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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 | July 26th, 2021
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If you're searching around for some deep questions to ask a guy, I have you covered!
From how to start a conversation with a guy to asking the right questions to ask a guy, I've covered it all. It's time to dig deeper with some deep questions to get to know him better.
Let's deep dive into these thought-provoking questions!
via: Bigstockphoto/ Dean Drobot
These are the very best of the deep questions to ask a guy. You can’t go wrong with these thought-provoking and interesting queries.
And don’t shift gears after they reply - use their answer to learn even more about their background and their interests!
Here are the 17 best deep questions to ask a guy:
This personal question dives deep into people's fears. Both are a risk - which way does he lean?
This gives insight into how trusting he is, and how resilient he is.
Did it affect him positively or negatively? This interesting question will be able to give you a different perspective about his personality.
Can a relationship survive this level of betrayal?
Sliced bread? Indoor plumbing? The internet? There are countless answers!
And is he doing something to make it a priority? People's lives become more meaningful when we work on what we're passionate about. This makes for a great conversation.
via: Unsplash / Nick Duell
Ten bucks bets he learned it from his Grandma.
Whether it's a sense of humor or bravery, there is something that he values most.
How much of a growth mindset does he live in? This makes of an interesting conversation starter. We'll all learn something from this.
Maybe an artist, a revolutionary, or a place? Whatever it is, it tells you a lot about him.
What does he think gives people the push to step out and go after them? Most people might have the same answers to this. Hopefully, it's not their biggest regret yet.
via: Unsplash / Josh Hild
It could be certain foods or smells, or maybe it's a holiday tradition.
Was it on purpose or an accident? Did he make it right? You can either go into a deep conversation with this one.
What unfinished business needs to be wrapped up? It's the intimate questions like this that are not small talk material. If you want a meaningful conversation, go for this.
The difference is how action-based a person is. One thing isn't above the other, though.
Which one is the more significant motivator? Which one produces the most results?
Did everything flash before his eyes? This conversation topic can get a little serious, so tread lightly.
via: Bigstockphoto / fxquadro
If you want some questions to ask a guy to get to know him, this sub-list will help you learn more about how he experiences the world.
Here are 16 questions to ask to get to know him:
If his answer is anything like, "throw a tantrum," it's a hard pass. This one is a good question to identify the best kind of men.
What's at the top of his bucket list? This one can also make it in a 21 questions game.
What are the most admirable things? What are the worst possible things? What is people's favorite thing about them?
Dive deeper. What does free will mean anyway? Let's hope no awkward silence ensues because this is one of those hard questions that is also a fun question to talk about.
It's going to inevitably happen - what can be done to deal with that fear? But be careful with this! Some people's biggest pet peeve is this topic.
Find out if he is an adrenaline junkie. Get the craziest thing they did out in the open.
via: Unsplash / Andrew Neel
No more hunger, peace abounding, the ability to teleport... there are endless answers!
Just a reminder, the first one is if you don't have anything nice to say, don't say anything at all.
An innovator will have a different opinion than an advisor.
How does he know someone is his best friend?
Free for all, first come - first pick, designated jobs? What does his ideal system look like?
via: Unsplash / averie woodard
The beach or the mountains? Maybe a different time?
Is it punishment, or fear?
Does he wish he had a different process?
Mine would be, "you can do hard things."
The supernatural or the ultra-complicated, anything goes.
via: Bigstockphoto / AntonioGuillem
This is an excellent collection of questions to ask a guy you like to learn even more about him and show him that you're interested!
And don't be afraid to send some clear visual clues you're into him, too. Make the most of this one-on-one time!
Here are 16 questions to ask someone you like:
Is there a checklist or just a feeling?
Not just the definition of character, but what does he do? Dance around with his cat? Drink milk from the carton? Read classic novels?
Does he know any couples who have met through an app?
Get the romantic questions in. This love question will give you a good idea of how he is in a romantic relationship. Which core value is the most important? You don't have to be a relationship expert to have input.
He'll know from a past relationship. Many people have a specific trigger for true love, like wanting them to meet your family or never screening their calls. This can be one of those flirty questions that you use to flirt with him when he answers.
Not joyful, not content or ecstatic, just happy. It can be meeting a celebrity crush, going to their favorite place, or watching their favorite movie.
via: Unsplash / Sebastián León Prado
An around-the-world adventure isn't the worst thing, or maybe visiting with all of his favorite people. This is the right question to find out what he wants to do.
Someone breaking our trust can be our biggest turn-off. But can trust be rebuilt? What are the steps for that, and who gets to decide?
Is it a real memory, or just a story he's heard retold over and over?
Is a simple "thank you" enough, or does he like to be more elaborate?
Relationship questions should include this one. Some people are touchers, and some are not. It's best to know which in advance!
via: Unsplash / Elizabeth Tsung
This one is a cute question. He probably will laugh retelling it. Come up with a funny question like this to make him smile.
Ask him what a successful life means. It differs from one person to the other.
Does it depend on who the stranger is? Or are they willing to sacrifice their life for any other person?
"I was right" are some good ones. A witty answer will make this more enjoyable.
What about the idea of soul mates?
via: Unsplash / Christin Hume
Are you looking for some fun questions to ask a guy? This list is a great one to break out when you're on a fun, adventurous date or when you want to amp up the silliness!
Laughter grows trust which grows intimacy - build on that!
Here are 17 deep but fun questions to ask:
Or does it depend on our season of life?
It probably is something like a sentence that starts with, "you always..."
Something from a slasher movie? Or maybe a scene from the Hangover?
What does that mean in relationships?
Also, can he fix things?
This is an excellent way to see how self-aware he is.
via: Bigstockphoto / Dean Drobot
Flying cars and healthy cake for every meal??
What does privacy genuinely mean, and is it important?
What brought him to that place?
Hint - ask this on a first date just to get the ball rolling!
Are we in the matrix?
via: Unsplash / Josh Riemer
Is faith a part of his life?
How much power does he feel he holds over his future?
What if they were made that way through trauma?
What would you do first? How would you go about it?
What needs to be checked off the list for success?
Does he feel that he or someone else has the highest expectation of himself?
via: Pexels / cottonbro
Questions that dive deep don't have to be serious all the way. These funny questions to ask a guy eke out some of his inner workings while still keeping things light!
Use this list in your uber or while waiting for your table at a restaurant!
Here are 15 deep but funny questions to ask:
Is it different than eating fish from the store?
It takes 10,000 hours to become an expert. But, what if a passion takes over your life?
And what makes us different from other wild monkeys??
What about fear or time?
And who gets to decide? It's in the eye of the beholder, after all.
My guess is it’s too hot to smile...
via: Unsplash / Joshua Hanson
Do you think electronic step counters are accurate?
What are some creative ways to reuse?
And would you leave a map?
Most of us have a moment like this burned into our minds.
And should we call them jokes?
via: Unsplash / Giorgio Trovato
Is it a dying industry?
Mine would start with a montage.
Can you train your mind to let go?
Bathroom jokes, gallows humor, or something else?
via: Bigstockphoto / Rido81
Get into some philosophy! These interesting questions to ask a guy will get his gears spinning and help you discern just how to sync your views on things!
But never fear if you have ultra-different perspectives - you may have a lot to teach each other!
Here are 17 deep, interesting questions to ask:
How can we prepare??
What is AI, and how does it impact humanity?
I mean, everyone wanted to be a veterinarian!
Are they a threat to relationships, or do they offer a shift in perspective?
It's ok sometimes to have a judgy face.
If not, what do you think lies after this life?
via: Unsplash / frank mckenna
Find out now how carefully you need to tread.
And, has he committed any crimes?
Is it just a weak spot or a character flaw?
And if so, how does he start those conversations? How do people react?
If so, what made the shift?
How big of changes? The city he lives in? His career? Becoming a vegetarian??
via: Unsplash / Brooke Lark
Does he learn best in the discomfort or when he has the freedom to learn without risk?
What was the outcome? Was it worth whatever risk he took?
What is he afraid people might see?
Or are there some things that will always threaten us?
Maybe cracking knuckles or loud conversations in public spaces.
via: Unsplash / Stefano Intintoli
Use these random questions to ask a guy to play your version of speed dating. Set a timer and go through this list, alternating answers.
Here are 19 deep random questions to ask:
Should people be of the same religion, or can families have mixed backgrounds?
What is his ideal balance of alone time to connection time?
Failure? Losing himself? Something else?
What are some big triggers? Are they the weirdest thing ever?
And work isn’t just a job! A passion project counts, too.
via: Unsplash / Marten Bjork
Right can mean so many things. How can we know we are going in the right direction?
Love can be an anchor for good or evil.
Have him give you three reasons why! And then maybe you can debate about it.
This is a practical one - a spendaholic can be a dangerous partner.
Is it zeros in a bank account, a job title, acclaim? Something else?
If not, what's the long-term plan? We all have different views when it comes to this topic.
Ask about his methods for checking against his own wisdom.
How does his family support them?
via: Unsplash / Patrick Schöpflin
What does he look like whole-hearted?
Can we live a meaningful life without it?
For good or for bad - get a realistic answer
Make sure to think through other people's anniversaries and his own.
Who decides the value of a life?
How long 'til he was found out? If it took long enough, ask him for some tips! The guy's got some talent.
via: Unsplash / Harli Marten
Make sure you use these personal questions to ask a guy with care! Like all of these questions, you may tread on tender ground. Have fun, but hold space for him to be vulnerable.
Here are 15 deep personal questions to ask:
Or is it intermixed?
Nature versus nurture is an argument for the ages.
Hidden talent? Hidden fear? Or is everything just hidden deep down?
And is it different depending on who is telling the story?
Fear? Love? A desire to better the world, starting with this person?
Ghosts, gravity or otherwise? They say you have to see to believe, but is that always the case?
via: Unsplash / Stefano Pollio
Let’s go over the storyline of Inception once more.
How long was it before you were able to put it aside as in the past?
Does the salary load need to be equally distributed?
Is it weird long skirts and big vans or prodigy-style kids graduating early?
The goals version of "is it better to have loved and lost."
What about trade school? Is there a more socially acceptable path?
The heart, the mind, or outside the body?
via: Unsplash / Sharon McCutcheon
Does he feel like the earlier generation is outdated or that they have timeless wisdom to share?
Let’s say, top 4?
via: Pexels / Vanessa Garcia
When you're ready to take your relationship to another level, try using these deep questions to ask your boyfriend to make a stronger connection.
Here are 3 deep questions to ask your boyfriend:
Big questions like this are always a great way to spark deep conversations.
This is nice to ask to see how he defines accomplishment.
Our struggles don't define us so much as they shape us to build deeper character-a great question for anyone, not just people who have lived a hard life.
Here is a downloadable and printable List of Deep Questions To Ask A Guy (right-click the image and select Save Image As...):
via: Galtelligence
via: Pexels / Anthony Shkraba
If you're not sure how to go about these deep questions and conversations, we've got the answers for you.
You can always start with questions that aren't too personal. Start with simple questions that are light and funny, and work your way up from there.
Never ask him about topics that are sensitive for him. You can always ask in advance what issues he doesn't want to talk about.
It depends on how well you already know him. If you're not too close yet, it will be more challenging to get him to open up to you.
If you have an open mind, there's less chance of it affecting your relationship. However, there are times when your values might clash. It's best to talk about it to ensure that nothing gets hurt.
Keep an open mind and be respectful. You can always ask if you expand so that you can understand his side better.
via: Unsplash / Priscilla Du Preez
Wondering how to sort through this in-depth list of questions? I've made a quick guide to help you choose questions that add depth and affection to your relationship, not add stress.
Here is how to pick the best questions to ask:
via: Unsplash / Akson
Gauge how you and your crush are doing emotionally. Are you having fun? Are you feeling connected? Is there underlying stress?
Get a good read on how much bandwidth you have when choosing questions and having deep conversations.
via: Unsplash / Alexis Brown
Read through this list, and choose questions that fit where you are-feeling playful? Go for some light-hearted questions. In a thoughtful mood? Try asking some of the more meaningful questions.
These questions can also be great for easing some tension - choose some of the funnier questions, and let the silliness relieve the stress.
via: Bigstockphoto / Alessandro Biascioli
While many of these questions could be answered quickly, let them be a diving board into some deeper conversation!
Remember, this isn't a checklist! Maybe just one of these questions leads to days of conversations for you and your guy. Let the conversation take its winding course, pressure-free.
If you want to learn more ways to talk to guys, we've got you covered.
I'm sure these deep questions to ask a guy will lead to many fun, familiar conversations! Family, work, fears, hopes, and existential dread - this list covers all the bases, and there hundreds of curious questions to ask a guy to start building a deeper connection.
As you plan out how to start a conversation with a guy you're interested in, try busting out some of these fun discussion topics! These are bold and surprising ways to get the ball rolling or take a relationship to new levels. Have fun!
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