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A great question to as a guy. This one is probably my favorite in this list of questions to ask a guy. People will be laughing and ridiculing lots of things that are popular now. And since everyone loves talking about what annoys them, well, this is a great question to get a conversation going. A question that is great on a lot of levels. There really are a lot of directions you can take this question. You can easily move the conversation to a lighter rant about generally annoying things.

And it can also tell you a lot about what he thinks success is.

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To keep the conversation going, keep switching out the celebrity. One of the best questions you can ask a guy. Just remember to talk about the small things that would change as well. It requires some thought to answer but can lead to some great conversations.

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Great ammo for some good natured teasing later on. This one can really lead to a serious conversation but sharing doubts can be an chat with guys way of creating a strong bond between two people. He gets to show off some of the things he knows, and you get to learn some new stuff.

You can discuss how societal norms might change, or how it would affect the progress of technology. A great introspective question that everyone, including you, should ask themselves. He probably has a couple. A fun question that can lead to some really creative answers. But it can be a great question to find out how important friendship is to him. We all have things or people that we absolutely hate. I know not everyone is into history. Whether those doubts are about the world at large or ourselves.

And who knows you might even get to try something new and amazing! 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 chat with guys. This is always great because usually he can show you. Who knows, you both might share an interest in the same thing or you might have never heard about it. Find out what embarrassing things he was into when he was a. Lots of double standards to choose from.

This seems like a simple and straight forward question, but it actually tells you a lot about what traits he values in other people. This one is always great for a laugh. Also a great conversation starter as there are more than few celebrities that have fallen from grace. Yeah this one is a little bit of an odd one to go out on. So make sure to use this question with caution! Because as a guy I can tell you we do some incredibly dumb and unusual things in the name of a good time.

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But I like it. We all have doubts. He was weird too when he was. So many.

Either that or he is just super clumsy or forgetful, which is also good to know. 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. And it can tell you a lot about chat with guys guy as well. Okay, so I debated whether or not to put this one into the list. You might also try moving the conversation to talking about some small annoying things about being a guy. This one may or may not have the same answer as question 34 and is probably related to question So who has he met that changed his outlook on life?

It might be a relative or a friend, or it might be a hobby, or something else entirely. You could further the conversation by trying to think of the incantation that would go with the spell. Before we start, remember chat with guys ask lots of follow up questions to find out more and to keep the conversation going.

You can see how quickly he can think on his feet and how creative he is at solving problems. 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. 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.

Perfect for finding out more about his interests and perhaps even some of his goals. We all have silly and useless talents, now you can learn about his! Kind of a random question but it can lead to some really interesting answers. This one is mostly to get him to tell a good story. We all have causes that we hold dear.

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Here is a great set of unique questions to ask a guy. What kind of hidden talents does he have?


A seemingly simple question that sometimes can lead to a really long discussion. They are deed to get an interesting conversation started, and so some of the questions are a bit off the beaten track. Which can be good or bad depending on what you are after.

This one can be good to see if the guy is a prankster, and if so, what kind of pranks he finds funny. Basically an open door to a political discussion. A great question for seeing what values he thinks are important. He might not admit it but he probably still likes peeing in the snow and building sand castles. But it definitely can chat with guys to some very interesting conversations if either of you are at all interested in politics or history.

It will also let you know what kinds of things he is into and what he considers important. Some examples might be: unclog a drain, make toast slightly more brown, unjam a copier, etc. All kids are weird in their own way.

The answers can get a bit serious and dark but I really do think this is a great question. 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. Just think about how many people will say they are an above average driver. This will give your guy a chance to tell you a good story and is a great way to get him talking. There are so many phobias out there.

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Another question that is fun to answer and gets a really unique conversation going. You can find out what types of things stress him out and you can also see how high strung or laid back he is.

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If they are though, make sure to ask them lots of details of why they like the game so much. 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.

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Here is a list of phobias in case you want to have a look. A fun question to answer, but also very informative. Well now you can find out his green eggs and ham moment. Memory is a severely flawed thing after all! We should always be questioning our beliefs and trying to find truth even if it can be a bit uncomfortable. But if you really like this question you might try our deep conversation topics or deep questions to ask a guy.

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This is a fun one to answer. It will let you know a little bit more about his past, how he views himself, and what he considers important. You can find out what morals he considers to be most important and what activities he finds detestable. So now you can find out some embarrassing and probably funny things about his childhood. Whoever or whatever it is, it or they are probably very important to him.

A little self introspection is always a good thing. Really dive into how everyday life would change if it was more like the movie he choose. But it can sometimes dig up some emotional memories so use this question with caution. Here is another creative one.

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Well now is your chance to find out more. This question is likely to get you some cute answers. Everyone likes to think they are experts at lots of things. 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.