in a few days or he will save it for some more important things. You will also know if he lives from one day to another or he has some long-term plans. It is very important for you to know that, especially if you also look to do future more seriously. If he tells you that he will spend all the money on material things, it means that he is honest, but a little shallow.)
  3. What makes you smile? (This is one of funny questions and it will certainly make your crush smile immediately. Then he will tell you what things in life can make him smile. If you can do some of these things to make him smile, then you should try to do them more often. This way you will make him happy and he will realize that you are the right woman for him.)
  4. Who is your celebrity crush? (This question can be quite interesting. This way you will know who his ideal type of woman is and what kind of women he likes. Also, you will know if you are his type of woman.)
  5. If you wake up in the middle of the night, what would be the scariest sound you could hear? (If you ask the guy this question, you will find out what he is afraid of. He will probably talk about his other fears or he may want to make a joke about this question.)
  6. What is your favorite character from the childhood? (The guy will like this question and you will certainly like to hear that his favorite character was Spiderman or Superman. Every woman would like to have a superhero in her life.)

RELATIONSHIP QUESTIONS

Of course, it is important to ask your crush some questions about the relationship. What is the most important for him in a relationship? What qualities his girlfriend should have? How would he celebrate his first anniversary with a girl? Would he like to have children? These are only some of the relationship questions that you could ask the guy you like.

If you are already in a relationship, these questions will make your relationship much better and stronger. Now you will see something more about these questions.

  1. What qualities your girlfriend must have? (This question may be vital for your relationship. You will also see what drives him crazy. This way you will see whether you could be his potential partner. If you own the qualities that he is searching for in his partner, then it is a good sign. You may be the right woman for him. But, if he is searching for the qualities that you don’t have, then you should think well if you will see him again. Maybe you are just losing your time with this guy.)
  2. Who is more important for you, your girlfriend or your friends? (It would not be bad to ask your boyfriend this question but don’t do it directly and unexpectedly. There is no guy who will leave his friends because of his girlfriend. Of course, you should not ask him that! It would be nice to know how important his friends are to him, because you don’t need a boyfriend who will value his friends more than you. But, you should also have in mind that it is not good to have a boyfriend who doesn’t have friends at all.)
  3. What are your expectations in a love relationship? (It is good to ask a guy this question, because each person has a different opinion about relationships. It is best to know at the beginning what he expects from you and also if you are ready to behave like he wants. You will see much clearly if you are one for another.)
  4. Would you like to have children one day? (This question is very important if you would like to have a more serious relationship with this guy. Of course, you should not ask him this on the first date, but later in the conversation you can include this question, too. Try not to be so serious when you ask him that. You can take it as a fun question, but you will get a very important answer. It is better to know it earlier than to realize after a couple of years that your partner doesn’t want to be a parent.)
  5. If we were in a relationship for one year, what would we do to celebrate our first anniversary? (If you ask a guy this question, you will immediately get to know him much better. You will see if he is romantic or not and how would your relationship be like after one year. You would not like to hear that he doesn’t love anniversaries and other dates that are important to you.)
  6. Are women equal to men? (This is one of the serious relationship questions that you could ask the guy you like. The answer you would probably love to hear is yes. It is better to know this at the beginning of a relationship, in order to prevent problems later in marriage. Maybe he is a type of a man who expects that woman works everything in a house or he is a typical chauvinist and he may want to be a boss in a relationship. Because of that, it is best to ask him this question and to be sure that he thinks women are equal to men.)

RANDOM QUESTIONS

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Now you will see some of the most interesting random questions to ask a guy you like. This way you will find out something more about his favorite books, animals, but also about his family. You can also ask him about his regrets and about the most awesome moments in his life.

  1. What is your favorite animal? (With this question not only will you find out what is a favorite animal of your crush, but you will also find out something more about his own personality. If he likes dogs, he must be a good person and you will probably like him. If he likes cats, he must be a sensitive and caring person. If his favorite animal is lion, your crush may be very outgoing. Think well and decide if you like the personality of your crush.)
  2. What is your favorite book? (This can also be an interesting question that will help you get to know the guy much better. If you love reading books, then you probably cannot imagine being with a person who doesn’t read books. But, if your crush also loves book, that is great. Ask him what his favorite authors and books are. You can also discuss about your favorite book genres, so you can recommend him the book that you have recently read.)
  3. What is the job of your dreams? (If you ask your crush this question, you will find out something more about his goals in life and also about his dreams. If he tells you immediately what he would like to do in the future, it means that he has thought about this before. He is probably an ambitious and responsible young man who is planning his own future. But, if he doesn’t know what to say, it means that he may not be the right man for you. Who would like to be with a person who doesn’t have dreams?)
  4. What is your favorite song? (This is a random question that will also determine your compatibility. If you like the same genre of music, it is great and you will get on very well together. However, if the guy loves different music genre, it may not be the problem. You could ask him to play his favorite song and maybe you will also like it.)
  5. When you go on a first date with a girl you like, would you ever let her pay the bill? (This question can tell you a lot about the guy. If he says that he would let her pay the bill, it means that he is not the gentleman enough. Think about that before you go to a next date with him. Maybe he will expect you to pay the bill.)
  6. Do you have any regrets in your life? (If you ask the guy this question, you will find out more about his past and also what are the worst mistakes in his life. He may tell you some interesting or even embarrassing situations from his past. Also, you may find out more about the things that your crush wanted to do but he didn’t. If you are curious, the answer to this question may be interesting for you.)
  7. What was the most awesome moment in your life? (This question will be a great way to get your crush talking. The guy will certainly like to tell you a good story and you will find out more about the things that are important to him. Every guy loves to talk about awesome moments in his life, so if he notices that you are listening to him carefully, he will be very happy.)
  8. What is the movie that you can watch over and over again and you never get bored? (Your crush will certainly like to talk about his favorite movie. This way you will find out what type of movies he prefers. If you also like watching movies, you can suggest him watching his favorite movie together. He will be certainly delighted and this will help you get closer to him.)
  9. What are your personal and professional goals? (This is one of the questions that you have to ask the guy you like. This way you will find out more about his ambitions, his opinions and his future plans. Of course, you will also see if you are included in his personal goals. Also, you will find out how much time he spends at his work and if he has any plans to move for a career.)
  10. Who are your family and your friends? (At the beginning of a relationship it would be nice to find out something more about his family and friends, too. How old are they? Where do they work? What are their mutual relations? All these are questions that you could ask the guy about his family and friends.)
  11. Where would you like to move? (If you ask a guy this question, you will get to know him much better. He may tell you that he would like to live in a big city or he prefers a small house in the village. This question will also tell you if the guy prefers night life and crowded streets or he is a man who would like to have a garden, pets and, of course, children.)

Now you have seen 50 questions that can make your date funny and even unforgettable. But, keep in mind that you should not bombard a guy with all 50 questions at once, because in this case he will certainly run away as soon as possible.


If your conversation is good, you should not interrupt it and ask the guy these questions. If there is a silence in a conversation, that’s a great opportunity to ask your crush these questions. You should choose the questions that you really want to ask and also the questions that are suitable in a certain situation. You should keep in mind that every guy is different, so it is recommended to choose the questions that will work best for the guy you like.

Also, we recommend you to ask a lot of follow up questions. This way you will find out more about the guy you like and you will also keep the conversation going on.

The purpose of all these questions is not only to find out something more about the guy, but also to show him that you are interested in him and his life. You should also keep in mind that guys like when a girl is listening to them carefully and when she is interested in what they are talking.

If you are very shy to ask him something, it is not good, because the guy may think that you are not interested enough. Remember that it is very important to show your interest for him and you can do it by simply asking him any of the questions that we have suggested to you. If you are too shy, you can use these questions to ask a guy over text.

Also, you should keep in mind that guys enjoy answering interesting questions and the only thing you should do is to ask them and to listen to them carefully. A very important thing is that these questions will not offend the guy, but they will only help you start and keep the conversation going. Have in mind that guys don’t get offended easily like girls, so you can go ahead and ask the guy some extra personal questions that will help you get to know him much better.

We hope this article has been interesting and also useful for you. We hope you have more ideas and you know what to ask a guy. You have seen some of the most common cute questions, flirty, deep, random and other types of questions. We hope you will choose the questions that you are really interested in. You should know at least 20 questions to ask a guy at any moment, in order to avoid any uncomfortable silence during the conversation.

As we have already said, good communication is the key of every relationship and you should always keep it in mind. Don’t wait anymore and ask your crush some of the questions that you have seen in this article. After you get the answers, it will be much easier for you to decide what kind of relationship you would like to have with this guy.

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