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Getting a guy to talk about himself can be a challenging task. But with the right set questions, you will be surprised! Start picking and asking some of those questions, get a conversation started, and form a connection. You won’t regret it.

Remember to always ask some follow up questions if he is interested in the topic.

List of questions to ask a guy

Here are our 200+ quality questions to ask a guy:

1. What was your best drop the mic moment?

Who doesn’t like telling an extraordinary 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.

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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 sandcastles. 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.

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3. What’s the most considerable 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.

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5. 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 chooses. 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.

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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 talk 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.

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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.

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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 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.

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 from finding out he was a 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, 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.

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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 treehouse, 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 badass treehouse getaway 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 exciting 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 leaders 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. It’s great ammo for some good-natured teasing later on.

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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, as they say, “Great men are seldom good men”.

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.

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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 the 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?

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30. What double standard is ridiculous and needs to be ended?

There are 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 profound 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 exciting conversations if either of you is at all interested in politics or history.

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 dedication 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.

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34. If you died today, what would your most outstanding 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?

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 huge impression on you?

As 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 to get to know more about him.

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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 fascinating 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 you’re familiar with green eggs and ham. Well, now you can find out his green eggs and ham moment. We’ve all been in a situation where something we thought was stupid turned out to be amazing. And who knows you might even get to try something new and unusual!

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 books or doesn’t have a favorite author, that’s also great to know!

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45. When you are daydreaming, 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 the 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 so much if they aren’t. If they are, though, make sure to ask them lots of details of why they like the game so much.

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52. What’s the best prank you can play on someone?

This one can be good to see if the guy is a prankster, and if 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 bit and then give you an answer. And even if he isn’t into history, he’ll probably be 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 just trying to be friends with him, so feel free to pass it by if you are trying to keep things more casual. But it can be a great question to find out how important friendship is to him.

55. What would be the worst thing to have a phobia of?

There are so many phobias out there.

56. Who or what do 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 probably very 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 answers can 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 him the chance to vent?

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59. What’s the best bad decision you’ve made?

I’m sure he’s made a few bad decisions that he wouldn’t take back. Time to find out what those bad decisions were because there is usually a 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 and has 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 build of 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 their childhood? Everybody likes to reminisce sometimes, and the chances are that he will too.

63. What are some things people have selflessly done to make your life better?

This question is great for getting at how grateful he is for what others have done in his life. And if he doesn’t think that anyone has selflessly done anything for him, he has either had a rough life, or doesn’t appreciate the 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 creative with it. Humans have a ton of euphemisms for all sorts of things. Now it’s time to 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 else entirely. Whatever it is, he probably has a few stories about the item or the people who comment on it.

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66. If you could level up in life just like in video games, where would you put 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 of geekiness.

67. What have you done wrong for most of your life and only recently found out the right way to do it?

This question can be good for a laugh. The funniest stories are when they learned how to do something the wrong way in childhood and didn’t learn the right way until WAY late in life.

68. How does your definition of a “real man” differ from the mainstream stereotype of a “real man”?

This question can be quite revealing because it gets at the specific values that he thinks are worthwhile. It will tell you a lot about how he views the world and his place in it.

69. What’s your perfect burger?

The most exceptional American question ever. And quite entertaining! It will let you know a little more about what tastes he likes and doesn’t like.

70. Which fictional villain is your favorite?

You could also follow this up with a favorite hero, but it’s usually more interesting to hear about which villain he likes. It could be because he thinks the villain had a point, or he might just think the villain looks cool.

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71. You’re given up to $300,000 to make one room in your house or apartment ridiculously amazing, what room do you pick and what upgrades do you make?

A great question for pulling out some creativity and finding out what his ideal space would look like. Also great for finding out what kinds of 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 real life? Maybe he has seen one in real life - or did it himself. I’m sure it would make 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 of games. 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 question is a good round-about way to find out his views on masculinity and gender in general.

76. What’s the weirdest thing you used to eat as a child?

Kids eat weird stuff. I did. You probably did too. And he probably did too. Time to have a laugh at some of your childhood weirdness.

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77. If time wasn’t an issue and you had forever to master a skill, what skill would you master?

A great question for finding out more about his interests and 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 are both from the same place or different places. It’ll let you or know what it was like growing up where he did or if you are from the same place, you can have fun brainstorming together and maybe getting some good ideas for things to check out.

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

Another one that is great for stretching creativity. And feel free to think of more than one thing to make it a bit longer of a discussion. This question can lead to some very unexpected conversations.

80. What are you so incredibly terrible at, that you’ve given up ever doing it again?

It can be endearing to hear and talk about failures, and this question is great at pulling out failures without being too negative about it.

81. What was the last movie that made you cry?

This question might give you a rough estimate of how sensitive 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 things that maybe we don’t need to worry about, but we still do.

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83. If you could add 4 hours to your day, what would you spend that 4 hours doing?

Chances are, whatever he mentions is something he wishes he could be accomplishing now but just can’t find the time or energy for.

84. What’s something everyone should experience at least once in their life?

A good question to get into a conversation about meaningful experiences 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 own country or some other country.

86. What’s your earliest memory?

Memories are weird slippery things. Most of our memories are flawed, especially the early ones, and some are outright false. But that doesn’t mean they can’t be used for a good conversation!

87. What do you think is the most confusing idiom for people learning English?

So, this is kind of a weird one. If you don’t think it will fly, feel free to skip it. An idiom is a saying that takes on a different meaning than the literal meaning. For example, he dodged a bullet or she’s between a rock and a hard place.

88. What are some websites you used to use all the time but have stopped using?

Ah, our personal website graveyards. The ones we used to visit almost every day but haven’t thought about in years. Perhaps it’s Myspace, Livejournal, or Newgrounds. But whatever the site, he certainly has one or three. And it’s always fun to reminisce.

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89. Who would be the worst celebrity to have dinner with?

This is a play on the old conversation starter “Who in history 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 pointed it out?

You know, the things that make you feel stupid and say, “Oh yeah, that makes sense.” It’s always great to share embarrassing stories and have 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 and how 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 ask follow-up questions to find out why they chose that item and feel free to ask what 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 is probably no exception. And who knows you might just find your new favorite flavor combination!

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

We can all be hypocrites at times, but the real trick is being able to notice that we are doing. That takes some self-awareness, and it’s always good to know if the person you are talking to has that self-awareness.

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95. Where have you traveled?

Who doesn’t love a good travel story?! And who knows you may have visited some of the same places, but even if you haven’t, it can be good to chat about the places you’ve both been to.

96. What obscure website do you absolutely love?

This one is a bit hit or miss, because they may not visit many obscure websites. But if they do have a favorite one, well, now you’ve got an 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 about something that they’ve seen or experienced first-hand because that always leads to better stories. But if they can’t think of anything off the top of their head, there are always feel-good news stories about acts of kindness. You might even be able to transition the conversation into nice things they’ve done for others.

98. What’s the most useful skill you’ve ever learned?

I like this one because you never know what they’ll come up with. And it actually can tell you a bit about what their world is like and what skill sets they have.

Like most hypotheticals, this one gets better, the more creative you get with your answers. The fun of it is imagining what that trend will lead to once it gets out into the world.

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100. When was the last time you remember someone doing or saying something so stupid that you were sure it was a joke?

You know the situation, someone says something or suggests something, and you laugh and laugh, thinking it’s a joke. But then they look at you all weird, and you realize they weren’t joking.

101. What was the most historic thing you witnessed in person or took part in?

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 be something he was forced to learn for his job. Either way, he’ll probably be able 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 entire Earth would be one unified political body. What would be the capital city of Earth? What would its flag and anthem be?

So, this question is definitely a bit out there. But it can be a lot of fun if he is creative and enjoys hypothetical questions. If it’s a question you think he’ll be interested in, you can both spend time brainstorming together.

104. What’s the best $5 you’ve ever spent?

Answers to this question are all over the map. You never really know what kind of answer you’ll get. But there is a good chance he has never been asked this question, so hurray for novelty!

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105. What movie really encapsulates the era it was made in?

Basically, what 80’s movie was the most 80’s? What 90’s movie was the most 90’s? This can be a bit hard if you are both young because the 2000s got kind of all merged together, but you might be able to salvage something from this question even if you are both on the younger side.

106. What fictional character is portrayed as a hero but is actually more like a villain?

It could be an action hero that goes around destroying people’s property and livelihoods, causing car crashes and general mayhem. Or perhaps a hero whose actions bring about horrible unintended consequences. Either way, it can be fun to think about the traditional hero’s journey in a different way.

107. What was a random compliment someone gave you that really stuck in your memory?

Compliments, people should give more of them. They don’t cost anything, and they make someone feel awesome.

108. If you could go back in time and inspire someone to make a present-day invention, what invention in what period would advance humanity the most?

Okay, I know, this is almost like an essay question. But if he 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 being creative, you might want to give this on a pass.

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109. What’s your phone and/or computer wallpaper?

This seems like a weird question, but it can be surprisingly telling. And most likely, he has reasons why he chose the wallpapers. Whatever it is, even if it’s just the stock wallpaper, it will tell you a little bit about him.

110. What’s your favorite board or card game? How about your least favorite?

With his favorite, he’ll be more than happy to tell you about it. With the least favorite, there is a good chance that there is some story behind it. Maybe it’s a family member that always beat him, or it’s just generally rage-inducing.

111. What was the worst thing you ever tasted?

This is another question that you never really know what kind of answer he’ll come up with. But whatever it is, there is probably a good story 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, or perhaps throwing stuff around? Maybe he’ll get more playful with his haunting, or perhaps he’ll go with the horrifying approach. This one can be a really great one if you are both into horror movies/shows. And it’s easy to transition into a discussion about horror in general or ghost stories.

113. What’s one small thing a person can do each day that greatly improves their life?

This question is good on its own but is also good for transitioning into a conversation about habits in general. Or you could transition it into a conversation about self-improvement.

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114. What makes you special and unique?

This question is a little more personal. It seeks to understand what they think makes up the core of who they are or at least what sets them apart from others. It might also lead to a dead-end because a lot of people haven’t thought about what makes them unique, so he might not have an answer 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’s conscious, but more often it’s unconscious. He may or may not answer this one truthfully, because to answer it truthfully, well, you have to confront your own prejudices.

116. What movie quote are you tired of hearing?

There are so many movie quotes that get repeated again and again, and again. Years after the movie came out. So which ones is he fed up with?

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 interesting answer 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. Whatever those two things are, he can probably talk hours about them. And if he can’t think of things he’s passionate about, well, you can always transition the question into “What are some of your favorite things to do?”.

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119. What must be seen or experienced in person to really appreciate it?

This is another question that you never know what direction he’ll take it in. But whatever direction he goes, it’s sure to be something that 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 or spice that they just loathe and can’t eat whatever it goes into. For me, it’s those big bean sprouts. But everyone is different, and it’s a good question to ask 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, Keanu Reeves, or Jennifer Lawrence. Some celebrities are bound to be jerks. If you can’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 because they might think you are insinuating that they aren’t “manly”. But if they are good at fixing things, they probably will enjoy talking about it. You’ll just have to read how you think he’ll take it.

123. What’s the first thing that you think when seeing a homeless person?

Talk about a loaded question. This will tell you a lot about how he views others and how compassionate he is. And if you both don’t have the same view, it can definitely lead to an argument. So, handle this one with care.

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124. What’s the most ridiculous tattoo you’ve ever seen?

Oh boy howdy are there a bunch of terrible tattoos. After you’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 be good 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 could 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 a fun question. Because everyone loves a good ghost story, even if in the end you find out that there were no ghosts. You probably have a few unexplained stories as 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 movies in 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. Just remember to reverse the order of the main plot points that happen and not the specific details.

To help out with this question, think about what was legal and normal 20 years ago but is now illegal. You’ll get the general gist and be able to think about some examples that will be illegal soon or relatively soon.

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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 he comes up with. It’s also interesting to see how much time he’ll put into thinking 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 probably plenty of things that even though he has had a lot of practice, it’s still just not 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 at heart seem to have the most fun. This question is good for getting to know him a little better and growing closer by sharing things that he probably doesn’t tell 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 but wouldn’t do again. A lot of times, there is a pretty good story behind it as well.

133. If you could pick up any musical instrument and instantly be a virtuoso 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 him time 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 are usually pretty cheesy, they can still be fun. And who knows you might even find a one-liner you can use later.

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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 on his 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 are annoyed by them anyway?

Sure, they aren’t really serious, but they can still be annoying. Chances are if he grew up in a prosperous country, he probably has experienced some first world problems. I’m sure you have a few too, so why not commiserate?

137. What do you collect?

You never know what he might like collecting. People collect all kinds of things. I think collecting things might be something fundamental to 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 behind it. Usually, this one is fine, but if he was in a car wreck or something similar 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 you would never return to Earth?

Some people love testing boundaries, exploring, and going to the edge of human experience. And some don’t. No judgment either way, but it’s good to find out where on the spectrum he is. Maybe he’d join the second or third wave? Or maybe he’s quite happy here on Earth.

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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 if they aren’t for a store you like. Find out what shops he loathes with this question.

141. When was the last time a stranger made your day?

Who doesn’t love a feel-good story? And strangers helping strangers is a wonderful example of human goodness. Or it might be something funny 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 do yet?

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 to curing the common cold, but he might come out with something a lot more interesting.

143. What’s your creative outlet?

This is a fantastic question to get to know him better. Make sure he knows that “creative outlet” can be nearly anything. It doesn’t have to be something traditional, like painting or playing an instrument. It can be playing a game, fixing up a car, cooking, social media, or something completely different.

144. When was the last time that things got a little too real?

You never know what he’ll come up with this one. Things getting a little too “real” is pretty subjective, so it kind of depends on how he interprets the question. It can be a fun one for discussion, though, or at least for a good story.

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145. What do people idealize, but really shouldn’t?

It could be a trend, a celebrity, a value, or something totally different. This one can lead to an in-depth discussion of society. If you aren’t into that or don’t think he would be, you could always give this one a 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, it should be easy to come up with a few examples.

147. If you could add one rule that everyone must follow when they use the internet, what would your rule be?

A fun hypothetical question that can lead to some entertaining or serious answers. Because let’s face it, the internet is not always the best place. It could definitely use some improvement.

148. What’s worse than you thought it would be?

Another question that could have any number of different answers depending on his experience. It could be something funny, something serious, something personal, or something that happened to society.

149. What have you really wanted to do for a long time but haven’t done yet?

Sure, it might be a major goal that they’ve been thinking about tackling for a long time. But it could also be something small and insignificant that they just haven’t gotten around to.

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150. What’s the worst slip of the tongue you have heard about or that has happened to you?

Slips of the tongue can be disastrous, hilarious, and/or deeply embarrassing. But whether you cringe or laugh, it’s sure to be something entertaining that you’ll enjoy.

151. What activity or hobby is so filled with hateful people that it puts you off trying it?

This is kind of a hit or miss question. It all depends on whether they know about a hobby or activity with a hateful community. But if they have played any online multiplayer games, they’ve probably run into at least 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 be surprised 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, or YouTube?

If you have heard of the person, you can have a chat about some 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 hilarious material 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’s also a way to point out some of the joys of daily life that we don’t always appreciate. You might even find out after thinking about this question that there are parts of your day you love but haven’t really thought about much.

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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.

156. What language do you like the sound of, even though you don’t know how to speak it?

This is another good one because so many people have different opinions about what languages sound the best. And then you can transition 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 about movies that each of you likes. You can also talk about which genres you both like as well. You might even get some awesome movie suggestions for genres you aren’t normally into.

158. What’s your definition of a good human being?

This one can be as deep or as shallow as he wants to make it. And everyone will have a slightly different take on it. After all, the topic is one that philosophers have been asking for as long as there have been philosophers.

159. What news headline would you most like to see?

This can be an interesting one. Especially if he puts some thought into it. To make it especially interesting, see if both of you can come up with an interesting or clever way to word the headline.

160. If you could run away from it all and start fresh somewhere new, would you?

His answer will speak volumes about how happy he is with his current life. If he jumps at the question, with a faraway look in his eyes, he is probably not very satisfied with his current life. If he has a hard time deciding, it probably means he is pretty happy where he is.

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161. If you were given $20,000 to throw an amazing party, gathering, or event, what would that look like?

Depending on what kinds of get-togethers he likes, this question can have some wildly different answers. Will it be a crazy party or low key and classy? Perhaps just close friends or maybe the whole neighborhood?

162. When was the last time you felt completely out of the loop?

This can be an interesting question, or a bit dull. It all depends 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 school or work.

163. What are some small pleasures that make you way happier than they should?

Yeah, this one can go in all sorts of directions. But that’s what makes it fun. And whatever direction it goes, at least you’ll know a little 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 or maybe 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 his reasons.

165. What social media post has really stuck with you?

There are probably quite a few, so he doesn’t have to pick just one. And as a heads-up, this question definitely has the possibility of getting a bit heavy. Sure, it might be something positive, but it could equally be something traumatic.

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166. What common piece of advice or words of wisdom don’t actually make much sense?

A lot of things can sound profound, but when you look closer at them, they fall apart. Like “To understand someone, you need to walk a mile in their shoes.” Sure, the meaning behind it is solid, but the actual phrase seems 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 not work as well. I mean, you can hardly make an informed decision about being an age 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 out some of the things he’s really into.

169. What useless bits of information have you memorized and will probably never forget?

We all have trivial bits of mental detritus that just stick around even though we have no use for them. It can be interesting to hear what weird things that other people have got stuck in their heads as well. If nothing 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 he picked up and enjoyed. It could be a creed that he tries to follow, but it doesn’t have to be.

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171. What’s the weirdest thing you’ve seen while driving?

This question is premised on him driving, so if he doesn’t have 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 can actually 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 been asked this question or even pondered its answer. So, make sure you give him a bit 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 life going?

A fun, lighthearted way to ask how well he is doing, and possibly a way to get an honest, heartfelt answer in return. Because if he is having a hard time, this can be a good intro to let him get some things off his chest.

174. Besides religion and politics, what topic always gets heated in your circle of friends and acquaintances?

Really this could be anything, sports, a game, or something totally different. But what it will tell you is what he and his friends talk about regularly and what they are passionate about.

175. If you could show everyone in the world one image for 10 seconds, but it couldn’t contain text, what image would you choose?

Another question that takes some creativity to answer. It can be a fun one, especially if he gives it some thought. Will he go for something to help people? A joke? Something for personal gain? Give this question a shot and find out.

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176. What looks like it should taste better than it does?

Feel free to limit it to only food, or if you wanted to open it up a bit, you could ask what non-food items look like they would taste good.

177. If there were an Olympics for ordinary people, what would some of the events be?

This question can be really fun once you start listing things and going into the details of how the event would be carried out and what the rules would be.

178. What would the exact opposite of you be like?

You can learn a lot about someone by asking them this question. Because even though they might be reluctant to tell you a lot about who they are, often, people are more likely to share what the opposite of themselves would be. It’s also great for you to think about learning more about yourself.

179. Would you travel to a foreign country all by yourself?

If this question seems a little too tame, you could always spice it up a bit by asking what countries he would not travel alone.

180. If States could date, who would be into who and why?

This one is mostly for readers in the United States, so if you don’t live in the United States, you might want to give it a pass. Although I suppose you could substitute cities for States if you think that would work for your country.

181. What’s something commonly done, but if you explained it to someone outside of your culture would sound completely insane or at least a really bad idea?

Sometimes it’s easy to forget that what we consider normal in our culture might seem bizarre to other cultures. So, it can be helpful to try and hold a mirror up to our culture to keep it in perspective. Plus, it can be pretty funny/thought-provoking to view your culture from the outside looking in.

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182. What would you recommend to someone if they had the day off and didn’t know what to do?

Sure, if you ask him what he would do on his day off, he would have an answer. But I think this is a more interesting way to ask the question. Maybe he thinks days off are best used to relax and recover, or maybe they are more for getting things done, or perhaps they are for improving one’s self.

183. What do you imagine the lives of super-rich people are like?

Not necessarily the CEOs and investors, more the people who come from ultra-wealthy families. The ones that grew up rich and knew nothing else. Perhaps their lives are just like ordinary 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 that reason 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 comic book, or something else. Steer clear of real actresses or actors because this one is all about the fictional character, not the actor /actress.

186. What’s your best podcast recommendation?

So, whether you ask this question depends a lot on whether you both listen to podcasts. If neither of you does, you should. But if both of you don’t, just skip this question. If he does, but you don’t, maybe give it a shot.

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187. What happens more often than you’d like?

Life can’t always be a bed of roses. And if it was, who would want to lay in it? Ask him this question to find out some things that get on his nerves. Everyone likes to get some complaints off their chest every now and 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 if you think about how those modifications would play out in the day to day life.

189. What was something you loved, but it never really took off or was ended before it’s time?

It’s probably going to be a TV series, but it could also be a book series or maybe even a game. Whatever it is, he probably has some fond memories 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 he doesn’t know many actors. If you do go for it, make sure to let him know the actor 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 be domesticated. There are all kinds of fun pets he could choose. And make sure to ask 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 world and what he thinks is important. This one gets at what he thinks some of the flaws of people are and how they should be fixed.

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193. What’s one thing you learned this week?

It doesn’t have to be something big; anything will do. He may not be able to think of anything offhand. If that’s the case, feel free to lengthen 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 to make rules to foresee every possible problem with them. So, there are bound to be some rules that just don’t work at all once they are put into practice. Quite a few rules are downright counterproductive. Now you can hear about the ones that bug him the most.

195. What’s the most absurd thing that has become part of reality?

There is a reason some people think we might be living in some kind of Matrix-like simulation. It’s crazy out there y’all. What are some of the things he finds particularly absurd that have come to pass?

196. Do you think your childhood was better or worse than other people growing up in a similar place and time?

Here is another question that can be a bit of a landmine. If his childhood was a happy one or even just a normal one, this question will probably stay on the casual side. But if his childhood was a particularly bad one, it can get pretty heavy. Nothing wrong with heavy conversations, you just have to choose the right time and place for them.

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197. What’s your most common first thought when you wake up?

There are so many different answers that people come up with for this question. It can really be pretty entertaining to hear about people’s first 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, and don’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 he regrets going with the salad instead of the soup at that one restaurant. This question is about those regrets that don’t really matter, but still, you wish you 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.

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Conversation Starters

Looking for some conversation starters and icebreakers? Check out our collection of articles full of tips, tricks, and ideas to help get the conversation flowing! Get to know how to talk to anyone anytime, anywhere!