Here is a great set of unique questions to ask a guy. They are designed to get an interesting conversation started, and so some of the questions are a bit off the beaten track.
Remember every guy is different, so pick and choose which questions you think will work best for your guy or pick questions that you really want to know the answers to.
Sometimes you’ll be surprised at which questions a guy will find interesting. So even if a question seems like something he wouldn’t be interested in, it might be worth a shot.
Before we start, remember to ask lots of follow up questions to find out more and to keep the conversation going. And if you’d like an image or PDF of the first 50 questions without commentary, scroll down to the bottom we’ve got both waiting for you.
List of questions to ask a guy
These first 50 questions have a bit of commentary and are what I consider to be the most interesting questions.
There is a list of 150 more questions to ask a guy at the bottom of the page without commentary that are still really good. If you can’t find what you are looking for in the top 50 questions you’ll find it in the list at the bottom of the page! So without further delay, here are some quality questions to ask a guy!
1. What was your best drop the mic moment?
Who doesn’t like telling an awesome story about themselves? This will give your guy a chance to tell you a good story and is a great way to get him talking. It will also let you know what kinds of things he is into and what he considers important.
2. If you could learn only one magic spell, but it could only do something mundane and boring, what would the spell do?
A fun question that can lead to some really creative answers. Some examples might be: unclog a drain, make toast slightly more brown, unjam a copier, etc. You could further the conversation by trying to think of the incantation that would go with the spell.
3. You wake up suddenly in the middle of the night. What would be the scariest sound to hear after waking up?
It’s great because it might give you some insight into what he is afraid of. Either that, or you’ll give him a chance to make you laugh if he want’s to make it into a joke. Either way, it’s a fun question to ask a guy and one that makes follow up questions easy. You can talk about amping up scariness of the situation, talk about his other fears, or perhaps try to find fears you have in common.
4. What high level job do you think you could lie your way into with no experience and no one would notice?
This question has a lot of possible answers, but to really make it fun, talk about how he would be able to stop people finding out he was fraud. Sure it sounds like the plot for a bad comedy movie, but still, it’s a fun question to answer.
5. Who or what is your nemesis?
We all have things or people that we absolutely hate. I’m sure he does too. And since everyone loves talking about what annoys them, well, this is a great question to get a conversation going. If you want to, you can encourage funny or silly answers; like jars that don’t open or YouTube videos that load ads perfectly but not the video. You can easily move the conversation to a lighter rant about generally annoying things.
6. What would be the consequences of a scientific discovery that extended the life span of humans to 500 years?
You two can skip this one if you aren’t in the mood for a serious discussion, but I think you’d be surprised at how many guys will really get into answering a question like this. You can discuss how societal norms might change, or how it would affect the progress of technology. There really are a lot of directions you can take this question.
7. What’s the worst and best thing about being male?
How much do you know about what it’s like being a guy? Well now is your chance to find out more. I think you’ll be surprised at some of the answers the guy you are talking with will give. You might also try moving the conversation to talking about some small annoying things about being a guy. This question is really great because it’s a lot of fun to answer and you’ll probably find out some things you didn’t know.
8. What childish thing do you still enjoy?
We all have things that we carry over from our childhood and I’m sure he does too. He might not admit it but he probably still likes peeing in the snow and building sand castles. This question is likely to get you some cute answers. Remember you don’t have to limit it to just one childish thing, you can get him to list off more.
9. What movie can you watch over and over and never get tired of?
He’ll definitely like telling you about his favorite movie, and more importantly you’ll learn what types of movies / shows he likes. This question is easy to expand upon because you can start talking about favorite movies and TV shows, as well as movies or shows you hate.
10. What long shot have you taken that really paid off?
He’s probably never been asked this question before, so be ready to give him some time to think. You’ll probably get an interesting answer though, either a story or a fact that you didn’t know about him.
11. If you designed and built a tree house, what would it look like and what would be in it?
This one is probably my favorite in this list of questions to ask a guy. It’s pure creativity gold. It’s great because every guy secretly wants a bad ass tree house get away for themselves. I don’t know what it is, but I’ve never met a guy who hated tree houses.
All guys dream of tree houses that have bridges and rooms and drop down ladders. There is a reason so many men want to build tree houses for their kids. It’s not for the kids, it’s for the dad.
12. What movie do you wish life was more like?
Another question that is fun to answer and gets a really unique conversation going. Just remember to talk about the small things that would change as well. Really dive into how everyday life would change if it was more like the movie he choose. Don’t be afraid to take it to a ridiculous level.
13. What is the most interesting piece of trivia you know?
He gets to show off some of the things he knows, and you get to learn some new stuff. Try and get him to tell you something you don’t know. It’s a win win.
14. Which celebrity would make the worst leader of a country?
What really makes this question fun is imagining what the celebrity would do once they were leader and what kinds of laws they would make. This one is always great for a laugh. To keep the conversation going, keep switching out the celebrity.
15. What were you really into when you were younger but now think is silly?
Find out what embarrassing things he was into when he was a kid. Great ammo for some good natured teasing later on.
16. What is the most useless thing you know how to do?
What kind of hidden talents does he have? This is always great because usually he can show you. We all have silly and useless talents, now you can learn about his!
17. How many phones have you broken or lost?
A seemingly simple question that sometimes can lead to a really long discussion. That’s because usually behind every broken or lost phone there is a story. Either that or he is just super clumsy or forgetful, which is also good to know.
18. Which historical figure wasn’t as amazing as most people think they were?
I know not everyone is into history. But even if he has only a passing interest in history, he’ll probably like this question. After all, like they say, “Great men are seldom good men”.
Plus you might learn something you didn’t know about a famous historical figure. Or you could skip this one if you both couldn’t care less about history. If you do decide to go for this one, be sure to do a bit of research and find one if you don’t already have one in mind.
19. You are in charge of making insects a popular food item. You have 1 billion US dollars to achieve your goal. How do you do it?
Here is another creative one. You can see how quickly he can think on his feet and how creative he is at solving problems. Sure it’s a bit of a random question, but it’s a fun way to talk through some creative ideas. Plus, solving a problem together is a great way to have a conversation that doesn’t feel forced.
20. What is the highest pressure situation you have experienced and how did you handle it?
Similar to the drop the mic moment question, this one will give him a chance to tell you about a story that is important to him. Just know that there will probably be some exaggeration and embellishment happening when he tells you the story, even if he doesn’t mean to. Memory is a severely flawed thing after all!
21. What’s something you were really stressed about, it turned out to be no big deal?
A fun question to answer, but also very informative. You can find out what types of things stress him out and you can also see how high strung or laid back he is. Plus it’s another chance for a story, and almost everyone likes telling stories about themselves.
22. What are you tired of hearing about?
With a 24 hour news cycle there’s always some news story or phenomenon that’s past its interest expiration date. Ask him this question and you can see what types of things he doesn’t have patience for and it will also let you know what topics to avoid in conversation.
23. What three events made the biggest impact on who you are today?
One of the best questions you can ask a guy. It will let you know a little bit more about his past, how he views himself, and what he considers important. Plus it’s fantastic because there are endless follow up questions you can ask about these cornerstone events in his life.
24. What is something that most people get wrong?
Lots of different answers to this one, so it’s pretty hard to guess what kind of answer he’ll come up with. But it’s a great little question to get a conversation going or at least come up with some complaints you can both commiserate about.
25. What’s the biggest doubt you have?
We all have doubts. Whether those doubts are about the world at large or ourselves. This one can really lead to a serious conversation but sharing doubts can be an excellent way of creating a strong bond between two people.
26. What would you NOT do for 5 million dollars?
This is a fun one to answer. And it can tell you a lot about the guy as well. You can find out what morals he considers to be most important and what activities he finds detestable.
27. What do you think you know a lot about but probably don’t?
Everyone likes to think they are experts at lots of things. But let’s be honest, we are actually average or below average at most things. Just think about how many people will say they are an above average driver. A little self introspection is always a good thing.
28. What is society doing now that in 20 years will be laughed at and ridiculed?
Just think back 20 years and you’ll find plenty to laugh about. And that’s how it’ll be 20 years from now. People will be laughing and ridiculing lots of things that are popular now. So what do you think “future you” will look back on with disdain?
29. What double standard is ridiculous and needs to be ended?
Lots of double standards to choose from. So now it’s time to find out what issues he thinks are important or whether he isn’t really into societal issues.
30. What’s your worst customer service story, either as the customer or as the employee?
He probably has a couple. And who doesn’t like a good customer service gone wrong story? If he’s worked in a customer service field, he’ll definitely have a few. And if he hasn’t, he probably has some customer service horror stories from the customer side of things.
31. Who has completely lost your respect?
A great question for seeing what values he thinks are important. Also a great conversation starter as there are more than few celebrities that have fallen from grace.
32. What’s the most effective way for a government to control its people?
Okay, so I debated whether or not to put this one into the list. It’s a little more deep and serious than most of the other questions. So feel free to throw it out if it’s not appropriate. But it definitely can lead to some very interesting conversations if either of you are at all interested in politics or history. But if you really like this question you might try our deep conversation topics or deep questions to ask a guy.
33. If you had to choose one cause to dedicate your life to, what would that cause be?
We all have causes that we hold dear. Now you’ll be able to find out what his is. You’ll also find out how active he is in charity or volunteering. But besides all that useful information, it’s still a fun question to answer because it really puts what we are doing in daily life into contrast with what we want to be.
34. If you died today, what would your greatest achievement be?
A great introspective question that everyone, including you, should ask themselves. It’s easy to get lost in the day to day and forget that we’ll eventually die. It’s important to be reminded that life is supposed to be lived.
35. What have you done to make the world a better place to live in?
This one may or may not have the same answer as question 34 and is probably related to question 33. All in all though, it’s a great question to ask to find out some of the things he’s done and the things that he thinks are important.
36. Who are some people you only met once but they left a big impression on you?
Like the saying goes, you are the same person you were five years ago except for the places you’ve gone, the books you’ve read, and the people you’ve met. So who has he met that changed his outlook on life?
37. What do you think is the most common complaint people in your country have?
Basically an open door to a political discussion. Which can be good or bad depending on what you are after. So make sure to use this question with caution!
38. What one question can you ask someone to find out the most about them?
A question that is great on a lot of levels. It requires some thought to answer but can lead to some great conversations. He’ll come up with a question that you can both answer and you can come up with your own question as well. You’ll both learn a lot more about each other.
39. What is your closest close call?
This one is mostly to get him to tell a good story. But it can sometimes dig up some emotional memories so use this question with caution. Still, it’s great for getting to know more about him.
40. What stories from your life will you tell your children about (assuming you have children)?
Here is another great one because it can lead to some really great stories that he’ll enjoy telling and hopefully you’ll enjoy listening to.
41. If you could become the number one expert in one niche field, what would it be?
Perfect for finding out more about his interests and perhaps even some of his goals. Who knows, you both might share an interest in the same thing or you might have never heard about it. Either way it’ll give you both a lot to talk about!
42. What was the worst purchase you’ve ever made?
Kind of a random question but it can lead to some really interesting answers. Plus at the very least you’ll learn about something you shouldn’t spend money on!
43. What did you think was silly until you tried it?
I’m sure your familiar with green eggs and ham. Well now you can find out his green eggs and ham moment. We’ve all been in the situation where something we thought was stupid turned out to be amazing. And who knows you might even get to try something new and amazing!
44. Who is your favorite author?
Okay this question is a bit generic but it allows you to find out how much he is into reading and what kinds of genres of books he’s into. If he isn’t into book or doesn’t have a favorite author that’s also great to know!
45. When you are day dreaming, what do you dream about?
What goes on in his head when his eyes glaze over? Well now it’s time to find out!
46. What do you believe even though you know it’s probably wrong?
Sure it’s a little similar to the doubts question but it can lead to some really interesting answers. The answers can get a bit serious and dark but I really do think this is a great question. It’s a question that everyone should occasionally think about. We should always be questioning our beliefs and trying to find truth even if it can be a bit uncomfortable.
47. What signs make you think someone will go on to be successful?
This seems like a simple and straight forward question, but it actually tells you a lot about what traits he values in other people. And it can also tell you a lot about what he thinks success is.
48. What’s the most unusual but fun experience you’ve had?
A great question to as a guy. Why? Because as a guy I can tell you we do some incredibly dumb and unusual things in the name of a good time.
49. What was the weirdest habit you had as a child?
All kids are weird in their own way. He was weird too when he was kid. So now you can find out some embarrassing and probably funny things about his childhood.
50. What is the most irritating food?
Yeah this one is a little bit of an odd one to go out on. But I like it. And it’ll probably lead to some funny answers.
150 Extra questions to ask a guy
- If you could level up in life just like in video games, where would you put your next skill point?
- What have you done wrong for most of your life and only recently found out the right way to do it?
- How does your definition of a “real man” differ from the mainstream stereotype of a “real man”?
- What video game do you wish life was more like?
- What’s the best prank you can play on someone?
- If time wasn’t an issue and you had forever to master a skill, what skill would you master?
- What was the biggest mistake in history?
- What are some fun euphemisms for everyday activities?
- If you wanted to give a tourist the local flavor of where you live, what would you have them do?
- What does friendship mean to you?
- What would be the worst thing to have a phobia of?
- Who or what do you always have time for?
- What are two things you’ll never spend money on?
- If you could make everyone in the world believe one thing (regardless of whether it’s true or not), what thing would you choose?
- What do you need to rant about or get off your chest?
- What’s the best bad decision you’ve made?
- What could you give a two-hour impromptu lecture on?
- What can a movie do to make you get up and walk out?
- What are you so incredibly terrible at, that you’ve given up ever doing it again?
- What was your favorite cartoon when you were growing up?
- What are some things people have selflessly done to make your life better?
- What do you own that a lot of people comment on?
- What’s your perfect burger?
- Which fictional villain is your favorite?
- You’re given $300,000 to make one room in your house or apartment ridiculously amazing, what room do you pick and what upgrades do you make?
- Have you ever seen anyone pull the “Do you know who I am?!” card?
- What are some boring games or sports and how can they be livened up?
- What game do you always lose?
- What do you like to do that is traditionally considered feminine?
- What’s the weirdest thing you used to eat as a child?
- What was the last movie that made you cry?
- What small stuff do you always sweat?
- If you could add 4 hours to your day, what would you spend that 4 hours doing?
- What’s something everyone should experience at least once in their life?
- What state / city would like to move to?
- What’s your earliest memory?
- What do you think is the most confusing idiom for people learning English?
- What are some websites you used to use all the time but have stopped using?
- Who would be the worst celebrity to have dinner with?
- What’s something obvious that you never noticed until someone pointed it out?
- What small thing makes you angrier than it should?
- What one thing would you most want to save if your house caught fire? Assuming that any people or animals made it out safely already.
- What flavor combination is kind of weird but you really like it?
- What really annoys you when other people do it, but you occasionally do it as well?
- Where have you traveled?
- What obscure website do you absolutely love?
- What random acts of extreme kindness would you like to see?
- What’s the most useful skill you’ve ever learned?
- If you were given the ability to make one new trend and it be instantly popular, what trend would you create?
- When was the last time you remember someone doing or saying something so stupid that you were sure it was a joke?
- What was the most historic thing you witnessed in person or took part in?
- What do you know way too much about?
- If it was decided that all countries would be abolished and the entire earth would be one unified political body, what would be the capital city of Earth? What would its flag and anthem be?
- What’s the best $5 you’ve ever spent?
- What movie really encapsulates the era it was made it?
- What fictional character is portrayed as a hero but is actually more like a villain?
- What was a random compliment that someone gave you that really stuck in your memory?
- If you could go back in time and inspire someone to make a present-day invention, what invention in what time period would advance humanity the most?
- What’s your phone or computer wallpaper?
- What’s your favorite board or card game? How about your least favorite?
- What was the worst thing you ever tasted?
- If you were a ghost, how would you haunt?
- What’s one small thing you could do each day that would greatly improve your life?
- What makes you special and unique?
- What do you judge people for that you probably shouldn’t?
- What movie quote are you tired of hearing?
- What would be the last movie you’d like to see before you die?
- What two things are you most passionate about?
- What must be seen or experienced in person to really appreciate it?
- What common ingredient or spice do you despise?
- What celebrities are most likely to be jerks?
- How well can you explain how a car works?
- What’s the first thing that you think when see a homeless person?
- What’s the most ridiculous tattoo you’ve ever seen?
- If you were an actor, what kind of roles do you think you would be good at?
- What’s the most paranormal thing that has happened to you?
- What movie would be better if the plot happened in reverse?
- What’s currently legal but won’t be in ten or twenty years?
- What would you like to be the best in the world at doing?
- What have you done a lot but are still incredibly bad at?
- What are you too old for but still enjoy?
- What was fun to do once, but you’ll never do it again?
- If you could pick up any one instrument and instantly be a virtuoso at it, what instrument would you choose?
- What’s your best one liner?
- What was the last major goal you accomplished?
- What are some problems you realize are first world problems but are annoyed by them anyway?
- What do you collect?
- What’s the worst injury you’ve ever gotten?
- Would you volunteer to go colonize another planet if it meant you would never return to earth?
- What would be the worst store to have a $1,000 gift card for?
- When was the last time a stranger made your day?
- What’s something you’re surprised no one has figured out how to do yet?
- What’s your creative outlet?
- When was the last time that things got a little too real?
- What do people idealize but really shouldn’t?
- Who’s famous for their talent, but really shouldn’t be?
- If you could add one rule that everyone must follow when they use the internet, what would your rule be?
- What’s worse than you thought it would be?
- What have you really wanted to do for a long time but haven’t done yet?
- What’s the worst slip of tongue you have heard about?
- What activity or hobby is so filled with hateful people that it puts you off trying it?
- What’s your “back in my day, we…”?
- Who is the funniest actor or actress still doing movies or TV shows?
- What’s the best part of your day?
- What’s the strangest hobby you’ve heard of?
- What language do you like the sound of even though you don’t know how to speak it?
- What’s your favorite movie from each genre?
- What’s your definition of a good human being?
- What news headline would you most like to see?
- If you could run away from it all and start fresh somewhere new, would you?
- If you were given $10,000 to throw an amazing party, gathering, or event, what would that look like?
- When was the last time you felt completely out of the loop?
- What are some small pleasures that make you way happier than they should?
- What’s something you boycott but don’t make a big deal of boycotting?
- What social media post has really stuck with you?
- What common piece of advice or words of wisdom don’t actually make much sense?
- If you had to be stuck at one age forever, what age would you choose?
- What’s an example of a modern masterpiece?
- What useless bit of information have you memorized and will probably never forget?
- What quote has always stuck with you?
- What’s the weirdest thing you’ve seen while driving?
- What would be the worst animal to be eaten by?
- On a scale of existential crisis to living the dream how’s life going?
- Besides religion and politics, what topic always gets heated in your circle of friends and acquaintances?
- If you could show everyone in the world one image for 10 seconds but it couldn’t contain text, what image would you choose?
- What looks like it should taste better than it does?
- If there were an Olympics for average people, what would some of the events be?
- What would an exact opposite of you be like?
- Would you travel to a foreign country all by yourself?
- If States could date, who would be into who and why?
- What’s something commonly done that if you explained it to someone outside of your culture would sound completely insane or at a least a really bad idea?
- What would you recommend to someone if they had the day off and didn’t know what to do?
- What do you imagine the lives of super rich people are like?
- What’s the biggest “scene” you’ve seen someone make in public?
- What fictional character did you / do you have the hots for?
- What’s your best podcast recommendation?
- What happens more often than you’d like?
- What genetic modification would you most like to have?
- What was something you loved but it never really took off or was ended before it’s time?
- Who would you want to play you in a movie about your life?
- What would be the absolute best pet to have?
- What’s a piece of advice that you wish everyone would take to heart?
- What’s one thing your learned this week?
- What’s the dumbest rule you’ve been forced to follow?
- What’s the most absurd thing that has become reality for you?
- Do you think your childhood was better or worse than other people growing up in a similar place and time?
- What’s your most common first thought when you wake up?
- If you had a disease named after you, what would be the symptoms?
- What rules do you make for yourself?
- What’s one regret you have?
- What’s the single most important thing you have done in your life?
Image: Questions to ask a guy
PDF: Questions to ask a guy
Perhaps you’d prefer a PDF version instead of an image? Here you go! An easily printable PDF version of the first 50 questions to ask a guy.
Well those are all of our questions to ask a guy. But we’ve got a lot of questions on the site so there are a lot more questions to ask a guy to choose from!
We’ve got a lot more questions to ask a guy…
Fun questions to ask a guy – A great list of truly fun questions to ask and answer. These questions are great for casual conversations where you are looking to get a laugh.
Interesting questions to ask a guy – Looking for questions that are a little more thought provoking and unique? This is the list for you. Interesting questions that are still relatively casual.
Personal questions to ask a guy – Time to get personal and find out more about him. Use these questions to find out what makes him the person he is.
Random questions to ask a guy – These questions are often wacky and off the wall. Choose wisely because some are quite silly.
Weird questions to ask a guy – Yup, these questions will probably get you a strange look from the guy you are asking. But hey, why not?