91+Deep Questions To Get To Know a Guy (What You Should Know)

Deep Questions To Get To Know a Guy

Here’s a great list of one-of-a-kind deep questions to get to know a  guy. They are intended to start an interesting conversation, so some of the questions are a little off the beaten path. Remember that every guy is unique, so pick and choose which deep questions you believe will work best for your guy or questions that you really want to know the answers to.

You’d be surprised at which questions a guy finds interesting. Even if a question appears to be something he would be uninterested in, it may be worth a shot. Before we begin, keep in mind to ask lots of follow-up deep questions to learn more and keep the conversation going.

Questions to Get to Know A Guy

A list of probing deep questions to ask a guy to get to know him better. Without further ado, here are 91+ deep quality questions to get to know a guy!

1. What was your most memorable “drop-the-mic” moment?

Who doesn’t enjoy telling a great story about themselves? These deep questions to get to know a guy will allow your guy to tell you a good story and is a great way to get him talking. It will also tell you what he is interested in and what he considers important.

2. What childhood activity do you still enjoy?

We all have things from our childhood, and I’m sure he does as well. He may not admit it, but he still enjoys peeing in the snow and building sandcastles. This deep question is likely to elicit some amusing responses. Remember that you don’t have to limit it to just one childish thing; you can get him to list several.

3. What is your biggest concern?

We’re all skeptical. Whether they are about the world as a whole or about ourselves. This one can really spark a serious discussion, but sharing doubts can be a great way to build a strong bond between two people.

4. Who has totally lost your trust?

A great set of probing questions to see what values he holds deep. Also, as there have been many celebrities who have fallen from grace, this is a great conversation starter.

5. What movie do you wish you could see more of in your life?

Another question that is entertaining to answer and sparks a truly unique conversation. Just keep in mind to discuss the minor details that would be altered as well. Investigate how everyday life would change if it were more like the movie he chose. Don’t be afraid to take it to absurd levels.

6. How many phones have you broken or misplaced?

A seemingly simple question can sometimes lead to a lengthy discussion. That’s because there’s usually a story behind every broken or lost phone. That, or he’s just clumsy or forgetful, which is also useful to know.

7. Who or what is your adversary?

We all have things or people that we despise. I’m sure he does as well. And, since everyone enjoys discussing what irritates them, this is a great question to start a conversation. If you want, you can encourage funny or silly responses, such as jars that don’t open or YouTube videos that load the ads but not the video. You can easily transition the conversation to a lighter rant about general annoyances.

8. What is the most pointless thing you can think of?

What kind of hidden abilities does he possess? This is always great because he can usually show you. We all have silly and useless skills that you can now learn about!

9. What are the worst and best aspects of being a man?

How well do you understand what it’s like to be a guy? Now is your chance to learn more. I believe you’ll be surprised by some of the responses you’ll get from the man you’re speaking with. You could also try shifting the conversation to some minor annoyances about being a guy. These deep questions to get to know a guy are great because they’re a lot of fun to answer and you’ll probably learn something new.

10. What is the most common mistake that people make?

There are a lot of different answers to this one, so it’s difficult to predict what he’ll say. But it’s a great little question to start a conversation or at least bring up some complaints about which you can both commiserate.

11. What would you NOT do with $5 million?

This one is a lot of fun to answer. It can also reveal a lot about the man. You can learn which morals he values the most and which activities he despises.

12. What was your most daring bet that paid off?

He’s probably never been asked this question before, so give him some thought time. You’ll almost certainly get an interesting response, either a story or a fact about him that you didn’t know.

13. What would you do if you could only learn one magic spell and it could only do something mundane and boring?

A fun question that can elicit some really creative responses. Unclog a drain, make toast slightly more brown, unjam a copier, and so on. You could continue the conversation by attempting to come up with an incantation to go with the spell.

14. You awaken unexpectedly in the middle of the night. What is the most terrifying sound you could hear after waking up?

It’s fantastic because it may provide you with some insight into what he is afraid of. Either that, or you’ll give him the opportunity to make you laugh if he wants to turn it into a joke. In any case, it’s a fun deep question to get to know a guy and one that allows for easy follow-up questions. You can discuss increasing the dread of the situation, talking about his other fears, or perhaps trying to find fears you share.

15. What high-level position do you believe you could get with no experience and no one would notice?

This question has many possible answers, but to make it more interesting, discuss how he would prevent people from discovering he was a fraud. Sure, it sounds like a bad comedy movie plot, but it’s a fun question to answer.

16. What would be the ramifications of a scientific breakthrough that increased human life expectancy to 500 years?

You two can skip this one if you’re not in the mood for a serious debate, but I think you’d be surprised at how many guys will actually answer a question like this. You can talk about how societal norms might change or how they might affect technological progress. There are so many different ways to answer this question.

17. What is a movie that you can watch over and over again and never get tired of?

He’ll enjoy telling you about his favorite movie, and you’ll learn about the types of movies/shows he enjoys. This question lends itself well to further discussion because you can start talking about favorite movies and TV shows, as well as movies or shows you despise.

18. How would you design and build a treehouse, and what would it contain?

This is probably my favorite of the deep questions to ask to get to know a guy. It’s pure inspiration. It’s fantastic because every guy secretly desires a badass treehouse getaway for himself. I’m not sure what it is, but I’ve never met a man who disliked tree houses.

19. What is the most fascinating fact you know?

He gets to show off some of his knowledge, and you get to learn some new things. Try to persuade him to tell you something you don’t already know. It’s a win-win situation.

20. Which celebrity would make the worst country leader?

What makes this question so interesting is imagining what the celebrity would do if they became leaders, and what kinds of laws they would enact. This one is always a good laugh. Keep changing out the celebrity to keep the conversation going.

21. What were you really into when you were younger but now consider ridiculous?

Discover what embarrassing things he was into as a child. Great fodder for some lighthearted teasing later on.

22. Which historical figure was not as remarkable as most people believe?

I understand that not everyone is interested in history. Even if he only has a passing interest in history, he’ll likely enjoy this question. After all, “great men are rarely good men,” as the saying goes.

23. You are in charge of popularizing insects as a food source. You have one billion dollars to accomplish your goal. How do you go about it?

Here’s another inventive one. You can see how quickly he thinks on his feet and how creative he is at problem-solving. Sure, it’s a random question, but it’s a fun way to brainstorm some creative ideas. Furthermore, working together to solve a problem is a great way to have a natural conversation.

24. What is the most stressful situation you’ve ever been in, and how did you handle it?

This question, like the drop the mic moment question, will allow him to tell you about a story that is important to him. Just keep in mind that there will almost certainly be some exaggeration and embellishment when he tells you the story, even if he doesn’t mean to. After all, memory is a seriously flawed construct!

25. What was something you were really worried about that turned out to be nothing?

It was a fun question to answer, but it was also very informative. You can find out what types of things irritate him, as well as how high-strung or laid-back he is. Plus, it’s another opportunity to tell a story, and almost everyone enjoys telling stories about themselves.

26. What topics have you had enough of hearing about?

With a 24-hour news cycle, there is always some news story or phenomenon that has passed its peak of interest. Asking him this question will reveal what types of things he isn’t patient with, as well as what topics to avoid in conversation.

27. What three events had the most influence on who you are today?

One of the best deep questions to ask a guy to get to know him. It will tell you a little bit more about his past, how he sees himself, and what he values. It’s also fantastic because there are a plethora of follow-up questions you can ask about these pivotal events in his life.

28. What do you believe you know a lot about but most likely don’t?

Everyone likes to think of themselves as experts in a variety of fields. But, let’s face it, we’re only average or below average at most things. Consider how many people will claim to be above-average drivers. A little self-reflection is always beneficial.

29. What is society doing now that will be laughed at and ridiculed in 20 years?

Think back 20 years and you’ll find plenty of things to laugh about. And that’s how it’ll be in 20 years. People will be laughing and mocking a variety of current trends. So, what do you think the “future you” will look down on?

30. What double standard is ridiculous and must be abolished?

There are numerous examples of double standards to choose from. So it’s time to find out what issues he thinks are important, or if he doesn’t care about societal issues at all.

31. What is your worst customer service experience, as a customer or as an employee?

He most likely has a few. And who doesn’t enjoy a good customer service story gone wrong? If he’s worked in customer service, he’ll undoubtedly have a few. And if he hasn’t, he’s probably heard some horror stories about customer service from the other side of the table.

32. What is the most effective way for a government to maintain control over its citizens?

So, I debated whether or not to include this one on the list. It’s a little deeper and more serious than the majority of the other questions. So, if it’s not appropriate, feel free to toss it out. However, if either of you is interested in politics or history, it can lead to some very interesting conversations.

33. If you had to dedicate your life to a single cause, what would it be?

We all have causes that we are passionate about. You’ll be able to figure out who he is now. You’ll also learn how involved he is in charity or volunteering. But, aside from all of that useful information, it’s still a fun question to answer because it really contrasts what we do in our daily lives with what we want to be.

34. What would be your greatest accomplishment if you died today?

A fantastic introspective question that everyone, including you, should consider. It’s easy to get caught up in the minutiae of daily life and forget that we’ll all die one day. It’s important to remember that life is meant to be lived.

35. How have you contributed to making the world a better place to live?

This one may or may not have the same answer as question 34, but it is most likely related to it. Overall, it’s a great deep questions to get to know a guy and find out; some of the things he’s done and the things he thinks are important.

36. Who are some people you’ve only met once but who have left an indelible impression on you?

You are the same person you were five years ago, except for the places you’ve been, the books you’ve read, and the people you’ve met, as the saying goes. So, who has he met who has changed his perspective on life?

37. What do you believe is the most common complaint in your country?

Essentially, an open door to a political debate. Which, depending on what you’re after, can be good or bad. As a result, use this question with caution!

38. What is the one question you can ask someone to learn the most about them?

A fantastic question on many levels. It takes some thought to respond, but it can lead to some interesting conversations. He’ll ask you a question that you can both answer, and you can also ask him your own. You’ll both learn a lot more about each other as a result.

39. What was your most recent near-miss?

This one is primarily intended to persuade him to tell a good story. However, it can sometimes elicit emotional memories, so use this question with caution. Still, deep questions are a great way to get to know a guy.

40. What life stories will you tell your children (assuming you have children)?

Here’s another good one because it can lead to some really good stories, which he’ll enjoy telling and you’ll hopefully enjoy hearing.

41. If you could become the world’s foremost expert in one field, what would it be?

Perfect for learning more about his interests and possibly some of his goals. Who knows, maybe you’re both interested in the same thing, or maybe you’ve never heard of it. In any case, it’ll give you both plenty to talk about!

42. Tell me about the worst purchase you’ve ever made.

It’s a strange question, but it can lead to some very interesting answers. Plus, you’ll at the very least learn about something you shouldn’t spend your money on!

43. What did you think was ridiculous before you tried it?

I’m sure you’ve heard of green eggs and ham. Now you can learn about his green eggs and ham moment. We’ve all been in situations where what we thought was stupid turned out to be incredible. And who knows, maybe you’ll get to try something new and exciting!

44. Which author is your favorite?

Okay, this question is a little generic, but it allows you to find out how much he enjoys reading and what types of books he enjoys. It’s also useful to know if he’s not into books or doesn’t have a favorite author.

45. What do you dream about when you’re daydreaming?

What is going through his mind when his eyes glaze over? Now is the time to find out!

46. What do you believe despite the fact that you know it’s probably wrong?

Sure, it’s similar to the question about doubts, but it can lead to some really interesting answers. The responses can be a little serious and dark, but I think this is a great question. It’s a question that everyone should ponder from time to time. We should always be questioning our beliefs and seeking the truth, even if it is uncomfortable.

47. What indicators lead you to believe that someone will be successful?

This appears to be a simple and straightforward set of deep questions to get to know a guy, but it actually reveals a lot about the qualities he values in other people. It can also reveal a lot about what he considers to be a success.

48. What has been your most unusual but enjoyable experience?

As a guy, this is an excellent question. Why? Because, as a guy, I can tell you that in the name of having a good time, we do some incredibly stupid and unusual things.

49. What was your oddest childhood habit?

Every child is unique in their own way. When he was a kid, he was also odd. So you can now learn some embarrassing and probably amusing details about his childhood.

50. What is the most repulsive food?

Yes, this is an unusual way to start the night. But it appeals to me. And it’ll almost certainly result in some amusing responses.

51. What video game do you wish existed in real life?

This is a good one if the guy likes video games, but not so much if he doesn’t. If they are, make sure to ask them a lot of questions about why they enjoy the game so much.

52. What is the most amusing prank you can pull on someone?

This one can be useful for determining whether the guy is a prankster and, if so, what kinds of pranks he finds amusing.

53. What was history’s biggest blunder?

If he’s interested in history, that’s fantastic; he’ll probably think about it for a while before responding. Even if he isn’t interested in history, he’ll probably be able to come up with a decent answer.

54. How do you define friendship?

This one can be a little deep, especially if you’re just trying to be friends with him, so skip it if you want to keep things more casual. However, it is a good question to find out how important friendship is to him.

55. What is the worst thing you could be afraid of?

There are a plethora of phobias out there. If you want to look at a list of phobias.

56. For whom or what do you always make time?

It could be a relative or a friend, a hobby, or something completely different. Whatever or whoever it is, it or they are most likely very important to him.

57. Name two things on which you will never spend money.

There are a variety of responses to this question, and his responses can reveal a lot about his personality or, at the very least, his worldview.

58. What is it that you need to rant about or get off your chest?

We all need to go on a rant every now and then. Why not give him a chance to express himself?

59. What has been your best bad decision?

I’m sure he’s made a few bad choices that he wouldn’t change. It’s time to figure out what those bad decisions were because they usually have a good story behind them.

60. Could you give a thirty-minute impromptu lecture on anything?

Whatever topic he chooses, he’s most likely an expert on it and has spent a significant amount of time researching it.

61. What can a movie do to make you want to get up and leave?

What is the limit that must be crossed? Is it a gradual escalation of cheesiness? Maybe something obnoxious or disgusting?

62. When you were a kid, what was your favorite cartoon?

Who doesn’t enjoy talking about their favorite childhood memories? Everyone enjoys reminiscing from time to time, and chances are he will as well.

63. What are some things that people have done out of the goodness of their hearts to make your life better?

This question is excellent for eliciting his feelings of gratitude for what others have done in his life. And if he does not believe that anyone has selflessly done anything for him, he has either had a REALLY ROUGH life or does not value the things that people do for him.

64. Can you think of any amusing euphemisms for everyday activities?

If you and your partner are both creative, this question can be a lot of fun. Humans have a plethora of euphemisms for everything; now it’s time to invent some new ones!

65. What do you own that attracts a lot of attention?

Maybe it’s a car, a watch, a shirt, or something completely different. Whatever it is, he most likely has a few stories about it or the people who comment on it.

66. If you could level up in life the same way you do in video games, where would you put your next skill point?

There are so many to choose from! Strength, intelligence, dexterity, constitution, charisma, or perhaps he would like to improve a skill he already possesses. This is a fun question, but its applicability depends on his level of geekiness.

67. What have you done wrong for the majority of your life and only recently discovered the correct way to do it?

These deep questions to get to know a guy can be amusing. The funniest stories are about people who learned how to do something incorrectly as children and didn’t learn the correct way until much later in life.

This question can be quite revealing because it elicits the specific values that he considers to be valuable. It will reveal a lot about how he perceives the world and his place in it.

69. What is your ideal burger?

It’s a very American question, and it’s mostly for fun. But it will tell you a little bit more about what he likes and dislikes.

70. Who is your favorite fictional villain?

You could also ask about a favorite hero, but it’s usually more interesting to learn about which villain he admires. It could be because he thinks the villain has a valid point, or because he thinks the villain is cool.

71. You’ve been given up to $300,000 to make one room in your house or apartment ridiculously amazing; which room do you choose and what improvements do you make?

A great question for eliciting creativity and determining what his ideal space would look like. Also useful for determining what kinds of things he wants or believes he wants.

72. Have you ever seen someone play the “Do you know who I am?” card?

Sure, you see it in movies all the time, but does it happen in real life? Perhaps they or you have seen it in person. And I’m sure it would make a great story to tell.

73. What are some boring games or sports, and how can they be made more interesting?

It’s a lot of fun to collaborate on rule additions and edits for this one. For example, in golf, there is only one ball, and all of the players must fight over it while attempting to hit it into the hole.

74. What game do you consistently lose?

Guys play a lot of games, whether it’s sports or video games. You can now find out which games he is the worst at.

75. What activities do you enjoy that are traditionally considered feminine?

Gender identities and roles are evolving. And this question is a good way to get a sense of his thoughts on masculinity and gender in general.

76. What was the strangest thing you ever ate as a child?

Kids eat strange things. Yes, I did. You most likely did as well. And he most likely did as well. It’s time to laugh at some of your childhood oddities.

77. If time was not an issue and you had an unlimited amount of time to master a skill, what would it be?

This is a great question for learning more about his interests and what he wants to do/be.

78. What would you have a tourist do if you wanted to show them the local flavor of where you are from?

This one can be a lot of fun, and it works whether you’re both from the same city or from different cities. It will tell you or let you know what it was like growing up where he did, or if you are from the same area, you can have fun brainstorming together and possibly getting some good ideas for places to visit.

79. If you could make everyone in the world believe one thing (whether it’s true or not), what would it be?

Another is excellent for pushing one’s creativity. Also, feel free to think of more than one thing to make the discussion a little longer. This question has the potential to spark some unexpected conversations.

80. What are you so bad at that you’ve given up on ever doing it again?

It can be endearing to hear and talk about failures, and this question is excellent at eliciting failures without being overly critical of them.

81. What was the most recent film that made you cry?

This question may give you an idea of how sensitive he is. Or, at the very least, how frequently he cries at movies.

82. What minor details do you always worry about?

No matter how hard we try, there are always minor details that we should not be concerned about, but we do.

83. If you had an extra four hours in your day, what would you do with them?

Chances are, whatever he mentions is something he wishes he could do now but lacks the time or energy to do.

84. What is something that everyone should do at least once in their lives?

A good question to start a discussion about meaningful experiences he has had or wishes he could have.

85. Where would you like to relocate?

Sure, we all love our hometown, and he most likely does as well. But there might be somewhere he’d rather be. Whether it is in his own country or another.

86. What is your earliest recollection?

Memories are strange, slick things. Most of our memories are flawed, especially those from our childhood, and some are completely false. But that doesn’t mean they can’t be used to spark a lively discussion!

87. What do you believe is the most perplexing idiom for English learners?

So, this is a strange one. If you don’t think it will fly, don’t do it. An idiom is a saying that takes on a meaning other than its literal meaning. For instance, he escaped a bullet or she is caught between a rock and a hard place.

88. What are some websites that you used to frequent but no longer do?

Ah, our personal website cemeteries. We used to visit them almost every day but haven’t thought about them in years. It could be Myspace, Livejournal, or Newgrounds. But, whatever the site, he has one or three. And it’s always enjoyable to reminisce.

89. Which celebrity would be the worst to dine with?

This is a play on the age-old question, “Who in history would you most like to have dinner with?” Sure, it’s a bit negative, but at the very least you’ll learn who his least favorite celebrity is!

90. What is something obvious that you didn’t notice until it was pointed out to you?

You know, the kinds of things that make you feel stupid and make you think, “Oh yeah, that makes sense.” It’s always fun to share embarrassing stories and laugh at our former selves.

91. What minor irritation irritates you more than it should?

This one is useful for determining his pet peeves and how picky he is about certain things. And it’s always useful to know what irritates people. It is up to you whether you use that knowledge for good or evil.

92. If your house caught fire, what is the one thing you would most want to save? Assuming that any people or animals have already escaped safely.

What are their most prized possessions? Make sure to ask follow-up questions to find out why they chose that item, and don’t be afraid to ask what their next move will be.

93. What flavor combination is unusual, but do you enjoy it?

People enjoy a wide variety of foods, and he is likely no exception. Who knows, you might just discover your new favorite flavor combination!

94. What really irritates you when other people do it, but you do it occasionally as well?

We are all hypocrites at times, but the real trick is to be aware of what we are doing. That requires some self-awareness, and it’s always useful to know if the person you’re speaking with has it.

95. Where have you been?

Who doesn’t enjoy a good travel tale? And who knows, you might have been to some of the same places, but even if you haven’t, it’s fun to talk about where you’ve both been.

96. What is your favorite obscure website?

Because they may not visit many obscure websites, this one is a bit hit-or-miss. But if they do have a favorite, you now have a fantastic site to check out.

97. Have you witnessed or heard of any random acts of extreme kindness?

It’s preferable for the conversation if they can discuss something they’ve seen or experienced firsthand, as this always leads to better stories. If they can’t come up with anything off the top of their heads, there are always feel-good news stories about random acts of kindness. You might even be able to shift the topic to nice things they’ve done for others.

98. What is the most practical skill you’ve ever acquired?

This one appeals to me because you never know what they’ll come up with. And it can actually tell you a little bit about their world and what skill sets they have.

Like most hypotheticals, the more creative you are with your answers, the better. The fun part is imagining what that trend will lead to once it has spread throughout the world.

100. When was the last time you saw or heard something so stupid that you thought it was a joke?

You know the scenario: someone says or suggests something, and you laugh and laugh, convinced that it’s a joke. But then they start looking at you strangely, and you realize they weren’t joking.

Good Questions to Get to Know a Guy

This list of good questions to ask to get to know a guy is exactly what you need! Look no further if you’re looking for great questions to ask a guy. Begin with the basics. These conversation starters are ideal for meeting new people.

Even if you know nothing about the other person, these simple questions to ask to get to know a guy can spark a more in-depth conversation. Here are some questions to start a conversation with a guy:

1. Do you believe fish ever get thirsty?

This intriguing question, which is both amusing and deceptively simple, forces you to imagine yourself as a member of a completely different species. It also makes you consider how we perceive water, thirst, and our surroundings. Furthermore, it is a conversation topic that can lead to an odd but entertaining discussion.

2. What is your favorite movie of all time?

This is an excellent question for a classic conversation starter that can lead to hours of discussion. Sell him on your favorite movie, but keep an open mind when he explains why. This is a good way to learn what he looks for in a movie that he considers to be good.

3. If you could learn more about one subject, what would it be?

When they say that knowledge is power, it might be a good idea to have more of it. This is a great question for getting a glimpse into his deepest desires. It allows the guy to talk about his favorite subject, and you might even learn a thing or two.

4. What do you think is the coolest hobby out there?

This is another excellent question that will help you understand what he is all about. You’ll have a good idea of what he likes to do once he shares his favorite hobby with you. You’ll have plenty to talk about, whether he’s into woodworking or competitive dog grooming.

5. What would you like to make with your own hands?

It’s no secret that men enjoy working on projects. What would he like to make if he had all of the necessary tools and materials? Make this a flirtatious question and follow it up with a challenge. Ask him what he would make for you if he had no constraints. Discover what kind of object he’ll create for you.

6. Who is your favorite athlete, past or present?

Even if he isn’t a sports fan, almost everyone has a favorite athlete. This chance question will spark a discussion about who he admires. Athletes are known for their incredible discipline and dedication, so find out who he idolizes. That way, you’ll learn more about him.

7. If you could change one movie ending forever, what would it be?

We’d all like to give a movie our own spin. Give your guy friend the opportunity to play M. Night Shyamalan for a few minutes to see how creative he is. In order to get him to talk about it seriously, ask him interesting follow-up questions.

8. When and where did you grow up?

It’s a simple conversation starter, but it opens the door to a world of possibilities. He’ll tell you about his family, which will reveal how he was as a child. It’s important to know because his family is the longest-lasting relationship he’s ever had.

9. Where is your favorite place you’ve ever visited?

A person’s favorite vacation spot reveals a lot about their interests and worldview, in addition to opening up many topics for discussion. To keep the conversation going, ask them what their favorite food from that particular location was.

10. What is your sport?

Although not everyone is a sports enthusiast or fan, many people can respond to a common topic. Sports are a great way for guys to bond, whether he’s an athlete or a fan. At the very least, you can argue why yours is superior.

11. If you could train with any athlete, who would it be?

This question is similar to asking about his favorite athlete, but it opens the door to a discussion about why the chosen athlete would be the best choice for a personal trainer. You could also offer your thoughts on the matter and list the factors that led you to select that particular athlete.

12. Who do you believe is the most interesting person alive today?

Every day, we read about incredible people who are leaving their imprint on the world. People are constantly broadening their horizons, whether in science, technology, or content creation. Perhaps one of them has a dream job. Which one fascinates him the most, and why?

13. What would you keep if you could only keep one non-sentimental possession?

Intimate questions like this one help you understand what activities or possessions are most important to him in his life. It’s a deep question to answer because the item must be non-sentimental. Few people are able to separate themselves from the sentimental value of an object, especially one that they want to keep.

14. What would you do if the world stopped moving for an afternoon and only you could move, and no one could see you or remember what you did?

These deep questions to get to know a guy leave a lot of room for interpretation. Find out what illegal or crazy things he wants to do and see if you agree with them. But don’t dismiss him too quickly. Keep in mind that this is all hypothetical. Otherwise, it could be your greatest regret.

15. If you could eliminate one product from the market forever, what would it be?

Things that have been invented but do not serve a significant purpose are sometimes a person’s biggest pet peeve. We’ve all wondered why and how some products exist. What is the ugliest of the ugliest?

16. What is the first thing you would want to know if you went into a coma and awoke in the year 2120?

What begins as small talk will turn into hours of conversation. This conversation is entertaining to think about, but it also forces you to consider what is most important to you right now. If being hooked up to hospital machines that keep him alive is his greatest fear, he’ll tell you all about it if you ask this question.

17. What is something that is fine in small quantities but terrifying in large quantities?

What makes your skin crawl as the figures rise? Don’t be afraid to experiment with this one. If you’re planning a surprise party for your boyfriend outside, it’s probably a good idea to find out what insects or bugs he’s afraid of. That is most likely what he will be concerned about if they arrive in large numbers.

18. If you could go back in time and capture one person and bring them to the present, who would it be and why?

My favorite aspect of these deep questions to get to know a guy is that there can be a million different answers to a single question. This conversation starter can spark a lengthy debate about history, morality, and the implications and paradoxes of changing the past.

19. What is the best/worst food you’ve ever eaten?

Everyone consumes food. This cute question is appropriate for complete strangers as well as new friends. It will undoubtedly get people talking. As a result, make sure to ask really intriguing follow-up questions. You’ll be glad you asked because he’ll have some amusing stories to tell.

20. What would be your favorite ride if you could shrink or grow any animal to the size of a horse?

This is a great conversation starter, whether he wants to fly a bee or go duck back riding. Furthermore, if he enjoys horses, your response to this question will be the funniest thing he’s ever heard. It’s strange and amusing, but questions like this can lift one’s spirits.

21. What Sport Would You Compete In If You Could Be An Olympic Athlete?

Most guys have fantasized about competing in the Olympics at some point in their lives. Furthermore, if he wants to be the most popular celebrity crush among women, he should participate in a common sport. However, as a girlfriend, you would face stiff competition.

22. What do you consider to be the greatest invention of all time?

And why is that? These deep questions to get to know a guy has the potential to spark either a silly or intelligent debate. It will also reveal what he values the most. You’ll discover which items in his home provide him with the most convenience and comfort. It can serve as a guide for you in the future when you give him gifts.

23. If you had to choose between giving up alcohol and giving up coffee, which would you choose?

What is your weakness? No, water is not an option. If he’s a workaholic, he must be the guy who drinks 3 to 4 cups of coffee in order to stay awake until 4 a.m. Alcohol is also required for celebrations or get-togethers. To summarize, giving up one would be extremely difficult.

24. What are you capable of doing today that you couldn’t do a year ago?

These deep questions to get to know a guy may necessitate some deliberation and self-reflection. It also makes it easier for both of you to relate to changes in the world. It could be something he couldn’t do with his previous relationship but now wants to do with you. This could spark a deep discussion, so be prepared to listen.

25. If You Were Confined in Solitary for Six Months, What Would You Do to Stay Sane?

Where do you find peace? This question elicits information about what makes him tick. This would be a difficult question to answer. Being alone for three days with nothing to do is insane. What if it increased by 60 times? Prepare to hear and take notes on what he has in mind. I mean, just in case.


You’re now fully prepared with the best deep questions to get to know a guy. When you don’t have the right deep questions to ask a guy, it can be difficult to start a fun conversation with him. So, hopefully, these questions to ask will help you start interesting conversations with the guy you like. The best thing to do here is to anticipate the questions that will elicit a response from your guy. Then, use those get to know you questions to find out who he truly is.

Frequently Asked Questions

What should I ask a guy to get to know him over text?

What is your all-time favorite film?
What do you usually do on weekends?
What is the most important lesson you’ve ever learned?
What was the most embarrassing thing you ever said or did in front of someone you cared about?
What was the most recent concert you attended?…

What are some personal questions to ask a guy?

What has been your proudest achievement in life so far?
What has been your lowest point in life?
What causes you to become emotional?
What causes you to be stressed?
Do you have faith in a higher power?
Would you want to know the date of your death if you had the ability to do so?

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