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.
After you’ve checked out this list of 200 questions, if you still want more, we’ve got you covered:
- Personal questions to ask a guy
- Deep questions to ask a guy
- Random questions to ask a guy
- Fun questions to ask a guy
- Interesting questions to ask a guy
- Weird questions to ask a guy
Before we start, remember to ask lots of open-ended follow up questions to find out more and to keep the conversation going. And if you’d like an image or PDF of some of the questions without commentary, scroll down to the bottom we’ve got both waiting for you.
200 questions to ask a guy
Without further delay, here are 200 questions to ask a guy!
1. What was your best drop the mic moment?
Who doesn’t like telling an awesomestory about themselves? This will give your guy a chance to tell youa 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. 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.
3. 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.
4. 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.
5. What movie do you wish life was more like?
Another question that is fun to answerand 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.
6. 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.
7. 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.
8. 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!
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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 andone 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.
15. 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.
16. 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, butI 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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”.
23. 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.
24. 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!
25. 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.
26. 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.
27. 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.
28. 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.
29. 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?
30. 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.
31. 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.
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.
51. What video game do you wish life was more like?
This is a great one if the guy is into video games, not somuch if they aren’t. If they are though, make sure to ask them lots of detailsof why they like the game so much.
52. What’s the best prank you can play on someone?
This one can be good to see if the guy is a prankster, andif so, what kind of pranks he finds funny.
53. What was the biggest mistake in history?
If he is into history, awesome, he’ll probably ponder a bitand then give you an answer. And even if he isn’t into history, he’ll probablybe able to come up with a pretty good answer.
54. What does friendship mean to you?
This one can be a bit deep, especially if you are justtrying to be friends with him, so feel free to pass it by if you are trying tokeep things more casual. But it can be a great question to find out howimportant friendship is to him.
55. What would be the worst thing to have a phobia of?
There are so many phobias out there. Here is a list of phobias incase you want to have a look. So many.
56. Who or whatdo you always have time for?
It might be a relative or a friend, or it might be a hobby,or something else entirely. Whoever or whatever it is, it or they are probablyvery important to him.
57. What are two things you’ll never spend money on?
There are all kinds of answers to this one, and his answerscan tell you a lot about his personality or at least his view of the world.
58. What do you need to rant about or get off your chest?
We all need to go off on a rant sometimes. Why not give himthe chance to vent?
59. What’s the best bad decision you’ve made?
I’m sure he’s made a few bad decisions that he wouldn’t takeback. Time to find out what those bad decisions were, because there is usuallya good story behind them.
60. What could you give a thirty-minute impromptu lecture on?
Whatever topic he chooses, he’s probably an expert in it andhas spent a lot of time on it.
61. What can a movie do to make you get up and walk out?
What’s the line that needs to be crossed? Is it a slow buildof cheesiness? Perhaps something offensive or gross?
62. What was your favorite cartoon when you were growing up?
Who doesn’t like talking about favorite things from theirchildhood? Everybody likes to reminisce sometimes, and chances are that he willtoo.
63. What are some things people have selflessly done to make your lifebetter?
This question is great for getting at how grateful he is forwhat others have done in his life. And if he doesn’t think that anyone has selflesslydone anything for him, he has either had a REALLY rough life or he doesn’tappreciate things that people do for him.
64. What are some fun euphemisms for everyday activities?
This question can be a lot of fun if you are both creativewith it. Humans have a ton of euphemisms for all sorts of things, now it’s timeto make some new ones!
65. What do you own that a lot of people comment on?
Maybe it’s a car, a watch, a shirt, or something elseentirely. Whatever it is, he probably has a few stories about the item or thepeople who comment on it.
66. If you could level up in life just like in video games, where would youput your next skill point?
So many to choose from! Strength, intelligence, dexterity,constitution, charisma, or perhaps he would choose to level up a skill he has.This can be a fun question, but its mileage may vary depending on his level ofgeekiness.
67. What have you done wrong for most of your life and only recently foundout the right way to do it?
This question can be good for a laugh. The funniest storiesare when they learned how to do something the wrong way in childhood and didn’tlearn the right way until WAY late in life.
68. How does your definition of a “real man” differ from the mainstreamstereotype of a “real man”?
This question can be quite revealing because it gets at thespecific values that he thinks are worthwhile. It will tell you a lot about howhe views the world and his place in it.
69. What’s your perfect burger?
Definitely an American type of question and mostly just forfun. But it will let you know a little more about what he likes and doesn’tlike.
70. Which fictional villain is your favorite?
You could also follow this up with a favorite hero, but it’susually more interesting to hear about which villain he likes. It could bebecause he thinks the villain had a point or he might just think the villainlooks cool.
71. You’re given up to $300,000 to make one room in your house or apartmentridiculously amazing, what room do you pick and what upgrades do you make?
A great question for pulling out some creativity and findingout what his ideal space would look like. Also great for finding out what kindsof things he wants or at least thinks he wants.
72. Have you ever seen anyone pull the “Do you know who I am?!” card?
Sure, you see it a lot in movies, but does it happen in reallife? Maybe they, or even you have seen it in real life. And I’m sure it wouldmake an excellent story to talk about.
73. What are some boring games or sports, and how can they be livened up?
This one is a lot of fun to brainstorm rule additions and edits together. For example, golf, but there is only one ball, and all the players have to fight over it while they try to hit it in the hole.
74. What game do you always lose at?
Whether it’s sports or video games, guys play a lot ofgames. Now you can find out some games that he is the worst at.
75. What do you like to do that is traditionally considered feminine?
Gender roles and identities are changing. And this questionis a good round-about way to find out his views on masculinity and gender ingeneral.
76. What’s the weirdest thing you used to eat as a child?
Kids eat weird stuff. I did. You probably did too. And heprobably did too. Time to have a laugh at some of your childhood weirdness.
77. If time wasn’t an issue and you had forever to master a skill, whatskill would you master?
A great question for finding out more about his interestsand what he would like to do/be.
78. If you wanted to give a tourist the local flavor of where you are from,what would you have them do?
This one can be a lot of fun, and it works whether you areboth from the same place or different places. It’ll let you or know what it waslike growing up where he did or if you are from the same place, you can havefun brainstorming together and maybe getting some good ideas for things tocheck out.
79. If you could make everyone in the world believe one thing (regardlessof whether it’s true or not), what thing would you choose?
Another one that is great for stretching creativity. Andfeel free to think of more than one thing to make it a bit longer of adiscussion. This question can lead to some very unexpected conversations.
80. What are you so incredibly terrible at, that you’ve given up ever doingit again?
It can be endearing to hear and talk about failures, andthis question is great at pulling out failures without being too negative aboutit.
81. What was the last movie that made you cry?
This question might give you a rough estimate of howsensitive he is. Or at least how often he cries at movies.
82. What small stuff do you always sweat?
No matter how much we try, there are always small thingsthat maybe we don’t need to worry about, but we still do.
83. If you could add 4 hours to your day, what would you spend that 4 hoursdoing?
Chances are, whatever he mentions is something he wishes hecould be accomplishing now but just can’t find the time or energy for.
84. What’s something everyone should experience at least once in theirlife?
A good question to get into a conversation about meaningfulexperiences that he has had or that he wishes he could have.
85. What state/city would you like to move to?
Sure, we all love our hometown, and he probably does too.But there might just be a place he would rather be. Whether it’s in his owncountry or some other country.
86. What’s your earliest memory?
Memories are weird slippery things. Most of our memories areflawed, especially the early ones, and some are outright false. But thatdoesn’t mean they can’t be used for a good conversation!
87. What do you think is the most confusing idiom for people learningEnglish?
So, this is kind of a weird one. If you don’t think it willfly, feel free to skip it. An idiom is a saying that takes on a differentmeaning than the literal meaning. For example, he dodged a bullet or she’sbetween a rock and a hard place.
88. What are some websites you used to use all the time but have stoppedusing?
Ah, our personal website graveyards. The ones we used tovisit almost every day but haven’t thought about in years. Perhaps it’sMyspace, Livejournal, or Newgrounds. But whatever the site, he certainly hasone or three. And it’s always fun to reminisce.
89. Who would be the worst celebrity to have dinner with?
This is a play on the old conversation starter “Who inhistory would you most like to have a meal with?”. Sure, it’s a bit negative,but at least this way you’ll find out who his least favorite celebrity is!
90. What’s something obvious that you never noticed until someone pointedit out?
You know, the things that make you feel stupid and say, “Ohyeah, that makes sense.” It’s always great to share embarrassing stories andhave a laugh at our previous selves.
91. What small thing makes you angrier than it should?
This one is good for finding out what his pet peeves are andhow picky he is about things. And it’s always good to know what annoys people.Whether you use that knowledge for good or evil is up to you.
92. 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 possessions do they hold most dear? Make sure to askfollow-up questions to find out why they chose that item and feel free to askwhat the next thing they would be.
93. What flavor combination is kind of weird, but you really like it?
People like a lot of different types of food and he isprobably no exception. And who knows you might just find your new favoriteflavor combination!
94. What really annoys you when other people do it, but you occasionally doit as well?
We can all be hypocrites at times, but the real trick isbeing able to notice that we are doing. That takes some self-awareness, and it’salways good to know if the person you are talking to has that self-awareness.
95. Where have you traveled?
Who doesn’t love a good travel story?! And who knows you mayhave visited some of the same places, but even if you haven’t, it can be goodto chat about the places you’ve both been.
96. What obscure website do you absolutely love?
This one is a bit hit or miss, because they may not visitmany obscure websites. But if they do have a favorite one, well, now you’ve gotan awesome site to check out.
97. What random acts of extreme kindness have you seen or heard about?
It’s better for the conversation if they can talk aboutsomething that they’ve seen or experienced first-hand because that always leadsto better stories. But if they can’t think of anything off the top of theirhead, there are always feel-good news stories about acts of kindness. You mighteven be able to transition the conversation into nice things they’ve done forothers.
98. What’s the most useful skill you’ve ever learned?
I like this one because you never know what they’ll come upwith. And it actually can tell you a bit about what their world is like andwhat skill sets they have.
99. If you were given the ability to make one new trend and it be instantlypopular, what trend would you create?
Like most hypotheticals, this one gets better the morecreative you get with your answers. The fun of it is imagining what that trendwill lead to once it gets out into the world.
100. When was the last time you remember someone doing or saying somethingso stupid that you were sure it was a joke?
You know the situation, someone says something or suggestssomething, and you laugh and laugh, thinking it’s a joke. But then they look atyou all weird and you realize they weren’t joking.
101. What was the most historic thing you witnessed in person or took partin?
A lot of times, people won’t have any answers to this question. But sometimes, just sometimes, you’ll get an amazing story and some insider info on a historical event.
102. What do you know way too much about?
It might be something he is passionate about, or it might besomething he was forced to learn for his job. Either way, he’ll probably beable to answer nearly any question about it. Whether you want to hear about it,well, that’s up to you.
103. If it was decided that all countries would be abolished and the entireearth would be one unified political body, what would be the capital city ofEarth? What would its flag and anthem be?
So, this question is definitely a bit out there. But it canbe a lot of fun if he is creative and enjoys hypothetical questions. If it’s aquestion you think he’ll be interested in, you can both spend timebrainstorming together.
104. What’s the best $5 you’ve ever spent?
Answers to this question are all over the map, you neverreally know what kind of answer you’ll get. But there is a good chance he hasnever been asked this question, so hurray for novelty!
105. What movie really encapsulates the era it was made in?
Basically, what 80’s movie was the most 80’s? What 90’smovie was the most 90’s? This can be a bit hard if you are both young becausethe 2000s got kind of all merged together, but you might be able to salvagesomething from this question even if you are both on the younger side.
106. What fictional character is portrayed as a hero but is actually morelike a villain?
It could be an action hero that goes around destroyingpeople’s property and livelihoods, causing car crashes and general mayhem. Orperhaps a hero whose actions bring about horrible unintended consequences.Either way, it can be fun to think about the traditional hero’s journey in adifferent way.
107. What was a random compliment someone gave you that really stuck inyour memory?
Compliments, people should give more of them. They don’tcost anything, and they make someone feel awesome.
108. If you could go back in time and inspire someone to make a present-dayinvention, what invention in what period would advance humanity the most?
Okay, I know, this is almost like an essay question. But ifhe is into history and innovation, this might just be a killer question.Although, if he isn’t into history and inventions or doesn’t enjoy beingcreative, you might want to give this on a pass.
109. What’s your phone and/or computer wallpaper?
This seems like a weird question, but it can be surprisinglytelling. And most likely, he has reasons why he chose the wallpapers. Whateverit is, even if it’s just the stock wallpaper, it will tell you a little bitabout him.
110. What’s your favorite board or card game? How about your leastfavorite?
With his favorite, he’ll be more than happy to tell youabout it. With the least favorite, there is a good chance that there is somestory behind it. Maybe it’s a family member that always beat him, or it’s justgenerally rage-inducing.
111. What was the worst thing you ever tasted?
This is another question that you never really know whatkind of answer he’ll come up with. But whatever it is, there is probably a goodstory behind it. Probably a gross story, but hey, those can be fun too!
112. If you were a ghost, how would you haunt?
Will he go the traditional routine of chains and moaning, orperhaps throwing stuff around? Maybe he’ll get more playful with his hauntingor perhaps he’ll go with the horrifying approach. This one can be a reallygreat one if you are both into horror movies/shows. And it’s easy to transitioninto a discussion about horror in general or ghost stories.
113. What’s one small thing a person can do each day that greatly improves theirlife?
This question is good on its own but is also good fortransitioning into a conversation about habits in general. Or you couldtransition it into a conversation about self-improvement.
114. What makes you special and unique?
This question is a little more personal. It seeks tounderstand what they think makes up the core of who they are or at least whatsets them apart from others. It might also lead to a dead-end because a lot ofpeople haven’t thought about what makes them unique, so he might not have ananswer for this one.
115. What do you judge people for that you probably shouldn’t?
It’s hard not to judge people, no matter how hard we try.And a lot of time we judge people by things we shouldn’t. Sometimes it’sconscious, but more often it’s unconscious. He may or may not answer this onetruthfully, because to answer it truthfully, well, you have to confront yourown prejudices.
116. What movie quote are you tired of hearing?
There are so many movie quotes that get repeated again andagain, and again. Years after the movie came out. So which ones is he fed upwith?
117. What would be the last movie you’d like to see before you die?
This is kind of an odd one. You may get an interestinganswer or perhaps just a baffled look. It helps if he is really into movies,but feel free to skip this one if you are uncertain about it.
118. What two things are you most passionate about?
A great question for starting a great conversation. Whateverthose two things are, he can probably talk hours about them. And if he can’tthink of things he’s passionate about, well, you can always transition thequestion into “What are some of your favorite things to do?”.
119. What must be seen or experienced in person to really appreciate it?
This is another question that you never know what directionhe’ll take it in. But whatever direction he goes, it’s sure to be somethingthat had a significant, possibly formative effect on him.
120. What common ingredient or spice do you despise?
It’s weird, but most people have at least one ingredient orspice that they just loathe and can’t eat whatever it goes into. For me, it’sthose big bean sprouts. But everyone is different and it’s a good question toask if you plan on asking him out for a meal!
121. What celebrities are most likely to be jerks?
They can’t all be awesome people like Tom Hanks, KeanuReeves, or Jennifer Lawrence. Some celebrities are bound to be jerks. If youcan’t think of any, you could probably Google it find some misbehaved celebrities.Although it’s often more fun to brainstorm and guess.
122. How much of a handyman are you?
You might want to be careful with this question, becausethey might think you are insinuating that they aren’t “manly”. But if they aregood at fixing things, they probably will enjoy talking about it. You’ll justhave to read how you think he’ll take it.
123. What’s the first thing that you think when see a homeless person?
Talk about a loaded question. This will tell you a lot abouthow he views others and how compassionate he is. And if you both don’t have thesame view; it can definitely lead to an argument. So, handle with one withcare.
124. What’s the most ridiculous tattoo you’ve ever seen?
Oh boy howdy are there a bunch of terrible tattoos. Afteryou’ve talked about some, just Google it. There are bound to be some laughs,some cringing, and some complete and utter bafflement.
125. If you were an actor, what kind of roles do you think you would begood at?
Go ahead, typecast yourself! Or at least get him to typecast himself. Would he be an action star, a charming comedian, or perhaps a villain? Maybe just an extra? It can be a lot of fun to imagine what roles you would be picked for if you were an actor.
126. What’s the most paranormal thing that has happened to you?
Whether you believe in the paranormal or not, this can be afun question. Because everyone loves a good ghost story, even if in the end youfind out that there were no ghosts. You probably have a few unexplained storiesas well that you could share.
127. What movie would be better if the plot happened in reverse?
I love this question because it makes you think about moviesin a totally different way. Sometimes it can be hard to think of a good one,but if you run through a couple of movies, you’ll get the hang of it. Justremember to reverse the order of the main plot points that happen and not thespecific details.
128. What’s currently legal but won’t be in ten or twenty years?
To help out with this question, think about what was legaland normal 20 years ago but is now illegal. You’ll get the general gist and beable to think about some examples that will be illegal soon or relatively soon.
129. What would you like to be the best in the world at doing?
It could be anything. It’ll be interesting to hear what hecomes up with. It’s also interesting to see how much time he’ll put intothinking about it. Some people know right away, and some ponder it for ages.
130. What have you done a lot but are still incredibly bad at?
No one can be good at everything, so there are probablyplenty of things that even though he has had a lot of practice, it’s still justnot happening. You’ve probably got a few you can share as well.
131. What are you too old for but still enjoy?
Growing up is overrated. Those who are still children atheart seem to have the most fun. This question is good for getting to know hima little better and growing closer by sharing things that he probably doesn’ttell a lot of people about.
132. What was fun to do once, but you’ll never do it again?
We’ve all had those things that we are glad we did butwouldn’t do again. A lot of times, there is a pretty good story behind it aswell.
133. If you could pick up any one musical instrument and instantly be avirtuoso at it, what instrument would you choose?
This is kind of an off the wall question, but it can be fun.Definitely a question that he probably has never been asked before. Give himtime to think, and make sure to ask why he chose the instrument he did.
134. What’s your best one-liner?
Who doesn’t love a good joke? And even though one-liners areusually pretty cheesy, they can still be fun. And who knows you might even finda one-liner you can use later.
135. What was the last major goal you accomplished?
Great for finding out what he considers a worthwhile goal,and it can easily transition into a conversation about what goals are next onhis list. You might even find out how dedicated he is to achieving his goals.
136. What are some problems you realize are first world problems but areannoyed by them anyway?
Sure, they aren’t really serious, but they can still beannoying. Chances are if he grew up in a prosperous country, he probably hasexperienced some first world problems. I’m sure you have a few too, so why notcommiserate?
137. What do you collect?
You never know what he might like collecting. People collectall kinds of things. I think collecting things might be something fundamentalto human nature. It scratches one of those primordial itches.
138. What’s the worst injury you’ve ever gotten?
We’ve all got injuries. And every injury has a story behindit. Usually, this one is fine, but if he was in a car wreck or somethingsimilar where someone died, it could get a bit dark. Just a heads up.
139. Would you volunteer to go colonize another planet if it meant youwould never return to earth?
Some people love testing boundaries, exploring, and going tothe edge of human experience. And some don’t. No judgment either way but it’sgood to find out where on the spectrum he is. Maybe he’d join the second orthird wave? Or maybe he’s quite happy here on Earth.
140. What would be the worst store to have a $1,000 gift card for?
Everyone loves money. But gift cards can be pretty rough ifthey aren’t for a store you like. Find out what shops he loathes with thisquestion.
141. When was the last time a stranger made your day?
Who doesn’t love a feel-good story? And strangers helpingstrangers is a wonderful example of human goodness. Or it might be somethingfunny a stranger said that made his day. Either way, it can be a fun,lighthearted question.
142. What’s something you’re surprised no one has figured out how to doyet?
You might need to give him some time to ponder this one.It’s not something we think about regularly. Most people will immediately go tocuring the common cold, but he might come out with something a lot moreinteresting.
143. What’s your creative outlet?
This is a fantastic question to get to know him better. Makesure he knows that “creative outlet” can be nearly anything. It doesn’t have tobe something traditional, like painting or playing an instrument. It can beplaying a game, fixing up a car, cooking, social media, or something completelydifferent.
144. When was the last time that things got a little too real?
You never know what he’ll come up with this one. Thingsgetting a little too “real” is pretty subjective, so it kind of depends on how heinterprets the question. It can be a fun one for discussion though, or at leastfor a good story.
145. What do people idealize, but really shouldn’t?
It could be a trend, a celebrity, a value, or somethingtotally different. This one can lead to an in-depth discussion of society. Ifyou aren’t into that or don’t think he would be, you could always give this onea pass.
146. Who’s famous for their talent, but really shouldn’t be?
Similar to the last question but a little more specific.This one is all about celebrities. And with so many celebrities out there, itshould be easy to come up with a few examples.
147. If you could add one rule that everyone must follow when they use theinternet, what would your rule be?
A fun hypothetical that can lead to some entertaining orserious answers. Because let’s face it, the internet is not always the bestplace. It could definitely use some improvement.
148. What’s worse than you thought it would be?
Another question that could have any number of differentanswers depending on his experience. It could be something funny, somethingserious, something personal, or something that happened to society.
149. What have you really wanted to do for a long time but haven’t doneyet?
Sure, it might be a major goal that they’ve been thinkingabout tackling for a long time. But it could also be something small andinsignificant that they just haven’t gotten around to.
150. What’s the worst slip of the tongue you have heard about or that hashappened to you?
Slips of the tongue can be disastrous, hilarious, and/ordeeply embarrassing. But whether you cringe or laugh, it’s sure to be somethingentertaining that you’ll enjoy.
151. What activity or hobby is so filled with hateful people that it putsyou off trying it?
This is kind of a hit or miss question. It all depends onwhether they know about a hobby or activity with a hateful community. But ifthey have played any online multiplayer games, they’ve probably run into atleast one community that is less than friendly.
152. What’s your “back in my day, we…”?
The stereotype is old people saying this, but you’d besurprised how even younger people do this, especially with games or media.People love reminiscing about when they were growing up.
153. Who is the funniest actor or actress still doing movies, TV shows, orYouTube?
If you have heard of the person, you can have a chat aboutsome of their work. Plus, you’ll get to know what their sense of humor is like.If you haven’t heard of them before, it looks like you’ve got some hilariousmaterial to check out, assuming they do your type of humor.
154. What’s the best part of your day?
Sure, you learn about something they like to do, but it’salso a way to point out some of the joys of daily life that we don’t alwaysappreciate. You might even find out after thinking about this question thatthere are parts of your day you love but haven’t really thought about much.
155. What’s the strangest hobby you’ve heard of?
There are so many hobbies out there. So many. And some of them are quite unique. If you or he can’t think of any off the top of your heads, here is a list of hobbies you could check out.
156. What language do you like the sound of, even though you don’t know howto speak it?
This is another good one because so many people havedifferent opinions about what languages sound the best. And then you cantransition into a discussion about which accents sound the best.
157. What are some of your favorite movies from each genre?
This is a great conversation starter for talking aboutmovies that each of you likes. You can also talk about which genres you bothlike as well. You might even get some awesome movie suggestions for genres you aren’tnormally into.
158. What’s your definition of a good human being?
This one can be as deep or as shallow as he wants to makeit. And everyone will have a slightly different take on it. After all, thetopic is one that philosophers have been asking for as long as there have beenphilosophers.
159. What news headline would you most like to see?
This can be an interesting one. Especially if he puts somethought into it. To make it especially interesting, see if both of you can comeup with an interesting or clever way to word the headline.
160. If you could run away from it all and start fresh somewhere new, wouldyou?
His answer will speak volumes about how happy he is with hiscurrent life. If he jumps at the question, with a faraway look in his eyes, heis probably not very satisfied with his current life. If he has a hard timedeciding, it probably means he is pretty happy where he is.
161. If you were given $20,000 to throw an amazing party, gathering, orevent, what would that look like?
Depending on what kinds of get-togethers he likes, thisquestion can have some wildly different answers. Will it be a crazy party orlow key and classy? Perhaps just close friends or maybe the wholeneighborhood?
162. When was the last time you felt completely out of the loop?
This can be an interesting question, or a bit dull. It alldepends on his experiences. Perhaps it’s a crazy trend his friends were doing,and he just wasn’t into it. Maybe it’s just something that happened at schoolor work.
163. What are some small pleasures that make you way happier than theyshould?
Yeah, this one can go in all sorts of directions. But that’swhat makes it fun. And whatever direction it goes, at least you’ll know alittle bit more about him!
164. What’s something you boycott but don’t make a big deal of boycotting?
Ah, the low-key boycott. Maybe it’s on ethical grounds ormaybe it’s just a grudge. Whatever it is, I’m sure there is a story behind it.And who knows, maybe you’ll end up boycotting whatever it is after you hear hisreasons.
165. What social media post has really stuck with you?
There are probably quite a few, so he doesn’t have to pickjust one. And as a heads-up, this question definitely has the possibility ofgetting a bit heavy. Sure, it might be something positive, but it could equallybe something traumatic.
166. What common piece of advice or words of wisdom don’t actually makemuch sense?
A lot of things can sound profound, but when you look closerat them, they fall apart. Like “To understand someone, you need to walk a milein their shoes.” Sure, the meaning behind it is solid, but the actual phraseseems to encourage shoe theft and is generally unhygienic.
167. If you had to be stuck at one age forever, what age would you choose?
If he is a bit on the younger side, this question might notwork as well. I mean, you can hardly make an informed decision about being anage if you’ve never been that old.
168. What’s an example of a modern masterpiece?
It doesn’t have to be high art, it can also be TV shows, movies,books, games, or really almost anything. It’s a good question for finding outsome of the things he’s really into.
169. What useless bits of information have you memorized and will probablynever forget?
We all have trivial bits of mental detritus that just stickaround even though we have no use for them. It can be interesting to hear whatweird things that other people have got stuck in their heads as well. Ifnothing else, it’s good for a laugh.
170. What quote has always stuck with you?
It’s not a quote that he has to live by, just one that hepicked up and enjoyed. It could be a creed that he tries to follow, but itdoesn’t have to be.
171. What’s the weirdest thing you’ve seen while driving?
This question is premised on him driving, so if he doesn’thave a car or you live in a place where you usually use public transportation,you might want to give this one a pass. But if he does often drive, this canactually lead to some pretty cool stories.
172. What would be the worst animal to be eaten by?
Morbid? Yes. But it is highly unlikely he has ever beenasked this question or even pondered its answer. So, make sure you give him abit of time to process it and come up with a creative answer.
173. On a scale of existential crisis to living the dream, how’s lifegoing?
A fun, lighthearted way to ask how well he is doing, andpossibly a way to get an honest, heartfelt answer in return. Because if he ishaving a hard time, this can be a good intro to let him get some things off hischest.
174. Besides religion and politics, what topic always gets heated in yourcircle of friends and acquaintances?
Really this could be anything, sports, a game, or somethingtotally different. But what it will tell you is what he and his friends talkabout regularly and what they are passionate about.
175. If you could show everyone in the world one image for 10 seconds, butit couldn’t contain text, what image would you choose?
Another question that takes some creativity to answer. Itcan be a fun one, especially if he gives it some thought. Will he go forsomething to help people? A joke? Something for personal gain? Give thisquestion a shot and find out.
176. What looks like it should taste better than it does?
Feel free to limit it to only food, or if you wanted to openit up a bit, you could ask what non-food items look like they would taste good.
177. If there were an Olympics for average people, what would some of theevents be?
This question can be really fun once you start listingthings and going into the details of how the event would be carried out andwhat the rules would be.
178. What would the exact opposite of you be like?
You can learn a lot about someone by asking them thisquestion. Because even though they might be reluctant to tell you a lot aboutwho they are, often, people are more likely to share what the opposite ofthemselves would be. It’s also great for you to think about to learn more aboutyourself.
179. Would you travel to a foreign country all by yourself?
If this question seems a little too tame, you could alwaysspice it up a bit by asking what countries he would not travel to alone.
180. If States could date, who would be into who and why?
This one is mostly for readers in the United States, so ifyou don’t live in the United States, you might want to give it a pass. AlthoughI suppose you could substitute cities for States if you think that would workfor your country.
181. What’s something commonly done, but if you explained it to someoneoutside of your culture would sound completely insane or at least a really badidea?
Sometimes it’s easy to forget that what we consider normalin our culture might seem bizarre to other cultures. So, it can be helpful totry and hold a mirror up to our culture to keep it in perspective. Plus, it canbe pretty funny/thought-provoking to view your culture from the outside lookingin.
182. What would you recommend to someone if they had the day off and didn’tknow what to do?
Sure, if you ask him what he would do on his day off, hewould have an answer. But I think this is a more interesting way to ask thequestion. Maybe he thinks days off are best used to relax and recover, or maybethey are more for getting things done, or perhaps they are for improving one’sself.
183. What do you imagine the lives of super-rich people are like?
Not necessarily the CEOs and investors, more the people whocome from ultra-wealthy families. The ones that grew up rich and knew nothingelse. Perhaps their lives are just like average people but with nicer stuff,but somehow, I doubt it.
184. What’s the biggest “scene” you’ve seen someone make in public?
Who doesn’t love a big dramatic spectacle out in public?There is a reason you get everyone looking at the person/people, and thatreason is that humans just can’t resist a show. Be prepared for a great story!
185. What fictional character did you / do you have the hots for?
Maybe it’s someone from a book, an animated series, a comicbook, or something else. Steer clear of real actresses or actors because thisone is all about the fictional character, not the actor /actress.
186. What’s your bestpodcastrecommendation?
So, whether you ask this question depends a lot on whetheryou both listen to podcasts. If neither of you does, you should. But if both ofyou don’t, just skip this question. If he does, but you don’t, maybe give it ashot.
187. What happens more often than you’d like?
Life can’t always be a bed of roses. And if it was, whowould want to lay in it? Ask him this question to find out some things that geton his nerves. Everyone likes to get some complaints off their chest every nowand then.
188. What genetic modification would you most like to have?
Nothing is off the table! He wants a monkey tail? Boom,monkey tail. Wings? Boom, wings. But they’ll have to be big if he wants to fly.It’s fun to think about the different possibilities and usually pretty funny ifyou think about how those modifications would play out in day to day life.
189. What was something you loved, but it never really took off or wasended before it’s time?
It’s probably going to be a TV series, but it could also bea book series or maybe even a game. Whatever it is, he probably has some fondmemories he’d like to share with you about it.
190. Who would you want to play you in a movie about your life?
A great question to ask if he is into movies. Less so if hedoesn’t know many actors. If you do go for it, make sure to let him know theactor doesn’t have to look like him.
191. What would be the absolute best pet to have?
Let’s assume for this question that any animals can bedomesticated. There are all kinds of fun pets he could choose. And make sure toask why and what the pet’s name would be.
192. What’s a piece of advice that you wish everyone would take to heart?
Another question that tries to get at how he views the worldand what he thinks is important. This one gets at what he thinks some of theflaws of people are and how they should be fixed.
193. What’s one thing you learned this week?
It doesn’t have to be something big; anything will do. Hemay not be able to think of anything offhand. If that’s the case, feel free tolengthen it out to a month or a year.
194. What’s the dumbest rule you’ve been forced to follow?
It’s impossible for people making rules to foresee everypossible problem with them. So, there are bound to be some rules that justdon’t work at all once they are put into practice. Quite a few rules aredownright counterproductive. Now you can hear about the ones that bug him themost.
195. What’s the most absurd thing that has become part of reality?
There is a reason some people think we might be living insome kind of Matrix-like simulation. It’s crazy out there y’all. What are someof the things he finds particularly absurd that have come to pass?
196. Do you think your childhood was better or worse than other people growingup in a similar place and time?
Here is another question that can be a bit of a landmine. Ifhis childhood was a happy one or even just a normal one, this question willprobably stay on the casual side. But if his childhood was a particularly badone, it can get pretty heavy. Nothing wrong with heavy conversations, you justhave to choose the right time and place for them.
197. What’s your most common first thought when you wake up?
There are so many different answers that people come up withfor this question. It can really be pretty entertaining to hear about people’sfirst thoughts in the morning.
198. If you had a disease named after you, what would be the symptoms?
Another creative, kind of wacky one. Have fun with it, anddon’t take it too seriously. You could also talk about treatments or cures.
199. What’s one minor regret you have?
They don’t all have to be soul-crushing regrets. Maybe heregrets going with the salad instead of the soup at that one restaurant. Thisquestion is about those regrets that don’t really matter, but still, you wishyou hadn’t chosen the path you did.
200. What’s the single most important thing you have done in your life?
For the last question, I had to make it a big one. Find out what he thinks is his most shining glorious achievement.
If you are looking for another big list of conversation questions, try our 500 good questions to ask.
Questions to ask a guy PDF and Image
Here’s an easily printable PDF version of the first 50 questions to ask a guy.
Or there is an image 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 area lot more questions to ask a guy to choose from!
