77 Deep Questions to Ask - Best Way To Know Them Deeper Quickly

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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.

Contents

The Best Deep Conversation Topics

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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

8 Best Deep Conversation Starters

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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:

1. Would you rather live 120 years comfortable but dull, or live half as long but have an exciting adventure-packed life?

What's better – a long life or a well-lived one? This conversation starter can lead to inspiring conversations. Plan an adventure now!

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2. Would you sacrifice yourself for a stranger?

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?

3. What's the most memorable lesson you learned from your parents?

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.

4. How have your priorities changed over time?

Yesterday's dreams aren't always today's reality. What drives you now, compared to last year or even ten or twenty years ago.

5. What memory instantly makes you smile?

This question immediately adds comforting warmness to the conversation. It can also help you to make new memories along the same lines.

6. Do you think pet peeves reflect something about a person?

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.

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7. What movie has made you into a better person?

There's always that one movie that made us want to have a better life.

8. If a genie granted you 3 wishes right now, what would you wish for?

Don't say you don't have a prepared answer for this profound but fun question!

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10 Best Deep Questions to Ask

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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:

9. What is your biggest regret in life?

This interesting question makes great conversation. This gives you a deeper connection and knowledge with who you're talking to.

10. What is the craziest thing you have done as a kid?

This sometimes presents itself as those casual questions that we can all laugh about.

11. What is your happiest memory with a loved one?

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.

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12. What is your dream job?

And how close or far are they to it?

13. What do you think are the 5 most beautiful things in the world? Why?

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.

14. What makes you feel most empowered?

Whether it's lifting weights or blocking someone on Facebook, there are moments when we feel on top of the world.

15. Which is more important: what you say or how you say it?

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?

16. Do you believe in heaven and hell?

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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17. Would you consider yourself an introvert or an extrovert?

The answer to this question says a lot about how people view themselves.

18. What is your guilty pleasure?

It's a good conversation if the other person decides they're okay with opening it up to you!

10 Best Deep Questions to Ask a Girl

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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:

19. What's your greatest accomplishment so far?

Learn about what makes her proud. Be sure to ask follow-up questions about the work she put in to get there.

20. What’s your favorite thing about yourself?

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.

21. What impression do you think you give when you first meet someone?

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.

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22. What is your idea of a healthy relationship?

There's no need to ask a relationship expert for this. Sometimes, we get insightful answers from a past relationship.

23. What is your idea of a perfect day?

Maybe you can help them achieve that perfect day.

24. Do you believe in love at first sight?

Whether they do or don't, you'll get to know them on a deeper level.

25. What gets you in a bad mood?

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.

26. Do you believe in second chances?

And if they don't, would they be okay with not getting a second chance?

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27. What is a relationship deal-breaker for you?

We all have that one thing that just ruins everything, no matter how perfect the other person might seem.

28. How would you describe your last relationship?

Sometimes, challenging them to describe it in just a word makes the question a more fun conversation topic.

10 Best Deep Questions to Ask a Guy

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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:

29. When was the last time you really pushed yourself to your physical limits?

Whether it was a good day at the gym or a hike up a mountain, physical exertion usually comes with an exciting story.

30. When in your life have you been humbled?

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.

31. Who is your hero? What qualities make them your choice?

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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32. What values do you think are critical to communicating to younger men?

How can we help tomorrow's men to succeed in all aspects of existence? What critical standards must be passed down?

33. What's the one thing that should be taught in school that isn’t?

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?

34. Do you think artificial intelligence will end up benefiting, harming, or destroying humanity?

It's impossible to predict what the future will hold, but it's certainly interesting to talk about.

35. What bad habits have you already stopped?

There's always something to be proud of. Stopping a bad habit is an achievement.

36. Who was your role model in life?

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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37. Do you believe everyone has a talent?

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.

38. What kind of parent do you wish your kids remember you?

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.

8 Best Deep Questions to Ask a Girlfriend

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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:

39. Have you ever lost someone close to you?

This question can be difficult. If she doesn't want to talk about it, be an understanding boyfriend and change the topic.

40. Is there anything you’re ashamed of from your past?

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.

41. What were your family's views on race, ethnicity, and difference?

Learning about her family helps you to understand her better.

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42. Other than me, who in your life do you wish you’d met sooner?

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.

43. What is your love language?

It's an essential and good question to ask if you want to treat them right and know them deeper.

44. How important is intimacy in a relationship?

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.

45. What have you learned from your past relationships?

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.

46. Is it possible to stay friends with your exes?

Not everyone can agree on one answer. The topic is always up for debate.

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7 Best Philosophical Questions

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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:

47. How important is freedom of speech in a healthy society?

Is there a limit to what should be allowed? Do they think being able to say anything is more beneficial or harmful?

48. Is it possible to be too creative to the point of insanity?

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?

49. Do dreams have meanings?

Or are they just neurons firing arbitrarily? Are our brains trying to tell us something?

50. Which is more real – mind or matter?

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?

51. What do we most need in this world?

Beyond the apparent air, water, shelter, and food, what do we really require to make it in this world?

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52. What is your biggest fear?

It's a common thought that we always want to know.

53. Do you think spirituality is important?

This will say a lot about who they are as an individual.

7 Deep questions to ask a new friend

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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:

54. How do you feel about getting older?

You'll learn about your new friend depending on whether they're afraid or excited about it and why.

55. Do you have any tattoos? What is the meaning of each tattoo you have?

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.

56. Have you ever felt like your world is falling apart?

If they say yes, be a friend and offer your time to listen to them.

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57. Do you believe in life after death?

It would also be nice to know what their concept of an afterlife is! Definitely a topic worth talking about.

58. What is the best piece of advice you have received from a friend?

Maybe you can make use of that advice, too! Whatever it is, it must be terrific and mind-blowing.

59. Did you regret giving your first kiss to someone?

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.

60. Would you choose friendship over a romantic relationship?

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.

9 Best Existential Questions

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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:

61. What is the difference between living and existing?

This question really makes you examine whether you're just passing the time until you die or making the most of every day.

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62. What are we a part of?

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.

63. Where do you think we go when we die?

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.

64. Where do you think we come from?

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?

65. Do you think a parallel universe exists?

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?

66. Do we have a greater purpose?

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?

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67. Where or what was your consciousness before you were born?

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?

68. As a human, are you an outside observer of the universe, or are you a piece of the universe observing itself?

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.

69. Is time a construct of man or a rule of nature?

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?

8 Best Deep and Thought-Provoking Questions To Ask

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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:

70. At what point is a technologically enhanced human not a human anymore?

Conversely, if you have an ax and replace its head and then replace its handle, is it still the same ax?

71. Suppose a child somehow survived and grew up in the wilderness without any human contact. How "human" would they be without the influence of society and culture?

Are we a product of our environment? Or is humanity ingrained in us?

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72. Would things get better or worse if humans focused on what was going well rather than what’s going wrong?

On a grand scale, is positive or negative reinforcement more effective for creating change?

73. Does the study of philosophy ever lead to answers or simply more questions?

Can we ever reach a final destination, or are conclusions always out of reach?

74. Does jealousy have value in driving humans to improve themselves or is it a purely negative emotion?

This question forces you to examine what's commonly viewed as a negative trait in a positive light.

75. What advice would you give your younger self?

We just hope that your younger self is someone that listens to advice from an older you.

76. If you were given a chance to play a favorite memory for the rest of your life, what would it be?

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.

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77. Why do humans need love and affection?

This philosophical question will surely get both of you thinking deeper.

Downloadable and Printable List of Conversation Starters

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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Frequently Asked Questions

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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.

Is it okay to ask deep questions to a new friend?

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!

What are the benefits of asking deep questions?

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.

How do I know if I'm asking the right questions that will let me know her better as a person?

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.

How to Start a Deep Conversation: 5 Tips

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Starting a conversation can seem intimidating, but as long as you follow these tips, you'll be good to go.

Tip #1: Know your company

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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.

Tip #2: The setting matters

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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.

Tip #3: Pay attention to body language

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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.

Tip #4: Use deep questions sparingly

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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.

Tip #5: Participate in the conversation

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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.

Looking for More Deep, Personal Questions to Ask?

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.

1. These straightforward get to know you questions help you to connect with someone. They're incredibly versatile, perfect when you're just starting to get to know somebody.
2. When you just want some fun and laughs, nothing beats would you rather questions. It's a timeless game that never gets old.
3. Whether you need something to talk about at dinner or you want to pass the time on a long car ride, these questions for couples are sure to spark some interesting discussions.

In Conclusion

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.