What Are Some Funny Questions to Ask a Guy?

Home $ LIFESTYLE $ RELATIONSHIPS $ What Are Some Funny Questions to Ask a Guy?



When it comes to having a conversation with someone that you do not know very well, it can be incredibly difficult to come up with a good starting question. After all, the right thing to say will depend entirely on the situation at hand, how well you know the person you are talking to, and what your relationship is with this person.

Some questions are better to ask girls rather than guys, and vice versa. If you want to talk to a guy and you do not know where to start, you might find yourself sputtering for the right words to say, and nobody wants that to happen.

To make the most out of your conversations, you should try and think about what kind of conversation starters you could use. One of the most universally preferred conversation starters are questions that you can ask someone. If you are just wanting to get to know this person, you might want to brush up on some funny questions to ask a guy.

No matter if you are just trying to get to know a coworker a little bit better or you want to get closer with a guy that you know, then you will want to think about some questions that you could ask to start a conversation with.

However, you might not know what kind of topics this man is interested in. If you ask a stereotypical question about sports or hunting, you might not come across in a way that the guy could find appealing. Instead, you should consider asking a question that has less to do about the fact that the person you are talking to is a guy, and more with the fact that you want to get to know this person. First things first, the questions you ask should be based on the situation at hand, as some situations call for different kinds of questions.

Judging the Situation at Hand

To make the most out of your conversation with this guy, you will want to first get a good grasp of the situation you are talking to him in. If it is a casual, public setting, then more personal questions may not be the best thing to ask him. On the other hand, if it is a one-on-one conversation, you may want to take this opportunity to get to know the guy a little bit better.

If it is a situation where you know next to nothing about the person you are talking to, then you may want to ask some starting questions about the guy, what he does, and what he is interested in. Likewise, if you are talking to someone that you have known for a while, but you simply don’t know what to talk about, you can consider a fun conversation starter to get the talking going. Asking the right questions at the right times can make all the difference in how well you end up getting along with this guy.

Casual Questions to Ask a Guy

If you are in a casual setting where you and a guy are just talking about anything that comes to mind, without much of an ulterior motive behind the questions, you may want to think about some simple and calm topics to ask about.

Depending on how well you know the guy, some of these questions could also help you get to know the guy better. These questions will be a focus of both getting to know the guy you are talking to and simply starting a fun conversation that anyone could join in. With these types of questions, you will want to avoid getting too personal with them or prying too deep into sensitive subject matters. These questions are best for fun, simple conversations.

You could consider asking a question like “What movie can you watch repeatedly and never tire of?” as a good starting question. Here, you can learn more about the taste in movies the guy has, what his particular interests are, and you can start a fun conversation about favorite movies and movie scenes. Similarly, you could ask what the most interesting piece of trivia he knows is.

If the person you are talking to is interested in trivia, this can often lead to a long discussion of strange facts that you might not even know. You could also ask a question such as “What is the worst purchase you have ever made?” as these questions can often get into interesting stories about strange purchases.

Questions to Get to Know a Guy

If you are just getting to know a guy, you may not want to dive headfirst into personal questions and questions that would open the guy up too much for a first-time discussion. Instead, you should stick to simple questions that will give you a good idea of what the guy enjoys, what his personality is like, and so on.

More often than not, these questions tend to stay in the realm of “What is your favorite?” or “What would you do in a certain situation?”, but no matter how creative these questions get, they can tell a lot about the person you are talking to.

Of course, you can always start with a simple “What do you think you are the worst at?” to begin discussions. However, if you want to get into more creative questions that don’t come across like a questionnaire, then you could consider asking a question such as “What’s your definition of a good person?” to really start off a good discussion and see what his values in a person are at the same time. If you want to keep things casual, you could circle back to “What would your ideal burger look like?” or something similar to that.

Questions to Get to Know a Guy Even Better             

If you are ready to begin really getting to know a guy, but you do not want to directly ask him to spill his biggest secret, there are plenty of questions that you could ask that would give you a good idea of who the guy you are talking to is like, deep down inside. These questions are better reserved for guys that you personally know, as they can sometimes lead to sensitive discussions about personal moments in their lives. These are often not the best questions to spring onto a guy you don’t know too well, but are better for a deep and lengthy discussion about values.

A typical place to start could be “What is the worst thing you have ever done?” or “What do you regret the most?” as this can usually lead to long conversations about the hardest moments in the guy’s life, as long as he is willing to open up to you. If you want to dive into controversial or sensitive topics, you could ask the guy’s opinion on whether or not all people are equal, and what he might think about that. Similar questions can involve “What would you expect from a partner?” or “What makes you insecure?”.

Questions to Start a Conversation

Finally, there may come a time when you are hanging out with your friends and the conversation seems to die down and nobody really knows what to say. This happens naturally with the ebb and flow of conversation and it also becomes the perfect time to ask a conversation-sparking question. These questions are often long, open-ended, and leave a lot of room for interpretation.

You could consider asking “If you ran into a celebrity, what would you say?” and you could specify which celebrity it would be, depending on the group interests. You can ask common questions, such as “What superpower would you have if you could choose anything?” as this can often start a long conversation about superheroes, superpowers, and just about anything supernatural. You could ask questions about where people would travel, or what they would do if money wasn’t a limitation. The possibilities are, quite literally, endless.


Recent Posts