150 Deep Questions to Ask a Guy – To Know Him Even Better

Questions to ask a guy

We have created a list of the most wanted deep questions to ask a guy. These are not just some random questions. These questions to ask a guy are designed specifically to trigger his mind. Handsome guys are not easy to talk to. You can start a conversation with any guy you want; all you need is the right questions to get started.

We compiled some of the best questions to ask a guy. Experts from our team designed these questions in a way that they look easy but are very much deep inside. You will know a lot about that guy from his answers on those questions.

List of Deep questions to ask a Guy:

These questions have a bit of commentary to give you a direction about the question. You can skip the commentary and can make your sense of questions. So, here are some of the best questions to ask a guy.

Question 1: Do you play video games? Which game is your favorite?

Guy playing a video game on Deep questions to ask a guy
Guy playing a video game on Deep Questions to ask a guy

Yes, there is a 99% chance that it is played a video game and must love some of those games. Guys love to play video games and want to talk about if someone takes an interest in such things. So you being a girl, ask him about his favorite video game. He will turn on and will talk to you for longer than usual.

Question 2: Do you go to the gym?

Ha, even if he has some tiny muscles, you must ask him about his workout and gym routine and must appreciate him about his body. He will fall in love with you. Trust me, if he is going to the gym and have a good or better than regular physique, he will blush and will tell you a lot about gym and workout routine.

Question 3: What you ultimately wanted to achieve in life?

Its great questions because you will know if he is trying to do something in life. What are his ultimate goals in life? If you want to know him better, this is one of the best and most in-depth questions to ask a guy.

Question 4: What you prefer a job or business?

This question has a meaning attached to it. If he is interested in a job or saying, he will prefer to do a part-time business with a job, that means he wants a job. If he straightforwardly says business and only business means he is going to be a businessman in the future. You must ask him what business you have in mind. Or you can ask him these very good questions.

Question 5: Do you have a nickname?

Some guys prefer to be called by nicknames. Guys with cool nicknames will love to disclose their nicknames. If he doesn’t want you to know about his nickname, don’t insist on him. If, for some reason, he disclosed his hated nickname to you, don’t call him by that stupid nickname.

Question 6: What is your favorite movie?

Yes, he must have a favorite movie. He might take some time to think about the movies he liked, but eventually, he will tell you. From movies, you will know his interest. What kind of movies he prefers to watch.

Question 7: What’s the best thing about being male?

There are a lot of things that are best about being a male in a male-driven society. Males have advantages in the sense of strength and other related manly things. He will love to answer this question.

Question 8: What’s the worst thing about being male?

Yes, like advantages, there are some disadvantages too. Ask him this question; he will reply to your question with his thoughts. If you want, you can mix the above question with this question.

Question 9: What you miss the most about your childhood?

We all do stuff in our childhood which we miss while growing up. Asking him this question might bring a smile to his face because he will suddenly go into his childhood memories. You will also know how he was as a child.

Question 10: Who is your celebrity crush?

He’ll definitely like telling you about his celebrity crush, and more importantly, you’ll learn what types of personality he likes. This question is easy to expand; you can add more about movies and related stuff in this question. There is about a 40% chance he might hide his celebrity crush from you. Because you are a girl, and he doesn’t want to hurt your feelings.


Question 11: Which is your dream place to visit?

Dream place to visit on questions to ask a guy
Dream place to visit on Deep questions to ask a guy

He will have some plans to visit his dream place. People usually don’t ask such questions to guys, but guys love to answer such questions. Try questions from our list of best Deep questions to ask a guy.

Question 12: If you can change one thing about girls in general, what would it be?

Yeah, guys wanted to change a lot about girls. What your guy specifically wanted to change, he will tell you. If you have that habit, try to get rid of it.

Question 13: What you can replace your life with a movie star, who would it be?

It’s a fun question and fiction. He will love to replace his life with his favorite male movie star. If you want, you can also ask him some deep type of questions to engage him more.

Question 14: What do you think is best about yourself?

He will show off some of the things about himself, and you get to learn some new things about him. Try and ask him to tell you things you don’t know about him. Don’t worry; it’s a win-win situation.

Question 15: Who was the worst leader in our country?

It’s a serious question for a serious personality. Serious guys mostly love to talk about politics and stuff. You can ask them such questions to start a conversation.

Question 16: What was your favorite time pass as a kid?

He will tell you about some of the embarrassing things he was into when he was a kid.  Boys waste time on different stupid things; they don’t play like girls.

Question 17: What is the most stupid thing you have done?

It’s a great way to explore him. Asking him such questions will help you understand him better in different situations.

Question 18: Which is your favorite phone these days?

Mobile phone on Questions to ask a guy
Mobile phone on Questions to ask a guy

Guys are really into mobile and tech gadgets. He will love to tell you about his new dream mobile. Guys mostly prefer specs instead of look or brand of mobile. So don’t be surprised if he just names some random company instead of Samsung or iPhone.

Question 19: Who is an overrated superstar in Hollywood?

Now you just clicked his mind as a critic. He will explain to you why that superstar is not a superstar. Just listen and have fun and keep the conversation as long as you want by adding related stuff into it.

Question 20: If you were our president for a day? What will you do first?

This question is more like an exam for him. You will see how creative he is at solving such problems. If he is not that interested in politics and issues in your country, he might go blank. If he is a guy who thinks about issues in your country, he will reply with detail. On asking about the first thing, he will choose the most significant problem to solve according to his mind.

Question 21: How you handle pressure in problematic situations?

Get yourself ready to listen to his excellent problem-solving skills. He might give you different examples of how he managed some of the biggest problems. He will inspire you from his words. Do you know about the game 21 questions? You should try that too.

Questions to ask a guy
Questions to ask a guy

Question 22: What is the one thing that pissed you off but turned out to be no big deal?

It’s a fun question to answer, but also very informative. He will tell you about strange things that happened to him in the past. His answer also gives you some sort of analysis about his personality. And yes, it involves storytelling, and guys love to tell stories about themselves.

Question 23: What you want to change about yourself?

Guys are brilliant when it comes to telling something terrible about themselves. He will tell you something cool, but bad at the same time. E.g., I work 24hr a day, and I want to change this habit as it’s not good for health.

Question 24: What event in life has made the most significant impact on you?

It’s one of the best deep questions to ask a guy why it’s the best question because it’s all about storytelling. As I told you before, guys love to tell stories about themselves. He will tell you what changed his life.

Question 25: What you found challenging about people around you?

It’s not a straightforward question; he can come up with lots of different answers to this question. So it’s pretty hard to guess what kind of response he’ll be going to come up with. But it’s a great question to explore his mind.

Question 26: What’s the biggest fear you have?

Yes, we all have fears in our life. Whether those fears are about the world at large or ourselves, this question can lead you, people, to a serious conversation, but remember sharing fears can help to create a strong bond between people. If he is sharing his fears with you means he likes you. He wants you to know about him better.

Question 27: If you were given 10 million dollars to do something that you can’t, will you?

It’s a funny question to ask a guy. And it can tell you about his morals and values. These questions can tell you a lot about his personality. Is he willing to do anything for money, or he can stop himself?

Question 28: Do you think you need to learn new skills?

Yes, we sometimes need new skills. But we have a lot of excuses for why I can’t learn those now. Guys like to think they are experts at lots of things. But to be honest, we are average or below average at most things. For example, just think about how many guys will admit that they are below average drivers. All guys will say I’m an expert when it comes to driving.

Question 29: What is the most stupid thing people do now and will regret later in life?

Just for a second, go back in the past, about 20 years ago, and you’ll find plenty of things that people don’t do now because they think it’s stupid. The same is going to happen after 20 years from now. Ask him this question from our list of deep questions to ask a guy he will love to answer such a question. You should also consider asking him some kind of personal questions.

Question 30: What double standard you think guys have?

Guys have lots of double standards. They mostly don’t admit when it comes to double standards. If you want to explore him deeply, this question is for you. His answer to this question will tell you a lot about himself.


Question 31: What’s your worst restaurant experience?

Food restaurant
Food restaurant on Questions to ask a guy

We all experience different things at restaurants. Your guy probably has a couple of stories to tell you. And who doesn’t like experience gone the wrong story? He will love to tell you about those specific restaurants. He might warn you about those restaurants.

Question 32: Does someone in your life lost his/her respect from you?

It is the best question from our deep questions to ask a guy list. What makes him hate someone? What are the things that matter a lot to him? The answer will open a new personality of him in front of you. He will never tell you this if you ask him directly. It’s an indirect way to know his peak factor of hate, which makes him hate people.

Question 33: Is our government treating people the right way they should?

Yes, it’s a deep question. And it can lead to a long conversation if your guy is more into politics and country. Even if he is not that much interested in politics, he will still reply with lengthy arguments. It is no doubt a deep conversation topic, or you can say a deep question to ask a guy.

Question 34: If you have the option to choose your job for a lifetime? What would it be?

More like a dream job. The job that makes him happy. He will tell you about his inner passion. What he wanted to be. Or you can say you will also know his satisfaction level for his current job.

Question 35: What is your most outstanding achievement so far?

Even if he has done something minimal, you must appreciate him for his efforts. Make him feel proud of what he has done. It should be something positive that doesn’t make him feel proud of negative things.

Question 36: Have you done anything to make our world a better place to live?

It’s a different question from the previous question. The last question was about himself. In this question, you are looking for his inner soul about others, what he feels about other people in the world, how he looks at other people.

Question 37: Who inspired you most in life?

Anyone can inspire us. The inspiring person can be a bodybuilder, runner, any film actor, or a social guy who means a lot to us. So asking for his inspiration will tell you a lot about himself as well.

Question 38: How you deal with haters?

An open question on handling haters. He all have people who hate us for no reason. How we deal with them is an excellent way to know about a person.

Question 39: How you define yourself in a sentence?

This question is more about knowing him personally. The questions are also a fun question. He will love to create a sentence for himself.

Question 40: What is a dream trip for you?

This question is about knowing his dream trip, what is in his mind about a dream trip. You will also enjoy old memories, so use this question when he is in a good mood.

Question 41: Who is your best friend? And why?

It is an excellent question to ask a guy. Guys love to talk about their best friends if they love them. If your guy is not openly talking about his best friend, that means he is not that close to his friends, and it’s a good thing for you. You will get more time even if he has 2, 3 best friends; that wonderful. Guys love to hang out with boys.

Question 42: Suppose if you have kids, do you have any unique life stories to tell them?

If you are interested in listening to his life stories, ask him this question. He might tell you some of the most exciting stories from his life. The question is a supposition, but make you guys laugh.

Question 43: Are you proud of something?

To know him better in the sense of his achievements in life, this is a perfect question. Don’t hesitate to ask. Just ask this question, and he will tell you a lot about his achievements in life.

Question 44: What was the worst gift you have ever received?

Yes, Guys love to gift stupid stuff to best friends on birthdays or special events. Asking this question will make you both laugh. If he hasn’t received something stupid from friends, that means he is not that much attached to his friends, or all his friends are mature.

Question 45: Who is your closest family member?

If you want to know about his family and his relationship with family members, it’s a lovely question to ask a guy.  Just ask this question, and he will definitely like your interest in his family.

Question 46: Who is your favorite anchor in TV shows?

Yes, it’s a generic question, but it’s an excellent way to interact and have something to talk about instead of looking at each other with awkward silence.

Question 47: Do you daydream? What you mostly dream of in the day?

All guys do daydreaming about different things. It’s an exciting topic to talk about with guys. Initially, he might not tell you about his daydreams, but if you just help him with your stories, he will open up.

Question 48: What’s your favorite joke?

If you guys want to laugh, ask him this question. Listen! If you already knew about the joke he was trying to convey, react like you just heard it. Try to let him feel that the joke was hilarious and be natural, don’t fake it.

Question 49: Do you believe in myths, e.g., mermaids do they exist?

It’s an interesting deep question to ask a guy. Such questions can be answered with different thoughts. Let him speak about the topic. You can prolong the conversation by adding a few more myths in your talk.

Question 50: Can you tell in advance if someone is going to be successful or failure?

It might look like a straight and straightforward question, but in reality, it’s more about his observation in people how he observes things around him. On what parameters he judges people. What is his definition of success? How different he thinks.

Question 51: What’s the most fun experience you’ve had?

Person in boat fun experience
Person in a boat on Deep Questions to ask a guy

It’s a lovely question to ask a guy from our list of questions to ask a guy. Why? Because he is going to tell you some of the dumbest experience he had and may claim it as fun. Don’t worry, just laugh or smile.

Question 52: Do you have any weird habit that makes people annoyed by you?

If you are new to him, he is not going to tell you about his bad habits. But he might tell you some good looking bad habits.

Question 53: What food you like the most, and why?

Yes, all guys love to eat good food. Every one has his taste, so we don’t the answer. But this question will help you know about his choice of food.

Question 54: If you can go inside a video game, which game you want to visit, and why?

Even if a guy is not a gamer, he must have played many video games. Guys love video games and enjoy doing things that are not possible in reality. He will enjoy answering this question.

Question 55: What is your best physical feature?

He might reply with a little blush, don’t worry, and enjoy his answer. We don’t know the answer because it is a personal thing for that specific individual.

Question 56: Do you believe in the concept of “Real man”?  Are you consider yourself as “Real man”?

One thing you as a girl must know, what so ever your guy reply he is a real man inside. Real man means he is the king and wants you to be her queen. He doesn’t want you to be his king.

Question 57: Have you ever had any trouble with the law or got arrested for something in the past?

It’s a must question to ask a guy. He might not lie, but he can, depends upon person to person. You must know about his history with law enforcement.

Question 58: Do you like prank videos?

He is going to say yes because guys love to watch comedy, especially pranks. Because pranks are something, they wanted to do with others.

Question 59: Do you think it’s essential to keep up with the news, or should we not care?

There are two types of guys one who doesn’t miss any news, one who doesn’t care about the news. To know his kind, you must ask him this question.

Question 60: According to you, what were some of the big mistakes made in history?

It’s just a generic question to know about his interest in history. If he had some interest, he would reply, and if he doesn’t know much about history, he will say straightforwardly say, I don’t know. Don’t use this question as a starter.

Question 61: Do you like waking up early or staying up late?

It’s one of the best questions to know about his habits.

Question 62: Do you prefer staying home or hanging outside?

Some guys love to stay home or do things that are related to staying home, e.g., playing video games. On the other hand, some love to move around with friends and have fun.

Question 63: How would you describe me to others?

If you want him to say good things about you, ask him this question. If he is a funny guy, he might make a joke about your question and say thinks that you might not enjoy listening about yourself.

Question 64: What’s the most incredible thing you’ve ever heard about yourself?

He is going to love this question. And he will love to reply.

Question 65: What is that one specific thing that you can do without getting bored?

What he enjoys doing in free times. What kind of activities he prefer to do for the sake of enjoyment.

 Question 66: Which describes your personality with a word, e.g., decent, funny, Cool, or naughty?

He will tell you the hidden truth about his personality. He will not lie on such questions.

Questions 67: Do you regret buying something that you liked?

Why he disliked something that he liked before? It happened with us all. We all have faced such a situation from time to time. Why he faced such a problem, his answer will let you know better.

Question 68: How good are you at convincing people?

Only your guy knows the answer to this question. Suppose his argument convinced you that he could convince people. Believe him!

Question 69: Which is your dream car? And why?

Dream Car for guys on Questions to ask a guy
Dream Car for guys on Questions to ask a guy

If he had the option to pick between his dream car or dream girl, he would prefer a car. Guys are crazy about cars. Don’t worry; this question is just to make him happy. He will happily reply to your question.

Question 70: Did you ever regretted after making a decision?

It’s possible and very common. We sometimes make decisions that are not as good as we taught. Asking him such a question makes you more close to him.

Question 71: If you have to give a lecture on something which topic you will choose?

If you secretly want to know about his knowledge of our interest in topics. You can use this question to get the exact information out of him.

Question 72: Where do you see yourself in five years?

You must know about his plans. What are his dreams, and can you adjust to those plans are not. You must ask this question to your guy.

Question 73: How was your childhood?

To know appropriately about his personality, to understand him better why he is as he is. It is one of the must-ask questions in our Deep questions to ask a guy list.

Question 74: Do you think movies influence us?

It’s an excellent topic to talk about with a guy. Yes, movies do influence our behavior and our thinking. Ask him this question from our list of questions to ask a guy, and he will love to describe his thoughts on the topic.

Question 75: What are you not so good at?

It’s a difficult question for a guy to answer. Because they think they are good at everything. But some people know what they can’t do.

Question 76: What was your favorite cartoon character as a kid? Do you still like that character?

As a kid, guys love cartoon characters, but even adult people watch cartoons, and they call it anime.

Question 77: Anyone from your friends or family who have done something special for you?

This question is more about knowing him personally and his family. Ask him this question; someone close to him must have done something for him.

Question 78: How you handle people who comment on your things?

We all have faced such situations from time to time. How he managed his way from people’s comments will tell you more about his personality.

Question 79: Do you like beef or chicken burger?

He might like both, and that’s a good thing. Just to know his taste, it’s a good question. Even when you guys can’t decide what to eat, ask him this question, and it will make his mind. We can’t choose when we have multiple options to eat. So, don’t use various options. If you are in the mood to eat burgers, just ask about burgers. The same goes for pizza etc.

Question 80: Who is your favorite villain of all times?

It’s an exciting topic to talk about with a guy. Guys sometimes love villains more than the hero in the movie. So asking him this question might surprise you.

Question 81: If you were given $100 000 to buy something instantly, what will you buy?

If you want to know and talk about his ultimate wish or desire to buy something that he can’t, it’s the best question to ask a guy.

Question 82: Does anyone has ever tried that stupid “knock-knock…” joke on you?

Prepare any knock-knock funny joke to make him laugh. Such stupid questions work best when he is not in a good mood or having a bad day.  Upon his answer yes/no, whatever just says, “ok, then let’s try one.”

Question 83: According to you, which sports are boring?

Everyone has his own taste in sports. He can even find football boring, which is fun for many. Ask him this question to know him even better.

Question 84: How good are you at arm wrestling?

Arm wrestling is a common sport for men. Guys do arm wrestling just to show strength and for the sake of fun with their friends. It’s an interesting question to ask a guy.

Question 85: Do You like buying stuff that is considered only for girls?

Not too stupid like buying pink colored stuff etc. If you think these questions are not working for you, why don’t you try some funny questions? We are sure he is going to laugh hard on these questions.

Question 86: Name any weird thing that you used to eat as a child?

No doubt, kids eat whatever they found on the ground. The question is to bring back his childhood memories. He might tell you related stories. Moreover, you guys are going to have a good laugh on this question.

Question 87: Do movies made you cry?

Although it’s against the manly-hood to cry, yes, guys do cry while watching movies. Most Guys don’t admit that fact.

Question 88: What small things you always loved doing?

Sometimes tiny things make us happy. Guys also do little stuff to be happy. Ask him this question, and he loves to tell you about his little things.

Question 89: If you were given 2(Paid) hours off from your job, where would you like to spend your free hours?

It’s not possible, but an excellent question to ask a guy from our collection of Deep questions to ask a guy. He will enjoy answering this question.

Question 90: What you recommend others to do at least once before dying?

This question will expose his inner self to you. What he thinks everyone should do.

Question 91: If you get a chance to move elsewhere in the country, which city would you like to move to?

If he is planning to move somewhere in the future, he must have planned it already in his mind. You must ask him this question to know his plans without directly asking him.

Question 92: Do you have any clear childhood memory?

childhood crush deep questions to ask a girl
Childhood crush on deep questions to ask a guy

We don’t remember everything while growing up. But some events are so much deep that we can’t forget them.

Question 93: What is your all-time favorite idiom?

If you guys want to smile, just ask this question. It’s a light question and easy to answer the question.

Question 94: What was your favorite website when there were no social sites? e.g., Facebook, Twitter, etc.

If he is from the ’90s, he must know the answer to this question. The new generation doesn’t know much about Msn, Yahoo messenger or chat rooms, etc.

Question 95: Do you hate any celebrity?

Yes, we do hate people for different reasons. And celebrities are too public, so people often hate them for other things.

Question 96: What you notice most in people?

Baby girl | questions to ask a girl baby

We all observe different things while meeting with someone. But everyone has his style of observation. You must know this about your guy how he notices people.

Question 97: What specific thing quickly makes you angry?

To know him better in the sense of anger, you must ask this question to your guy. It’s a fundamental question for you, from our list of Deep questions to ask a guy.

Question 98: Suppose you were alone at home, and your home got on fire. You can only save one thing, what would it be?

If you are curious to know the most important thing for him in his house, simply ask this question to him.

Question 99: What weird food combination you liked the most?

It’s possible because we sometimes make our flavors in food.

Question 100: Have you ever traveled somewhere outside our country?

Before starting a relationship, you must know his travel history. With this question, you will see if he is a frequent traveler or has not visited anyplace outside your country.

Question 101: What is your favorite mobile game?

Just a fun question to ask a guy. He’ll also enjoy describing the game to you.

Question 102: What is the Worst Advice you received from someone?

Sometimes people around us misguide us and gave us the wrong advice. We never forget such things and also want to save others.

Question 103: What is the best advice you received from someone?

Like the worst advice, we also get useful advice from people around us or our friends. We also feel great while sharing that piece of advice with others.

Question 104: What’s the most useful skill you’ve ever learned by yourself?

Guys enjoy learning new skills while they are teenagers. After that, the new learning process slows down, which useful skill he had might help you in the future.

Question 105: What is your favorite trend of all time?

Trends are very common these days due to social networks. E.g., fidget spinners, etc.

Question 106: What was the last stupid thing you heard from someone that made you laugh?

If you guys are in the mood to laugh, it’s one of the best questions to talk about and laugh.

Question 107:  Do you believe in global citizenship?

Global citizenship means the world as a single country. Giving rights to people to travel or live anywhere in the world. Find out his thoughts on global citizenship.

Question 108: What can you eat best at $5?

Suppose you want to hang out with him and don’t want him to spend too much on you. Ask him this question and let him take you to have that thing in less than $5.

Question 109: Which movie has the best villain portrayed as a hero?

Sometimes movie villains are portrayed as heroes. Ask him this question to know about his interest in movies.

Question 110: If you can go back in the past, which invention would you like to name for yourself?

It’s just a fiction based question to have an interesting discussion with your partner.

Question 111: What you have as background on your laptop?

Guy with mobile and laptop on Questions to ask a guy
Guy with mobile and laptop on Questions to ask a guy

This question is all about knowing more about his likes and dislikes.

Question 112: Do you know how to play any card game?

Guys mostly play such games for the sake of fun with friends, so he might know a few games.

Question 113: What is your favorite board game?

There are different board games in the market, and everyone has his taste in board games. Ask him about his favorite.

Question 114: What was the worst dream you had?

We all had different types of dreams; it an excellent topic to talk about.

Question 115: Do you have something that makes you special or unique?

It’s a very different kind of question to know his inner abilities that he usually doesn’t tell others. It can be some simple act.

Question 116: Which famous quote are you tired of hearing?

It is a simple question to ask a guy from our list of questions to ask a guy. He will reply to you with something interesting, and you guys might end up laughing.

Question 117: What would be the last food you’d like to eat before you die?

It’s a fun question to know about his favorite food of all time.

Question 118: How passionate are you about reading books?

Suppose you want to know about his book reading side. Is he a book reader or not? His answer will open your eyes in a minute.

Question 119: If you have to appreciate, how would you appreciate someone?

It’s good to know about his personality in detail if you are looking for his appreciation style better to ask him directly instead of asking with puzzles.

Question 120: What common ingredient you hate the most?

Guys or even girls hate stuff that is regularly used in cooking. What he hates is good to know before inviting him to dinner at home.

Question 121: How well you know about cars?

Most probably, he is going to spit a lot of information on cars. Be ready to listen to all if you are interested in listening to him for a more extended period. It’s a good question. There is about a 30% chance he knows nothing about cars.

Question 122: Why some people are homeless?

It’s an excellent question to ask a guy. You will know about his observation power.

Question 123: Do you like tattoos are not? What the weirdest tattoo you have seen so far?

Guy with tattoo
Guy with Tattoo

Some people don’t like a tattoo at all. Some people have the most stupid tattoos. Just to have a fun conversation with your guy, it’s a great question to ask him from our Deep questions to ask a guy list.

Question 124: Do you think you can be an actor? If yes, what kind of roles do you think you can do better?

Its assumption based question but have a lot of fun in it. Guys imagine themselves in movies all the time. It’s an excellent way to know about his imaginations as a hero.

Question 125: What’s the weirdest thing that has happened to you?

Again if you guys want to have a fun conversation, it’s a good starting question to ask a guy.

Question 126: What movie would be better if you could add something to the story by yourself?

To know his creative abilities and also to have some fun, it’s a very cute question to ask a guy. Don’t hesitate to ask such questions to guys.

Question 127: What you think is going to be illegal soon in our country?

It’s a bit tricky question. If he doesn’t know the answer, prepare something yourself so that you can connect to the conversation instead of looking stupidly at each other’s face.

Question 128: If you could become anything, what would you like to become?

Again a fiction based question, but an exciting question to ask a guy.

Question 129: Are you bad at any sports that you regularly play?

It’s just a random question to ask a guy. You can ask whatever you like to guys as they respond well to girls.

Question 130: Do you still enjoy something childish for people?

Yes, guys do stuff that people consider as childish, but still, It’s a funny question that you can ask a guy. You both are going to laugh hard.

Question 131: What’s the most fun thing you have done in your life?

If you are interested in listening long or short funny stories, it’s an excellent question to ask your guy. Ask him this question and let him speak.

Question 132: Do you want to learn any musical instrument?

If he is already good at something, he will not waste time and tell you immediately.

Question 133: What is your best pickup line?

Guys have special moves when it comes to picking up lines. Ask him this question to have a good laugh.

Question 134: Do you have an ultimate goal to achieve in life? What’s your plan to achieve your goal?

The question is more about his future personal plans on how he is approaching his plans. It is a deep question to ask a guy.

Question 135: What are some big first world problems?

If you want to have a decent talk with your guy, it’s a very decent question to ask a guy.

Question 136: Do you believe in saving money or spending money?

Guy with money
Guy with money on Deep Questions to ask a guy

It is an excellent question for the long run. You must know this side of his nature; it will save you from more significant problems in the future. Some guys don’t care about saving money. They love to spend whatever they have in their pocket. It’s not a good thing.

Question 137: Have you ever faced any injury?

Just to know about his medical history, you must ask such a question to save yourself from any shock in the future.

Question 138: If the earth was about to end and people have the choice to move on any other planet, will you stay or move?

Again a fiction based question about the end of the earth, you guys can talk about this topic for hours and hours.  Get a bit more detail about the end of this world to have a proper conversation.

Question 139: Have you ever met a stranger who made your day?

It can happen, we meet strangers daily, and they do little stuff that can make us happy.

Question 140: Do you know any magic trick?

Yes, not everyone, but you can say at least 40% of guys know card tricks.

Question 141: If you open a business, what will you name your business?

It’s a good question to know about his business plans and also to have some fun.

Question 142: What you idealize the most in life?

Just to know his side of life, this is one of the cutest questions to ask a guy.

Question 143: Do you feel a little jealous of someone is super talented?

The question is designed to know about his inner self.

Question 144: If you could add any rule on social networks, what would it be?

We all face different problems on social networks and want to change certain things on those networks. It’s an excellent question to ask a guy.

Question 145: Who is your favorite funny movie actor?

Funny is a different category we all love to watch. Everyone has their own choice; it’s a delightful question to ask a guy.

Question 146: Do you have any little wish that was not fulfilled yet?

If you can fulfill his wish, you should.

Question 147: What’s the most boring hobby you found familiar in people?

Just laugh at his answer if he is right. No, doubt its an excellent interesting question to ask a guy.

Question 148: Do you have any unique story for your children? “When I was young, I used to …”?

It’s a very funny question to ask a guy. He will laugh while replying to your question.

Question 149: What’s the best part of the weekends?

To have a sweet chit chat, it’s an excellent smooth question to ask a guy. Ask this question, and you will enjoy his answer.

Question 150: Do you know about something really strange that people do?

People are so strange when it comes to doing stuff. He must have heard something strange or have seen people doing something really strange for him. It’s a good interesting question from our list of Deep questions to ask a guy.


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Top 9 Deep Questions to ask a guy
Top 9 Deep Questions to ask a guy

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So these were the 150 Deep questions to ask a guy. We tried to keep things simple and interesting at the same time. I hope you enjoyed reading all these questions. As mentioned before, do not try to copy us word by word, but try to keep your natural style of asking questions. If you still hungry for more questions to ask a guy, more articles are given on our website.

Warning: Don’t just copy our questions word by word. Try to ask in your natural style. Just try to pick the meaning from questions. Don’t hesitate to be confident, and remember, it’s not a bad move if you, as a girl, start the conversation. If you like him, just start the conversation.

You don’t have to use all of these questions. Try to ask the relevant questions to you guys. You know your guy better. Chose those questions which are better for him.

There is no right or wrong in questions. You can pick any question that you like, or you think he is going to like. I just chose the right question from our list of questions to ask a guy.


These were all the questions; I hope you guys enjoyed reading these. Don’t forget to give us your feedback.

Thank you

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