Home Love & Relationship 40 Personal Questions to Ask a Guy

40 Personal Questions to Ask a Guy


When it comes to getting to know a guy, it’s definitely not an easy task. Guys are very guarded of who they are and their feelings. This makes it extremely difficult for them to come out and tell you about who they are and what they want in life.

Luckily, there are ways to get them to spill their deepest desires. All you really have to do is ask. If you ask the right questions, you’ll get just the answers you’re looking for. Here are 40 personal question to ask a guy if you want to get to know them on a deeper level.


  1. What’s the first thing you’d do with a million dollars?

This is a perfect question for being able to tell if he’s a selfish person or not. Will he buy himself a new car or would he give some money to a charity before helping himself to the funds? Finding this out can help you discover what kind of person he is.


  1. What’s the most embarrassing thing you’ve ever done?

This is going to be not only a really funny conversation, but you’ll learn a lot about what will embarrass this guy. Maybe he’s not easily embarrassed but then maybe he is. This can help you with how to act around him in different situations.


  1. What’s the meanest thing you’ve ever done?

Some people can be really brutal and mean and finding out if this guy is that way will come in handy. Asking this question may be difficult for them because nobody wants to admit to being mean, but it’s necessary for you to know.


  1. What’s the worst lie you’ve ever told someone?

This is the best way to find out how great or bad of a liar this guy is. If you ask this question and they have a really mild lie, it’s safe to say they’re not a big liar and you won’t have to worry too much about them lying around you.


  1. Would you ever give up a night with the guys in order to take care of a sick girlfriend?

This is such an important question because it shows you his priorities. It forces him to basically tell you if he would ever give up a night with the guys in order to take care of you. This also shows his maturity and whether or not he is really ready to be in a relationship and deal with all those responsibilities.


  1. What’s the most dangerous thing you’ve ever done?

Finding out what someone considers is dangerous can tell you a lot about their courage and bravery. So make sure to ask this question if you want to know just how daring someone really is. This can also help you decide how fun they’ll be and if you’re truly compatible that way.


  1. What would you do if your ex girlfriend tried getting back with you?

Not only is this something we all wonder, but it’s super important to know whether or not a guy is completely over their ex. If he hesitates and doesn’t know what to say, chances are he’s still thinking about her and they’re not truly over. Be careful when asking this question, though.


  1. Who is the most important person in your life?

If you really want to know how close this guy is with his friends or family, this question is always really important. Finding out who is the most important to him will help you understand their priorities and what they truly find important when it comes to relationships.


  1. Who was your biggest hero growing up?

Whether it’s superman or their dad, this question can tell you a lot about who they are now. If they always looked up to their dad and you know he’s a hardworking, great person, you can expect that this guy will want to grow into a man like him – which can tell you just how great he really will be.


  1. What do you think of an open relationship?

Open relationships can be touchy subjects, but it’s important to establish a baseline on how serious this guy is about a relationship. Is he okay with dating other people while with someone else or is he strictly a one woman kind of guy?


  1. Who is your worst enemy and why?

If this person has to distinguish between multiple people who are his “enemies”, they’re probably not a very good person. However, if he can’t think of someone who he hates enough to consider an enemy or who hates him enough, then it’s safe to assume he’s a relatively great guy.


  1. What’s something that stresses you out the most?

People have very different things that are stressful to them. Someone could find social settings stressful while others find schoolwork and chores to be stressful. Determining what stresses him out can help you when it comes to helping him during a stressful time.


  1. What makes you feel really overwhelmed?

Just like stress, people get overwhelmed about different things. Knowing what sets him off is going to help you understand him better and know when you help and when to back off and let him deal with things. This is another way to get a sneak peek at his true feelings.


  1. What are you most attracted to in a girl?

If you’re brave enough to ask this question, then get it out there. Knowing what he finds most attractive in a girl can help you understand what it is he’s truly looking for. That can help you determine if you are even the right girl for him in the first place.

  1. Have you ever helped a homeless person in need?

Helping the homeless is a pretty controversial issues some people face. On one hand, you’re enabling them to continue to beg for handouts and on the other, you’re bettering their hard life. Find out which way he sees it and if you’re compatible when it comes to that topic.


  1. What are your dating deal breakers?

Everyone has those few things that would completely be a deal breaker in a relationship. Knowing what his are can help you know if you have any of them. People usually don’t come right out and say what they would consider a deal breaker so asking is a must.


  1. What’s the most adventurous thing you’ve ever done?

Some people think going camping is adventurous while others think that’s not adventurous at all. Knowing which category they fall under can help you see if you two think the same things are adventurous or even if he would add some adventure into your life.


  1. If you could be one other person in life, who would it be?

Some people will say they don’t want to be anyone else and others will have a list of people at the ready. This determines how happy someone is with who they are. It’ll help you understand his insecurities and how he feels about himself.


  1. What would you change about yourself if you could?

This is something else that can help you understand their insecurities. He may say nothing and he may also have a long list ready for you to hear. Knowing these can also help you with how you compliment him and make him feel good about himself.


  1. What was the most awkward situation you’ve ever been in?

I think we’ve all been in some really weird situations, but some people would consider different things to be awkward or uncomfortable. Knowing just where the guy you’re talking to draws the line will make conversing with him so much easier.


  1. What was your favorite holiday growing up?

I think we all have that one holiday that stands out in our minds from childhood. Knowing which it is can help you understand them a little better by knowing what type of holiday or situation makes them the happiest and what they value most.


  1. What makes you really sad when you think about it?

There are always a few things that people can’t really think about without getting a little upset or even really sad. By asking this question, you’re learning a lot about how this guy feels about certain subjects and that will help you maneuver the conversation depending on the mood.


  1. What are you happiest with in your life right now?

Knowing how happy someone is in a certain part of their life can help you understand just where they place their priorities. If his job is going well for him, you know he’s someone who puts work above most other things in his life.


  1. Where is the one place you go to when you want to be alone?

Everyone has that one little place where they can escape to if they want to be alone. Knowing just where that is can help you understand what type of mood they are in whenever they go to that one place no matter if it’s their bedroom or a secret getaway deep in the forest.


  1. Would you rather spend your day at a history museum, an art show, or a science museum?

Knowing which type of interest they have is going to help you know them a little better. If someone is more interested in art than science, it shows that they’re more emotional that other people and if they prefer history over all, it shows they value what has been.


  1. What is your all-time favorite movie?

Movies tell us a lot about someone’s deepest desires. If they love an action movie, they’re probably a much more adventurous person than those who enjoy dramatic romances. Learning their favorite movie can help you truly understand them.


  1. What’s a controversial topic that makes you the most angry?

There are so many different controversial things going on in the world today and knowing which makes him the most angry can help you identify what his passion is. It also helps you know which topics to steer clear of during a conversation.


  1. What’s the one thing that can always calm you down?

It can be a song, a certain food, or even a good movie they really enjoy. No matter what it is, there is something that has the ability to calm someone down and knowing it can help you understand how he processes his anger or pain.

  1. What is your biggets turn off?

I’m sure you’re thinking about certain turn offs for yourself right now. Everyone has them. By knowing what they dislike the most, you’ll be able to avoid those things in order to make him like you a little bit more than if you ended up doing something that he hates.


  1. Are you terrified of anything in particular?

Spiders, ghosts, snakes, everyone has something they’re scared of. If it’s superficial like a spider, it means he probably doesn’t think too deeply about bigger issues. If it’s something more profound like dying, he probably thinks about life’s bigger issues more.


  1. What is your deepest desire in life?

Everyone should know a person’s deepest desire if they really want to know about them. Some people don’t have much to desire because they’re happy with the life they have but others have a huge list of what they want out of life and knowing what it is helps you know them.


  1. What’s your biggest insecurity?

This is ultimately to see just how insecure a person is. If it’s something so big as they hate their face, that’s usually cause for concern because it usually means the jealous type. But if they’re pretty happy with who they are, it’s safe to say they won’t be too jealous about much.


  1. Is there a topic you absolutely refuse to talk about?

Some people just have certain subjects they won’t talk about due to certain things in their lives and that’s just find. Knowing what this is can help you to avoid topics that will trigger an upset or even an angry response.


  1. Have you ever been in love?

This is a really important question to ask because it can tell you a lot about someone and their actions. If they never have been, it’ll be easier to tell when they do fall in love. But if they haven’t, you may have to be cautious about certain things because they may be hurt or upset about them still.


  1. If you died tomorrow, what would you be most proud of in your life?

This can tell you a lot about what someone finds pride in. Make sure to ask him just what he would be proudest of in his life so far and you’ll be able to understand what he values most in life. This will be sure to help you know what his life will be focused on when he’s older, too.


  1. Do you prefer to be in a big group or just with a few people?

There really are two different types of people. Knowing whether or not he thrives in a large group or in a smaller group can help you understand his level of attention. He may need a lot if he prefers larger groups and he may not need much at all if he likes to be in smaller groups.


  1. What’s the worst date you’ve ever been on?

This is a lighter question that will most likely result in some laughter, but it’s also fun to hear what someone finds to be a bad date. It’s also a fun way for you to get him to open up about his previous relationships and dating life in general.


  1. What’s most important to you about religion?

Some people aren’t always religious, but it’s important to know if the two of you are on the same page in a relationship. So make sure to ask this question in order to understand just how religious he is or even if he doesn’t think religion is even important at all.


  1. What is a weird habit only you have?

This is another way to just get to know the habits or quirks of a guy you like. Everyone has little things about them that are very weird and unique to them. It’ll help you to understand certain things about them and just to laugh at the weirdness and individuality that he has.


  1. Would you rather be really rich and unhappy or happy with not very much money at all?

This is the ultimate question to ask to know what’s more important to someone. You never know if someone values money over happiness and knowing which can help you determine if they’re really someone you like.

Getting to know a guy can be really hard work since they’re usually so closed off. These questions will definitely help you get to know him better and on a deeper level.


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