Conversations can be awkward sometimes, awkward to start, and uncomfortable to maintain, especially if you are talking to a guy you like or have a crush on. But, on the other hand, having a fun and lively conversation with a guy can require some effort, whether on a proper date or a simple hangout, and you do not want to come off as dull or drab.
The best way to break the ice in these kinds of situations is to develop a list of engaging questions. Here’s a secret, guys love to talk about themselves (Don’t tell anyone I told you so). So there are good questions to ask a guy that guarantees you a lovely time, and they can be funny, random, or even flirty if you’re feeling a little daring.
These questions help you get to know the person better and understand basic, essential, and random things about them. These questions can also be beneficial with someone you’ve known or been dating for a while.
Keep in mind when asking these questions that it is to discover and know them better, not impress or assess them. So here is a list of 20 simple, fun, and engaging questions to ask a guy you like:
1. What was your best drop-the-mic moment?
As mentioned earlier, there’s nothing the average guy loves more than telling a story about himself. His response can range from a formal event where he gave a brilliant speech or said something amusing that had everyone rolling on the floor.
Whatever the answer is, you are bound to find out a lovely story about a moment he’s proud of. This is also a great way of discovering what he considers necessary, funny, or worthy of praise. This question can also lead to other interesting and engaging questions.
2. What childish thing do you still enjoy?
This is one of the best questions to ask a guy you like because everyone has one or two childhood memories or habits that they still hold on to. It could be something like bursting bubble wraps, snowball battles, or pulling weird, funny faces.
No matter his response, you are bound to get very cute and maybe even amusing answers. To make it more interesting, it doesn’t have to be one thing. Instead, you can ask for a list of these habits and when last he indulged in them. This train of conversation will have you laughing and sharing childhood stories all through the entire date.
3. What’s the biggest doubt you have?
This is undoubtedly one of the deep questions to ask a guy you are just getting to know. In truth, we all have doubts. Allowing the guy to share his misgivings while you listen, ask follow-up questions, and share yours is a great way to form a deep connection.
It can lead to some grave and profound discovery about him and maybe even yourself. When looking for a way to move from random surface discussions into the more important stuff, this is a great way to introduce depth to the conversation.
4. What movie do you wish life was more like?
This is a rather peculiar question that can start a fascinating conversation. You would be surprised at the most random reasons he would give for picking a particular movie.
One thing to remind him of in this kind of conversation is how much of an effect his choice of the film would have on his everyday life. Remind him of the minor changes that could happen, from the kind of parents he’d have to the sort of places he would be or the type of career he’d have.
5. What is the most useless thing you know how to do?
This is one random question to ask a guy. Everyone has one or two hidden talents that are ridiculously silly or useless. This could lead to an entertaining and funny conversation.
If it’s something not too out of pocket, you can even ask him to show you. You would be learning some of the most exciting things about him, while giving him room to feel at ease and enjoy your presence. You would also be allowing for a charming atmosphere, one that could lead to even cuter things to do or talk about.
6. What’s the worst and best thing about being male?
What are some of the perceptions or misperceptions about the male gender? Here is an opportunity to find out the peculiarities of being a guy.
From this conversation, you will likely learn about the dynamism between the male and female gender, our differences and similarities, and the essential things that bind us. This question can lead to an informative and interesting conversation, especially if you ask about the most annoying things about being a guy.
7. What would you not do for 1 million dollars?
This is a funny question to ask a guy. The surest way to know it will be fun is for you to take a few moments now and think what you would do for 1 million dollars? I’m sure you can come up with some silly ideas, maybe even dangerous answers.
Now imagine hearing responses to the same questions from a guy. When asking this question, you can even come up with some fun options that you juxtapose, like a “would you rather” situation, it makes for an amusing conversation.
8. What movie can you watch over and over and never get tired of?
This is an excellent question. It can lead to him telling you about his favorite film of all time and why he loves them so much.On the flip side, you could also talk about
You can also include TV shows he prefers. This kind of information can come in handy when planning a special night or birthday dinner experience for him, so you should listen with rapt attention.
9. Which historical figure wasn’t as amazing as most people think they were?
This question is particularly engaging because we all must have heard about one historical figure or the other that wasn’t all that great. There are recurrent conversations around this topic on social media every other day, it would be impossible not to have come in contact with any of them, even if only briefly.
If he turns out to be somewhat of a history enthusiast, all you have to do is listen to him go on and on about this, there is nothing historians love more than clearing up myths.
10. What is the highest-pressure situation you have experienced, and how did you handle it?
This question can lead to a conversation similar to that of the mic-drop because it would require him to tell you stories about particular and peculiar experiences.
From this conversation, you are bound to pick up a few profound knowledge on how much pressure affects him, the things/people that can pressure him, but most importantly, how he deals with the stress. You might also learn a few things for yourself on how to deal with pressure or vice versa.
11. What are you tired of hearing about?
With the news and social media becoming more and more critical to our everyday lives, some information and stories won’t just go away, or conversations that have become tiring to hear or participate in.
This question can help you know what topics to avoid in future discussions. It can also tell you the kinds of things he considers unimportant or irrelevant. If he mentions some things you care about, this can lead to an open conversation about personal values, preferences, and perspectives.
12. What double standard is ridiculous and needs to be ended?
This is a profound question to ask a guy because society is full of hypocritical and double-standard conversations. There are too many to pick from.
This is a way of finding out just how social-media-savvy he is and if he is interested or participates in social issues. It is also a way of finding out some of his biases and blind spots, whatever you do in this conversation, do not make it into a debate. You are getting to know him, not interview him for a job or engage him in a debate, so it’s best not to get antagonistic.
13. What type of food do you like?
Food is always an amusing conversation to have because there are thousands of options to pick from. Another thing to love about food conversation is the influence our different environments have on what we consider delicacies too disgusting to eat.
If he’s well-traveled, you are bound to get some shocking, maybe even weird responses. On the other hand, if he is conservative about food, you could tease him about being culinary unadventurous and even suggest some different things for him to try.
14. What kind of music do you like listening to?
Like the food conversation, music is a global language with so many different dialects and sounds. Environment, background, culture, and friends are all significant parts of what influences the kinds of music he likes.
You can explore every sect of influence on his music taste, you could also ask him to play you some of his all-time favorite songs. If you prefer, you ask for him to make you a playlist of his kind of music. You can even exchange playlists and develop a wager to determine who has the best taste to make it more interesting.
15. Do you like pets?
Animals make for a fascinating conversation, there are so many different choices of what people can and do keep as pets. If he’s someone with the regular choice or preference of pets like cats, dogs, goldfish, rabbits, and so on, you could ask easy questions like how long he’s and how close he is to them.
But, on the other hand, he could also be one of the peculiar people whose pets are snakes, crocodiles, or any other wild animal. Then you can ask why some of these choices, listen to him explain them to you and maybe even clear up a few misconceptions for yourself.
16. What is your dream job?
Everyone knows that adulting is not a walk in the park. The reality of the world, the struggle to work, survive, and gather wealth, can be startlingly different from all the childhood dreams we had. So this question can lead him to tell you about the things he dreams about in contrast to where he is now.
In the extraordinary case that he is doing his dream job, however, you want to ask questions about the reality of the goal as different from what he imagined it to be. You might also want to ask if he now has new dreams or is comfortable where he is forever.
17. Do you like traveling?
Travelling can be a riveting conversation because you get to ask about all the places he has been to and the people and traditions he has come across. You could also ask about his favorite thing(s) about traveling, some of his favorite places, and his fondest memories while traveling.
If he happens to be a person who hasn’t done a lot of traveling, you should ask why, you can also ask for some of the places he dreams of going to and why. This information can come in handy for you if things eventually proceed into a serious relationship.
18. What’s your favorite drink?
Not only are there so many drinks in the world, but there are also so many types of beverages. You might want to know what category of drinks he fancies the most. Is he a gin and tonic kind of person, a wine lover, or a heavy coffee drinker?
Whatever his favorite type of drink is, you could ask how often he takes them, which is his favorite drink type. For example, if he loves coffee, does he take it plain black or with milk and sugar, prefers home-ground beans, or is it just an anything-goes guy? The subject of consumables is so vast and inexhaustible if you know the right questions to ask.
19. Do you believe in Karma?
As much as most people are of the school of thought that neither good deeds nor evil deeds go unrewarded, some people still do not believe in Karma. Some people feel strongly about coincidences. This is a perfect way to find out where this guy belongs on the spectrum.
This question can also lead to the primary reason we do what we do as humans. For example, if he believes in Karma, you might want to ask a question like, “so, do you do good because you genuinely want to or because you are afraid of bad karma?”
20. Do you believe in destiny?
Karma is one thing. Destiny is another thing entirely. Asking him this question is also basically asking him about his belief system. This can be a long, profound, and engaging conversation with the tendency to make you forget the time. If he happens to be areligious, you could ask what informed that choice and how he is finding the whole experience.
One thing to avoid in this conversation is directly juxtaposing your own belief with his for comparison or trying to change his mind on his belief. Research has shown that that tactic usually results in unpleasant experiences. Just be attentive, and ask questions when necessary.
Navigating conservation, especially with a guy you like, can be tricky, but it doesn’t have to be complicated. Now that we have given you 20 good questions to ask a guy, you mustn’t go on a date, questions in one hand like you are about to conduct an interrogation. Instead, let the conversation flow. Be calm, relaxed, and sweet.
You don’t even have to ask all the questions, they are coined so that one question can lead to so many other questions and exciting conversations. This is all about getting to know the guy, but most importantly, it is also about enjoying yourself and letting him feel at ease in your presence. We wish you the very best!