40 Personal Questions to Ask A Guy


At times, it can be difficult to figure out the type of questions that you should ask your significant half.  This is despite the fact asking questions can be a good way of knowing more about him. The good news is that you can use our handy list to find some truth about him.

Personal Questions to Ask A Guy

  1. Who is your best friend?

This is a good question to start with as it will allow you to discuss an issue that he is comfortable with. The answer you get will tell you a lot about him. For instance, if his best friend is a childhood friend, it is an indication that he values loyalty.

  1. What are you phobias if you have any?

This is a nice question to let you get personal without looking as if you are trying to interrogate him.

  1. I love your outfit. Where did you buy it?

There are high chances that your man knows that you understand where he does his shopping. But the fact that you love his outfit will leave him pleased.

  1. Which is your favorite vacation destination?

This is a question that many people love discussing. Your man will be glad to talk about his holiday which was a blast in another country. As he talks about his experience, you will have an idea of his perfect getaway.

  1. If you had the opportunity to be a girl, would you accept it?

This is a personal question that will display your funny side.  If he tells you yes or even no, find out why.

  1. Who do you love most in your family and why?

When you ask about this question, you will have an opportunity to learn more about his family members.

  1. Who was your first love?

It can be fun to know when your man loved for the first time and who he said these words to. This many end up surprising you.

  1. Do you believe in God?

This is a good opportunity to know whether your partner is a religious person. This will give you insight on whether you are likely to match in matters of faith.

  1. Can you forgive cheating?

This question is not supposed to live you a ticket to c heat but it can offer you some important insight into how he takes the matter of infidelity.

  1. What is your feeling towards your exes?

Your aim is not to begin a fight but to get an insight of his attitude towards relationship.

  1. Which book did you read and felt that it changed your life?

Literature definitely affects the reader in a profound way. Find out the book that transformed his life and how it did that.

  1. Do you love to talk dirty online or on the phone?

Again this can be fun to hear and you may have an idea on what turns him on.

  1. Which is your most embarrassing moment?

Do you want to get an opportunity to laugh at him? Ask him this question and you will have an opportunity to laugh your heart out.

  1. Which is the greatest lie that you ever told to your parents?

This is a good question to understand part of his childhood. You can follow up on the question by finding out whether he was caught and how it happened.

  1. If you got an opportunity to star in a movie, which one would it be?

This question can help you get a glimpse into his fantasy.

  1. Which was your happiest day?

The answer could be an afternoon that was spent in a zoo or even a picnic that he went as a teenager. In case he had a sad upbringing; he can talk of the moment when he passed his math exam.

  1. What is your idea of having fun?

This is a good question particularly if you are just learning about him. Finding out what he does during his leisure time can offer you a glimpse into his hobbies.

  1. Do you like having total privacy?

This can offer you a glimpse into his personal life. You can follow up the question with the things that he does when he is alone.

  1. If a song was to talk about your life, what song would it be?

This question will serve two purposes. It will offer you a glimpse into his personal life and you also get to learn about his favorite musician.

  1. What five things do you think you need to achieve before you turn thirty/forty/fifty?

This is a good question to help you learn about his dream and ambitions. This can offer some important discussions even though you need to be careful on matters of finances and kids.

  1. Where do you see yourself in 10 years in your career?

Again this is a good question to help you find out whether you are dating an ambitious person. Even though he may feel as if he is being interviewed in a job, you will get an opportunity to learn about his professional ambitions.

  1. When you get very angry, what do you do to minimize the anger?

While this question allows you to venture into something serious, it is a good opportunity to know the kind of person you are dating.

  1. How was your previous relationship and what caused the breakup?

We all love to know about the past relationships of the people we are dating. If you are already comfortable with someone, it is time to find out about his love history. Ask him to explain what ended the relationship. This will help you find out whether he is a victim of a cheater or he is the jealous and controlling type.

  1. If you had an opportunity to correct your past, what would that be?

Use this question to find out if he has a bad history and if that history is something that you can put up with.

  1. Which is your strangest habit?

This is another question that can help you to mind out about his dark side.  This is important especially for the purpose of doing background check on him.

  1. How would your rank your sex appeal?

This question can allow you to get naughty without necessary looking as if you are craving for his attention.

  1. Do you love showing romance in public?

This is a bit personal even though it is not annoying. The question allows you to get an idea of the kind of person he is whether reserved or an attention seeker.

  1. What is the yuckiest thing that you ever did?

This question can give you an opportunity to inject humor into your conversation. You will also get an opportunity to have a glimpse into his naughty side.

  1. Do you think one-night stand is okay/bad?

You can use this question to learn about his general views on sexuality. He may be easy and free or may be more interested in a monogamous relationship.

  1. Which question would you never answer?

Before you ask this question, you should be prepared not to push him for an answer later. However, the question will let you know the areas that he is not comfortable discussing.

  1. What are your biggest fears?

No matter how confident a man may be, he definitely has his fears. When you are aware of his insecurity you will get to know what you can do to ensure that he feels great about himself.

  1. What is your idea of a perfect relationship?

This is a good question to test what he expects of you in the relationship and how much he is ready to offer. This will give you an idea whether he is the right person for you or whether you are the perfect match for the kind of woman he is looking for.

  1. Have you ever planned a surprise party?

This question will give you an idea of how romantic he can be. Follow the question by asking him whose party it was. However, you should not be surprised if he tells you that the party was for the ex.

  1. How would you handle a situation where you ex ask you to get back together again?

This question will help you know whether he is committed to the relationship. If he says that he would get back to her, then it is time for you to run. However, if he says that he would reject, it shows that he has gotten over the relationship and he is ready for you. If he says that he would tell her that he is seeing you that would add some extra points.

  1. What’s the most risky thin you have ever done?

There are some guys who like playing safe and will think that ice skating is for people who do not love their lives. The answer you will get to this question will help you understand whether he is an adventurous person or not.

  1. How many ladies have you dated before?

The question can help you get a lot of details concerning your man. However, you must understand that very few men will tell the truth concerning this question. When he gives a number that is low, it is an indication that he needs a serious relationship. When he gives you a high number, it is an indication that he is a player who loves sleeping around.

  1. Do you have a dream tattoo and what is it?

You may want to find out whether he is a tattoo person. If he is, the kind of tattoo that he loves will show you what his interest and what he loves.  He may want a tattoo with an image of his mother or it could be of his favorite musician. Whatever way, it is an indication of where his heart is.

  1. Have you ever cheated?

In case the man tells you yes, it is advisable to end the relationship there. If he did it once, there are high chances that he will do it again. However, you need to appreciate the honest answer he gives you.

  1. What would you consider to be a deal breaker?

This is an important question that you should not forget to ask. For instance, he can answer that his deal breaker is a girl who will not give him a blowjob and you absolutely hate that, this is an indication that the relationship won’t go far. Therefore, you will need to let him know your stand the earliest possible,

  1. How financially stable are you?

Definitely you aren’t seeing him because he has money or doesn’t have. However it is important to know if your man wants a lady who will stick by him as he struggles through college.