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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by Jasper | March 23rd, 2022
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Why is it important to know the right random questions to ask a guy?
Because there's nothing as dreadful as a boring conversation. Everyone has something interesting to say if you ask the right questions, and there is no limit when it comes to questions to ask a guy; they can funny, personal, flirty or deep depending on your relationship.
Whether you're wondering how to start a conversation with a guy or how to connect with a guy you like, you can never go wrong with our list of random questions. They are spontaneous and playful, and therefore spark interesting and unexpected conversations.
via: Pexels / Elena Buzmakova(borisova)
You only have once chance to make a good first impression. Some random questions will lead to a great story, some will have a surprising answer, and others may even bring up embarrassing moments from the past. Either way, these best random questions will keep the conversation alive.
Here are the 13 best random questions to ask a guy:
How vivid is his imagination?
Let his inner boy scout come out to play and marvel at his excellent (or lack of) survival skills.
We all feel like we're in a dream sometimes, and it's okay.
Changing something's name also changes the way people think of it.
Snails, snakes, and crocodiles don't count.
Everyone has boundaries, keep that in mind when thinking of what are some random questions to ask to get to know someone.
There are some shockingly hilarious cell phone covers out there.
via: Pexels / Bich Tran
That one person you can't take anywhere because something bad always happens when they're around.
Ever find yourself rooting for the bad guy? You're not alone.
Maybe he has a good book you can borrow.
We can't be good at everything, and there's nothing wrong with that.
This one's a thinker.
You can never go wrong with this one.
via: Bigstockphoto / Zinkevych
Getting to know a guy (or anyone for that matter) is all about having the right conversations with them. When considering random questions to ask a guy to get to know him, you want to go for questions that are genuinely curious and not too pushy or accusatory. We've got you covered.
Here are 13 random questions to ask a guy to get to know him:
Self-awareness is important, find out if he has mastered this rare skill.
What's his idea of unwinding after a long day at work?
We all have those moments in our past that we like to revisit now and again.
Between love, trust, and commitment, which matters most to him?
Appearances may or may not matter to him, but fashion expresses who we are and sometimes how we feel inside.
A good question to find out what values matter most to him when it comes to raising children.
via: Pexels / Vidal Balielo Jr.
A lot is wrong with the world we live in. If given a clean slate, how would he fix it?
This will give you insight into his personality, and it's a plus if you plan to take things to the next level.
Find out about his heroes and the people he looks up to.
This question is not as simple as it seems. Give him a chance to explain.
Difficulties in one's job can often spill over and affect their personal relationships.
Someone's taste in music defines who they are. You might even find out that he is currently part of a garage band.
What is it about that place that makes it appealing to him?
via: Bigstockphoto / DisobeyArt
Before getting serious with a guy, you should get to know him more. These random questions to ask a guy you like are guaranteed to get him talking.
If you like him, you have to know.
Phone call anxiety is a real thing, but maybe he can make an exception for you.
Is he a last-minute kind of person or does he like to plan ahead?
The nature of a guy's relationship with his mother can reveal a lot about his personality and how he treats women.
via: Pexels / Suzy Hazelwood
Sometimes, you owe it to yourself to be clear about your boundaries and the consequences of crossing them. Does he feel the same way?
Humor is a coping mechanism that we all need, but find out where he draws the line so you don't cross any boundaries.
A good question to uncover his deepest desires.
Tears are not a sign of weakness. Find out if the guy you like is in touch with his emotions.
And can he have one without the other?
And what does it take to keep a relationship with him going?
via: Bigstockphoto / Dmytro Sidelnikov
Conversations don't always have to be serious. When thinking of what are random questions to ask, make sure to consider fun questions to ask a guy that can lighten the mood and make him open up. Sometimes, it's okay to keep it casual.
Did the place make him feel lost or free?
Maybe he prefers having fun alone or in a group; fun wears many faces, so keep an open mind when asking this one.
A better way to ask if he is a morning person.
Or does he put on a full hour-long show?
via: Pexels / Sachith Hettigodage
It's not as simple as flipping a switch, but if you know, you know.
Rejection is inevitable, how well can he handle it?
When thinking of what are some random questions to ask, include those that talk about fear, too.
The world needs more people that focus on opportunities, not problems.
via: Pexels / Immortal shots
A shared sense of humor can strengthen relationships. With these funny questions to ask a guy, you can laugh and be silly together.
Here are 8 random funny questions to ask a guy:
Maybe you even share some of the same embarrassing fears.
Siblings have been known to fight each other over food, so...
Ask him to sing it for you.
Sexiness is in the eye of the beholder.
via: Pexels / Jan Krnc
Was it an accident or did he do it on purpose? And would he do it again?
He might have to wear the lipstick first, or at least eat it.
That is if he can even survive the week.
Animals always seem to ignore people when they talk; it would be fun to get inside their brains.
via: Bigstockphoto / Dean Drobot
The secret to having great conversations is asking the right questions. Interesting questions to ask a guy can reveal the most unexpected things about him.
Here are 9 random interesting questions to ask a guy:
This question always reveals the guy who knows what he wants from a relationship.
Is he all about healthy living or quick and easy meals?
Don't let him trick you. ost people say they are feminists even though they don't understand the meaning of the word.
What about reincarnation?
Its the worst but still, better to have loved and lost.
via: Pexels / Jan Krnc
Hopefully, he's not too polite for his own good.
The brain is a muscle and it needs exercising to stay sharp.
Remember, it's not all black and white- you can have both stability and spontaneity.
For most guys, its the smile.
via: Unsplash / Etienne Boulanger
Deep questions tend to be too serious at times. But if you really want to get to know someone on a personal level, then you have to ask the deepest questions. Our list of random deep questions to ask a guy can help you create stronger bonds.
Here are 13 random but deep questions to ask a guy:
And what's the story behind this rule?
As we grow up, it can be heartbreaking to find out that our parents are just as normal and confused about life as we are, but we still look up to them.
As we grow up, it can be heartbreaking to find out that our parents are just as normal and confused about life as we are, but we still look up to them.
They say we should age gracefully, but can he really give up youth that easily?
The dilemma of love is that the more you have, the more you have to lose.
Should men and women be treated as equals both in the workplace and in their households?
This one roughly translates to: do you think we have free will?
via: Unsplash / James Wheeler
Did the fairy tales lie, or is Prince Charming somewhere on the other side of the world waiting for us?
Forget all the movies you've watched where vigilantes save the day. In real life, things are just a bit more complicated.
Depression is nothing to be ashamed of, but it can take a toll if not treated.
We may have evolved into more intelligent beings, but could modern human beings survive in an uncivilized world?
There are so many things children need to learn, but he only has to pick one.
Schools tend to teach technical things and not nearly enough life skills to help students survive in the real world.
In a future where machines do all the work, what will humans do?
via: Pexels / fauxels
Having random questions to ask someone handy can help you whether you're getting to know a guy, or you are simply looking to have an interesting conversation. However, not all guys are the same, so pick your questions carefully.
Here is how to pick the best random questions to ask a guy:
via: Pexels / Lê Minh
The nature of your relationships determines the type of questions you can ask a guy. Some questions are more personal than others, so it all depends on who the guy is. A personal question may not be appropriate when getting to know a coworker, but it may work on a first date. So, when thinking of what are random questions to ask, consider the stage you are in. Always.
via: Pexels / Trinity Kubassek
If you happen to ask a question that a guy is not comfortable answering, don't push it. Take the loss and move on before it becomes awkward.
via: Pexels / mentatdgt
A conversation is not all about asking and answering random questions. These questions to ask a guy as only here to act as a guide. Listen to the guy you're talking to and allow the conversation to flow naturally.
Here is a downloadable and printable List of Random Questions To Ask A Guy (right click the image and select Save Image As...):
via: Galtelligence
When you like a guy, it's normal to be a little nervous around him. If this happens, don't worry. We have more awesome tips and questions that can help you get through your next hundred conversations.
Here are more great ways to talk to guys:
There you have it; a dependable list of random questions to ask a guy. Once you figure out how to start a conversation with a guy, all you have to do is pick the right questions to ask a guy.
These questions will help your conversations along and get your crush, your guy friend, or even your boyfriend to open up some more.
You may get unexpected answers, but its all part of the process. And we'll be here to help you on how to tell if a guy likes you or if he's worth your time and effort.
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