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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
via: Unsplash / Helena Lopes
Having all sorts of fun questions to ask a guy gives you everything a gal could need to break the ice, show interest in a guy you like, get closer with someone special, and much more.
Curiosity can be an incredibly attractive trait, so knowing what questions to ask a guy can immediately make you that much more interesting.
In a lot of ways, being a good conversation partner starts by being willing to listen, so asking questions is a powerful way to get the ball rolling with just about anyone.
Ready to get started? Take a look at our hand-selected list of fun questions to ask a guy, and you'll never run out of options for making every conversation more fun and interesting.
via: Bigstockphoto / Alessandro Biascioli
What are some fun questions to ask? They are your go-to questions, the cream of the crop for when you really want to make a fun impression on a guy. Try them out anytime you're feeling curious about a guy, and you'll see just how powerful they can be for making connections.
Here are the 11 best fun questions to ask a guy:
Tap into his flair for adventure with this question, and you just might find yourself going on one together soon.
Buyer's remorse is a common thing for just about everyone.
Is he more easy-going and composed, or a bit on the impatient side? Either way, everyone has something that they're willing to wait for.
Almost everybody has a "third place" – where you go between work and home. Whether it's a bar, coffee shop, or the gym can say a lot about what sort of guy he is (and if you might be compatible).
via: Unsplash / Toa Heftiba
At its core, this question asks about whether he is humble enough to ask for help.
Or, said another way, does he believe that "ignorance is bliss"?
Our passions make life interesting – both our own, as well as the lives of those around us. Asking him to share his passions with you can be an amazing way to connect on shared interests.
This question asks whether he is more of a leader or a follower. Which do you prefer?
If not, what could he do to change that?
A bucket list is a great indicator of someone's biggest dreams, and this question will show you his life goals, making it one of the best fun questions to ask someone.
Does he see himself more as a tough-guy type, or the shy and sensitive sort?
via: Bigstockphoto / Dean Drobot
When something about him really catches your attention, that's the perfect time to pull out these questions to ask a guy to get to know him. A little bit more intimate, these questions inquire more deeply and specifically so you can see how compatible the two of you are as friends... or something more.
Here are the 8 best fun questions to ask a guy to get to know him:
You can find out whether there's common ground for your happiness with this question, because everyone should have something in their day that makes them happy, whether it's a perfect cup of coffee or being woken up by a beloved pet.
What we identify with can shape the whole course of our lives. Do his defining characteristics make him more or less attractive to you?
Flirty and playful, this question is a quick way to see just how into you he might be... without coming across too strongly.
Of course things change as we grow older, but that doesn't mean we let go of the fond memories of our first dreams as a kid; this one taps into those special memories.
via: Unsplash / Jordan Whitt
If he's willing to reveal even a small secret to you about himself, that's a definite sign of interest.
Most guys have had to endure some sort of physical hardship in their life, sometimes by choice and sometimes not. Ask this question to connect on what sort of challenges he's overcome in his life.
Humor connects people, so knowing the answer to this question can give you even more ways to get to know each other.
This one is an absolute throwback! And a great way to bring up pleasant feelings of nostalgia.
via: Bigstockphoto / monkeybusinessimages
So, you're definitely interested in him – now you need some questions to ask a guy you like. Keep it fun, flirty, and just a little bit on the more personal side to make sure he knows you're interested in him.
Here are the 7 best fun questions to ask a guy you like:
Save this one for when you can tell that he's interested in you, too: It can lead to deep, meaningful conversations about what both of you really want out of a relationship.
If you really like him, it's important to start thinking about whether the two of you might have a future together – and that requires strong skills for keeping a relationship strong and healthy.
Being a good cook can be very attractive; does he want to show off for you?
via: Unsplash / Edgar Castrejon
The people we look up to help guide and shape our lives, so knowing who his biggest influence is can tell you a lot about the deeper parts of his character.
When you ask this one, if he replies with something that's related to you, it's an obvious sign of interest... and an invitation to continue getting to know each other even more.
Questions like this help you to know whether you're on the same page. Do you both want committed relationships, or is this more of a casual dating sort of vibe?
Let's face it: jealousy can happen to all of us. It's important to know whether the two of you match up on how strongly you feel about jealousy.
via: Bigstockphoto / Rido81
Sometimes the mood is just right to stay away from the serious stuff and embrace your comedic side with some fun but also funny questions to ask a guy.
Here are the best 9 fun but also funny questions to ask a guy:
Asking about his mischievous, childish side can open the door to all sorts of fun and funny conversations.
I mean, I'm pretty sure everyone has... So this one is more asking whether he'll admit to it!
Smell and memory are intimately linked, so even just asking this question is a surefire way to spark some interesting memories.
Twilight is such a love-it-or-hate-it movie that just about everyone has strong opinions on it – which can lead to fun and funny joking about the whole thing.
via: Unsplash / Priscilla Du Preez
Random and quirky, sure – but it also gives you an idea of whether you might end up cooking for each other someday.
Bonus points if you ask to see pictures of it!
If he's willing to share this, be sure and give him a little bit of teasing for just how gross it is!
Mustard, mayo, and ketchup might have to battle it out to see what his favorite is.
via: Bigstockphoto / JacobLund
One of the best ways to make sure that guys will want to keep talking to you is to come off as fun and interesting with the questions you ask. You can use our curated list of interesting questions to ask a guy to make sure that you'll never be accused of being boring.
Here are the 8 best fun interesting questions to ask a guy:
Travel is one of life's most fun and interesting pursuits and can provide insight into what he likes doing most.
It's a question that gives him an opportunity to boast a little, and also show off his good side.
This gives you two a chance to cringe together at who is more of a klutz.
Ask this one if you want a great excuse to go out for a drink together.
And if so, did you believe what they told you?
via: Unsplash / Kristina Flour
This conversation can be deep, and really tell you a lot about whether he is willing to take responsibility for his life.
Choosing a character will always show more of how he sees himself, even in non-obvious ways.
There are 5 of them – do you know yours?
via: Unsplash / Yanapi Senaud
Sometimes you just need to throw caution to the wind and go for the most random questions to ask a guy. Whatever happens next, it's guaranteed to be interesting!
Here are the 7 best fun random questions to ask a guy:
No wrong answers on this one!
Everyone has a pet peeve, so you can be sure that he'll have a good answer for this one.
Because underwater basket weaving is a thing, you know.
A great follow-up is to ask them "when was the last time you wore it?"
via: Unsplash / Ruthson Zimmerman
Is he an expert gardener, or barely able to keep a houseplant alive?
… And incognito windows count, too!
Because everybody has one of those stories!
via: Bigstockphoto / photosvit
When you're really feeling that spark of connection, that's the perfect time to look for deep questions to ask a guy. The more time you spend together asking these sort of questions, the deeper your vulnerability and connection to each other can grow.
Here are the 9 best fun but deep questions to ask a guy:
Everybody makes mistakes, so this question always gives the two of you common ground to have a conversation about.
The gender divide can be a huge deal, and this question gets right to the heart of how he feels about women in general.
Their answer will tell you a lot about what's most important to them.
Human potential is amazing – some say limitless. What does he think is the biggest priority for people everywhere?
This powerful, direct question lets you know whether his life is an open book, or whether he is the secretive type.
via: Unsplash / Debby Hudson
Personal goals are a sign of responsibility and commitment to self-improvement, two very desirable characteristics in a guy.
The way a guy treats servers and bartenders says a lot about how he treats people of all economic backgrounds.
A great follow-up question: Which sense would you absolutely not give up, and why?
Tough times really show peoples' deeper character.
via: Pexels / Andrea Piacquadio
It’s always a good idea to keep it light and enjoyable when texting. That’s why these fun questions to ask a guy over text are always a solid plan.
Here are 5 fun questions to ask a guy over text:
Guys usually love video games, and they’ll probably find it really amusing and fun to answer this question. Bonus points if you both love gaming, because then you can bond over your shared interest.
via: Unsplash / Alex Haney
While this question is fun, it can also be quite revealing. What you’re really asking here is “are you a good teammate?” It’s a pretty important thing to know if you’re thinking about a relationship.
A lot of guys will probably lie if you ask them this question - but there’s always a few that will be honest and tell you all about their hilarious adventures on dating apps.
Everyone loves to talk about their travels, and he’ll probably have all kinds of interesting stories to tell you about his world travels.
There are probably a few good reasons to break the law on rare occasions… But it’s fun to see what his reasons would be.
via: Pexels / Israelzin Oliveira
Remember, you can keep it flirty and fun at the same time. A great way to do that is to consider these fun yet flirty questions to ask a guy.
While some of these questions might have no right or wrong answer, the “right” answer in this case is pretty obvious - of course he should be making breakfast in bed for that special girl!
via: Unsplash / Toa Heftiba
So many amazing fictional worlds to choose from… Will he be transported to Middle Earth, or into the Star Wars universe? Maybe you’ll both end up in the same world…
This is a fun question when you’re texting, because it kind of sets things up for an in-person date - especially if he claims to be better at flirting face-to-face.
via: Pexels / Talal Hakim
When you choose personal questions to ask a guy that are fun at the same time, you can keep things light while still learning a lot about him.
Here are 3 fun but personal questions to ask a guy:
Almost every guy had at least one crush on a teacher… and learning about it is pretty funny. That being said, it also tells you what they find attractive in women.
Sometimes, guys answer these questions in a funny way. Other times, they get pretty serious - even dark. You never really know what you’re going to get with this question, and that’s why it’s so good.
This is such a fun question to ask over text. Start out with some light and fun questions, and then ask him some deep questions to see what kinds of images he sends.
via: Pexels / Dmitry Zvolskiy
via: Pexels / Charlotte May
Still a little confused as to how to pick the best fun questions to ask a guy? Try these four simple steps.
Here is how to pick the best fun questions to ask a guy:
via: Unsplash / NeONBRAND
Try it like this: Pick at least one question from each category, practice them a few times out loud, and you'll be more likely to come up with the right question naturally.
via: Unsplash / Kate Kalvach
When thinking about what are some fun questions to ask, it always helps to keep in mind where you're at. Loud, funny questions aren't any good for a library... But a loud club at 2 a.m. isn't the best place for deep questions, either!
via: Unsplash / Kyle Broad
Sincerity goes such a long way in getting to know somebody – so listen to your intuition, and choose the questions that are most genuinely interesting to you.
via: Unsplash / Hannah Olinger
When you're thinking about how to phrase the question, try to include the person's name, and maybe reference to how you think it applies to something you already know about them.
Here is a downloadable and printable List of Fun Questions To Ask A Guy (right click the image and select Save Image As...):
via: Galtelligence.com
Looking for even more great ways to talk to guys? This list is an awesome place to start, but it's always a good idea to be prepared for anything.
We've got you covered:
You have so many great, authentic, and fun questions to ask a guy now – so go with your gut, and you'll figure out the perfect one for each situation!
No matter which of these options you choose, having plenty of questions to ask a guy will always leave you well-prepared for whatever comes up in conversation. Be yourself, do what comes naturally, and you'll definitely find the success that you're looking for. Never find yourself looking up at the clouds again when thinking what are some fun questions to ask!
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