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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 11th, 2022
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Deep questions to ask are compelling. And they're all in this post.
Whether it's a dinner date or you want to get to know someone, we have all the best questions to ask. Personal questions and powerful questions are all the expertise we have.
Be prepared for a meaningful conversation through the heart, soul, and mind one hard question at a time. Let's go into deeper territories.
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Okay, now that you have a good idea of approaching these questions, let's go over a few deep conversation topics.
These aren't questions. They're general ideas to keep on the back burner. Our questions are perfect when you're stuck. These conversation topics can be molded to fit your exact situation. After all, there's no predicting where an interesting conversation may go.
Take these topics, and use them to form your own unique and more profound questions catered directly to your company.
Here are some of the best deep conversation topics:
Family
Childhood
Goals and Aspirations
Passions
Romance
Dreams/Nightmares
Values
Struggles
Experiences
Inspirations
The Universe
Significant Events
The Future/Past
Similarities/Differences
Fears
Society
Achievements/Failures
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These deep conversation starters act as starting points. Many of them are open-ended and can lead virtually anywhere.
Remember: conversation starters give you a topic to work with. It's up to you to keep the conversation flowing.
So, what are some deep questions that would stimulate your mind and indeed give you something to begin with?
Here are 8 of the best deep conversation starters:
What's better – a long life or a well-lived one? This conversation starters can lead to inspiring conversations. Plan an adventure now!
via: Unsplash / Sylvain Mauroux
How much value do you put on human life as a whole? What if the stranger was a child? Would it depend on the circumstances given, or would they say yes no matter the situation?
What's that lesson that has stuck with you all these years? This is an excellent opportunity for you to learn a thing or two, so pay attention to the answer.
Yesterday's dreams aren't always today's reality. What drives you now, compared to last year or even ten or twenty years ago.
This question immediately adds comforting warmness to the conversation. It can also help you to make new memories along the same lines.
They say what we think of as our biggest pet peeve, and the worst thing in the world can tell a lot about us as an individual. It's random questions like this that make you think.
via: Pexels / Keira Burton
There's always that one movie that made us want to have a better life.
Don't say you don't have a prepared answer for this profound but fun question!
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Quite simply, these are some of our best deep questions. They're the ones that really cut to the core and open up the lines of communication. They're the questions that lead to conversations that you remember long after they're over. Use them wisely.
Here are 10 of the best deep questions to ask:
This interesting question makes great conversation. This gives you a deeper connection and knowledge with who you're talking to.
This sometimes presents itself as those casual questions that we can all laugh about.
True love goes deeper than a romantic relationship. They say that memories are love's greatest preservatives. This is a great question because you get to reminisce meaningful memories. Everyone loves looking back at happy memories.
via: Pexels / Artem Beliaikin
And how close or far are they to it?
Beauty is in the eye of the beholder. It takes on different meanings for different people. This question can help you to gain a new perspective.
Whether it's lifting weights or blocking someone on Facebook, there are moments when we feel on top of the world.
Words can take on different meanings depending on the context, inflection, facial expressions, body language, and countless other factors. Is the content what matters, or how the content is portrayed?
When thinking of what are some deep questions to ask, sometimes it is better to be straight to the point. Why or why not?
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The answer to this question says a lot about how people view themselves.
It's a good conversation if the other person decides they're okay with opening it up to you!
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Whether you're dating or chilling with a platonic friend, these deep questions to ask a girl will help you connect with her in a way that lasts.
As a guy, forming an authentic relationship with a girl can be tricky. Having heartfelt questions to ask a girl shows that you genuinely care about her beyond a superficial level. It proves that you value what's inside.
Here are 10 of the best deep questions to ask a girl:
Learn about what makes her proud. Be sure to ask follow-up questions about the work she put in to get there.
This question helps you understand her best traits while also letting her brag a bit. It opens up plenty of opportunities for you to compliment her, too. Always take an opportunity like this.
It's tough to know how you come off to new people. This question can help both of you to learn about yourselves and each other.
via: Unsplash / Brooke Cagle
There's no need to ask a relationship expert for this. Sometimes, we get insightful answers from a past relationship.
Maybe you can help them achieve that perfect day.
Whether they do or don't, you'll get to know them on a deeper level.
It's better to understand it early on, so you avoid doing it to them. We all have different reasons for our bad moods, and they're all valid.
And if they don't, would they be okay with not getting a second chance?
via: Pexels / Andrea Piacquadio
We all have that one thing that just ruins everything, no matter how perfect the other person might seem.
Sometimes, challenging them to describe it in just a word makes the question a more fun conversation topic.
via: Unsplash / Anna Vander Stel
While these questions to ask a guy may not be ideal for your bar buddies (unless you've had quite a few), they're perfect for bonding with your close friends.
Your guy friends are family. In fact, sometimes they fill an essential role that your blood family can't. When you really need someone to talk to, you can count on your best friends to lend an ear.
These questions can help you to get to know a new friend a little better. They can also be used to spark a discussion with your tight friends when you just feel like making a connection with someone.
Here are 10 of the best deep questions to ask a guy:
Whether it was a good day at the gym or a hike up a mountain, physical exertion usually comes with an exciting story.
Whether it's witnessing a professional athlete or learning from a mentor, there are moments when we recognize our shortcomings, and that's totally okay.
The people you look up to say a lot about the person you are currently, as well as the type you'd like to become.
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How can we help tomorrow's men to succeed in all aspects of existence? What critical standards must be passed down?
Would he implement classes on how to prepare taxes and manage credit cards? Or maybe he would prefer more of the day was spent mastering the recorder?
It's impossible to predict what the future will hold, but it's certainly interesting to talk about.
There's always something to be proud of. Stopping a bad habit is an achievement.
If you want to have a meaningful connection with someone, it helps to know who they look up to. Chances are, they resemble that person a lot.
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It would depend on what people consider a "talent," right? Being able to sleep for the whole day might be considered a talent for some.
We all want to be remembered and be in people's lives, but how we want to be remembered says a lot about what we hold dear.
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There's always something new to learn about your partner in crime. These deep questions to ask your girlfriend help you to really understand what makes her tick.
Having deep conversations can really improve a relationship. It can strengthen existing bonds and create new ones.
Having questions to ask your girlfriend prepared keeps the relationship fun. After all, you don't want to spend your next dinner date sitting in silence.
Here are 8 of the best deep questions to ask a girlfriend:
This question can be difficult. If she doesn't want to talk about it, be an understanding boyfriend and change the topic.
Everyone makes mistakes. This is the right question to realize that. Is she willing to talk about them? It may help her to open up when you speak about your past errors first.
Learning about her family helps you to understand her better.
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This is a different way of asking who the people most important to her are. It helps you to understand the value that someone brings.
It's an essential and good question to ask if you want to treat them right and know them deeper.
It's essential to be on the same page when it comes to this. We all have boundaries, and we want those we're in a relationship to understand and respect that.
Whether the past relationship ended well or not, we all learn something from them. It's important to take that learning into the next one.
Not everyone can agree on one answer. The topic is always up for debate.
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These fascinating questions can lead to new ways of viewing the world around you. Philosophy improves your critical thinking skills. It helps you to reason better.
Spending some time dwelling on these deep philosophical questions can really help you to unlock your own mind. These deep philosophical questions can give you those light bulb moments when everything just makes sense.
When you really want the conversation to get cooking, nothing beats philosophical questions. Just make sure you respect the other person's opinion, even if you disagree.
Here are 7 of the best philosophical questions to ask:
Is there a limit to what should be allowed? Do they think being able to say anything is more beneficial or harmful?
There's a fine line between using your mind and losing your mind. At what point do you cross that line? Can you think of examples of people who went too far?
Or are they just neurons firing arbitrarily? Are our brains trying to tell us something?
You can touch matter, but you wouldn't realize it without your brain. You can imagine anything, but if you can't touch it, is it even real?
Beyond the apparent air, water, shelter, and food, what do we really require to make it in this world?
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It's a common thought that we always want to know.
This will say a lot about who they are as an individual.
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Getting to know a new friend isn't always fun and games. Sometimes, you have to bring out deep questions to ask a new friend to have more extensive knowledge of your friend.
Here are 7 deep questions to ask a new friend:
You'll learn about your new friend depending on whether they're afraid or excited about it and why.
Sometimes, the tattoos we put on our bodies mean the deepest things in the world. It can be a mirror into our soul. Occasionally, we just think it's cute.
If they say yes, be a friend and offer your time to listen to them.
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It would also be nice to know what their concept of an afterlife is! Definitely a topic worth talking about.
Maybe you can make use of that advice, too! Whatever it is, it must be terrific and mind-blowing.
If they could turn back time, would they still do that first kiss? Some would, some wouldn't. It's a good discussion to have.
We all have different views when it comes to these. Friendship and a romantic relationship are two very different dynamics, but both are very meaningful.
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These existential questions can give your brain a serious workout. Existential questions are powerful. They force us to confront our humanity and who we are at our core. They make us consider the very essence of what it is and what it means to exist.
Asking too many of these can lead to the classic existential crisis, so use them sparingly.
Here are 9 of the best existential questions to ask:
This question really makes you examine whether you're just passing the time until you die or making the most of every day.
via: Pexels / Andres Ayrton
This conversation can get heady. Sure, we're part of a society, but think about humanity as a whole. Then the possibility of other lives in other universes. Keep going bigger until it hurts.
Do we go back to where we were before we were born? Another dimension? Are we reincarnated? Do our souls go to heaven or hell? Nobody knows, but it's certainly interesting to speculate.
Do you believe in a creator? Or are we here by pure chance? Do we exist simply because we must for the universe to be truly infinite? Are we part of a simulation? What is the origin of the human species?
If you asked an ant about the Milky Way, it wouldn't have an answer. Are we simply incapable of understanding the dimensions around us?
And once we figure it out, will we be capable of achieving it? Or are we simply pawns in a game controlled by superior cosmic beings?
via: Pexels / Andrea Piacquadio
People always wonder about what happens after death, but what about before we existed? Were our souls waiting for our turn at bat? Or did they materialize as soon as we were conceived?
Is our greater purpose simply to observe the universe? We often view the universe as something outside of us, but an exciting possibility is that the universe is us.
Is time a man-made invention to keep track of our place in the universe? A relative scale? A calculation of existence? An ever-flowing river of events? A fourth dimension? The engine that prevents the universe from remaining static? An undefinable phenomenon that morphs depending on an infinite number of factors? A scheme to sell watches?
via: Pexels / Edmond Dantès
When you're ready to move from small talk to real talk, use these thought-provoking questions. These questions give your brain a workout, sparking deep discussions that enrich everyone involved.
These questions deserve attention. These aren't the type of questions you ask and then move on. Sink your teeth into them, and use them to feed other relevant, in-depth conversations.
At the same time, you must pay attention to how your conversational partner is responding. If they don't seem to be into it, move into lighter territories. Thought-provoking questions are best used sparingly, so save them for appropriate times with the right people.
Here are 8 of the best deep and thought-provoking questions to ask:
Conversely, if you have an ax and replace its head and then replace its handle, is it still the same ax?
Are we a product of our environment? Or is humanity ingrained in us?
via: Unsplash / Cristina Gottardi
On a grand scale, is positive or negative reinforcement more effective for creating change?
Can we ever reach a final destination, or are conclusions always out of reach?
This question forces you to examine what's commonly viewed as a negative trait in a positive light.
We just hope that your younger self is someone that listens to advice from an older you.
Our favorite memory, although dear to us, may feel bittersweet. However, there's a favorite memory that we wouldn't mind playing over and over again. Reliving the feeling will always feel great.
via: Unsplash / Antonino Visalli
This philosophical question will surely get both of you thinking deeper.
Here is a downloadable and printable jpg/pdf list of deep questions to ask (right-click the image and select Save Image As…):
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via: Pexels / August de Richelieu
Asking deep questions is something that we should do, but it's not always easy. We're here to help you and answer your questions.
It's okay to ask deep questions to a new friend as long as you know to tread lightly. Ask politely, and let them know you'll be asking deep questions. Give them a choice not to answer if they're not comfortable. It's always great to have some deep questions to ask a new friend so you can know them better faster!
Asking deep questions to your friends allows you to know them better. If you're able to understand them more profoundly and better, you'll have a better connection. This will help you be a better friend to them. Knowing deeper about other people also helps you look at the world from a different perspective. It's a way to widen your horizons.
As long as they don't become offended and awkward around you, you're doing fine. Always put a disclaimer before asking anything that might be too personal to ensure that you will harm no relationship.
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Starting a conversation can seem intimidating, but as long as you follow these tips, you'll be good to go.
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A first date or hangout probably isn't the best time to start a deep conversation. Keep things lighthearted until you're confident that you're comfortable enough to have an in-depth discussion with them and also that they're equally as pleased with you.
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There's a time and place for everything. If you're chatting with someone at a mutual friend's birthday, these deep questions to ask aren't ideal conversation fodder. However, if you're on a third date gazing at the stars with a bottle of wine, these conversations can really help to make that connection. Knowing where to start a conversation is just as important as knowing how to start a conversation.
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If who you're talking with doesn't feel comfortable, don't push it. Not everyone is willing to open up, and there's nothing wrong with that. Don't be offended if someone says they're not ready to talk about deep or personal topics.
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These questions carry weight. Don't fire off one after the other. Ask one, and then use the person's response to dive into the sea of conversation. Don't just ask a question, listen to the answer, and move on.
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One of the biggest mistakes you can make is keeping the conversation one-sided. If you want someone to feel comfortable opening up to you, you must open up to them too. It's a two-way street. You give, and you take. Deep questions should lead to deep discussions. This isn't an interview.
By now, you should be a bona fide deep thinker. After a few serious conversations, you might feel like the next Plato or Carl Sagan.
Of course, once you've had a taste of the power of deep discussion, the thirst for more knowledge only grows stronger. Fortunately, we have plenty of other personal questions to ask, as well as some more lighthearted conversation starters.
Having a long list of solid deep questions to ask is the first step. We've done the hard part for you. Now, it's up to you to make those questions blossom into fascinating, engaging conversations.
Take these questions to ask seriously. If someone opens up to you, it's a privilege and a learning opportunity.
Be open-minded, empathetic, and understanding. Try to understand the other person's perspective and not be afraid to shift your beliefs and views, even if they're deep-rooted. Above all, listen. If you're going to ask a deep question, you must give the other person plenty of breathing room to provide a well-thought-out answer.
Answering deep questions can be a little scary. Be a respectful and attentive listener, and you can be sure your company will be appreciative.
One of the greatest discoveries a man makes, one of his great surprises, is to find he can do what he was afraid he couldn’t do.
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