Sam Whittaker | Oct 13, 2020 | 0
121 Deep Questions to Ask – Spark deep, personal conversations.
New? Start here. | This post contains affiliate links. That means that we receive a commission for purchases made on them (more info).
Deep questions to ask are truly powerful.
…Because, not only do these questions tell you a ton about a person, but these questions are (obviously) designed to start a deep conversation (and these can literally bond people for life).
Whether you’re having drinks with the boys or connecting with a girl on a dinner date, personal conversations help you to genuinely understand each other in a profound way.
While heavy discussions can be intense, they’re incredibly rewarding. You can learn a lot about the other person, but you can also learn a great deal about yourself.
Deep conversations give us perspective. They help us to understand our fellow humans who inhabit this planet. They allow us to form connections that you simply can’t get through light-hearted chatter.
There’s nothing wrong with small talk, but there’s a time and place for big talk.
Be prepared to go on a journey through the heart, soul, and mind. We’re going to help you to open doors and build relationships. Don’t rush into these. Many of them are powerful questions that demand respect.
Are you ready to go into deeper territories?
Okay, now that you have a good idea of how to approach 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 a conversation may go.
Take these topics, and use them to form your own unique questions that are catered directly to your company.
Here are some of the best deep conversation topics:
Goals and Aspirations
These deep conversation starters act as starting points. Many of them are open-ended and can lead virtually anywhere.
If you’re not prepared for a potentially lengthy discussion, you may want to use some of our other deep questions to ask.
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 will surely give you something to begin with?
Here are 15 of the best deep conversation starters:
1. If you could ask a single person one question, and they had to answer truthfully, who and what would you ask?
This is a huge question with endless possibilities. If you want to make it even tougher, change it to ‘anyone dead or alive.’
2. Would you rather live 120 years that are comfortable but boring, or live half as long, but have an exciting adventure packed life?
What’s better — a long life or a life well-lived? This conversation starter can lead to inspiring conversations. Plan an adventure now!
3. What’s something that overwhelms you?
We all get overcome by life from time to time. What really makes you stop in your tracks?
4. What do you take for granted?
This question can help both people recognize their blessings and appreciate them more.
5. 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?
6. What’s the most memorable lesson you learned from your parents?
What’s that life lesson that has stuck with you all these years? This is a great opportunity for you to learn a thing or two, so pay attention to the answer.
7. 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.
8. What does your ideal life look like?
If you could design the perfect life, what would it entail? This conversation really lets you see the other person’s true priorities.
9. What was the greatest day of your life?
This is another question that can inspire you both to seek out ways to top that day.
10. Would you rather be crazy rich, or deeply in love?
And can money buy love? What’s more important in this life: physical wealth or internal happiness?
11. What has been your biggest challenge in life, and how did you overcome it?
This conversation can be a tough one for some folks to answer, so be sensitive if they don’t want to answer.
12. What obstacles are you currently trying to overcome?
This is a chance for someone to open up about difficulties they’re going through right now. Do your best to help them to push past them.
13. What are you most proud of?
There’s nothing wrong with bragging a bit. What has been their crowning achievement up to this point?
14. 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.
15. If you had to get a tattoo right now, what would it be?
This conversation can be pure fun, but it can also tell you a lot about the other person.
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 15 of the best deep questions to ask:
16. Are you living a meaningful life?
This one cuts straight to the point? If not, why? If so, how?
17. What’s the one thing you cannot live without?
Whether it’s their favorite ice cream or a family member, this question lets you know what really matters most.
18. When is it acceptable, if ever, to disobey the law?
Is there a gray line, or is the law black and white?
19. What do you want your final words to be?
This is a great question because the resulting conversation can be simultaneously funny and serious.
20. What inspires you the most?
We all have reasons for doing what we do. Where, who, or what do they draw their inspiration from?
21. 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.
22. 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.
23. Which is more important: what you say or how you say it?
Words can take on different meanings depending on context, inflection, facial expressions, body language, and other countless factors. Is the content what matters, or how the content is portrayed?
24. 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?
25. Do you live to work or work to live?
Do you push hard so that you can enjoy the finer things in life? Or is your drive just part of who you are?
26. Do you trust anyone with your life?
Being trusted with someone’s life is a big deal. Has anyone earned that position in their life?
27. Would you consider yourself an introvert or an extrovert?
The answer to this question says a lot about how people view themselves.
28. Do you believe in true love?
If not, do you think you ever will?
29. How do you think the world will change in 10 years? 50? 100?
It’s fun to speculate about what the future may hold. The conversation can take many forms, from lighthearted and imaginative, to downright terrifying.
30. If you had the option to know the date and circumstance of your death, would you?
It would undoubtedly affect the rest of your life, but for better or worse?
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 tough. Having heartfelt questions to ask a girl shows that you truly care about her beyond a superficial level. It proves that you value what’s inside.
Here are 15 of the best deep questions to ask a girl:
31. 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.
32. What’s your favorite thing about yourself?
This question helps you to understand her best traits, while also letting her brag a bit. It opens up plenty of opportunities for you to compliment her too.
33. What is something you are certain you’ll never experience?
What just isn’t in the cards? Is she actively avoiding those things? If so, why?
34. What impression do you try to give when you first meet someone?
Friendly? Tough? Funny? How do you want to be viewed?
35. 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.
36. What do you think your worst trait is?
There’s nothing wrong with acknowledging your faults. In fact, it can help you to overcome them.
37. How would your perfect partner treat you?
If you’re pursuing her romantically, now is the time to take out your notebook and pen.
38. What’s something you enjoy doing that you never get tired of?
This question is similar to asking about her hobbies, but it really cuts to the chase.
39. What one responsibility do you most wish you didn’t have?
We all have things in life we have to handle. Maybe the two of you can share the load.
40. What something that you’re embarrassed you’re so good at?
What are her secret talents? If she’s willing to teach, you might just learn something new.
41. What are you excessively obsessive-compulsive about?
We all have eccentricities that make us unique. What drives her up the wall?
42. What’s the nicest thing you’ve ever done for another person?
This question lets you know how compassionate and caring she is (or isn’t).
43. What do you think about most often?
This is a direct question that helps you to understand what’s going on in that brain of hers.
44. How do you recharge?
Whether it’s napping, yoga, or a couple pots of coffee, we all have our methods to overcome exhaustion.
45. What happened in the last dream you remember?
This question can lead to hilariously bizarre or deeply meaningful responses.
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 important 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 15 of the best deep questions to ask a guy:
46. What does honor mean to you?
Is it something you earn, or should it be given freely?
47. 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 interesting story.
48. What’s the thing you most want to achieve before you die?
We all have our bucket lists. What are his must-dos?
49. Is intelligence or wisdom more useful?
Would he rather have a brain full of facts or an inherent knowledge of the world and how to react to it?
50. What’s something that offends you?
At what point does something cross his line?
51. 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.
52. 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.
53. What values do you think are critical to communicate to younger men?
How can we help tomorrow’s men to succeed in all aspects of life? What critical standards must be passed down?
54. Would you sacrifice your life for someone?
Would you put yourself in harm’s way if you knew the other person would survive? Would it have to be a friend or family member, or would he do it for a stranger?
55. What part of your culture are you most/least proud of?
Culture can be a beautiful thing, but sometimes it may make you cringe.
56. 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?
57. What makes you most angry about our country?
We all like to play armchair president. What would he change?
58. Who is the most powerful person alive today, and why?
Who is the one person who wields the most power? Is it a political figure? A scientist? A multi-billionaire?
59. What is the most unsettling fact that you can think of?
What fact instantly makes you shudder? You may want to have some lighthearted questions on deck to bleach your brains after this one.
60. 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.
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 15 of the best deep questions to ask a girlfriend:
61. Have you ever lost someone close to you?
This question can be difficult. If she doesn’t want to talk about it, be understanding and change the topic.
62. What bridges are you happy you burned?
Sometimes you have to make necessary changes for your own best interest.
63. Is there anything you’re ashamed of from your past?
Everyone makes mistakes. Is she willing to talk about them? It may help her to open up if you talk about your past errors first,
64. What is the most insensitive thing a person can do?
Be sure to take note of her responses, and never, ever do them
65. What are you most determined to do in your life?
What is that one goal she’s focusing on? Try to help her to achieve it.
66. What makes you most uncomfortable?
Again, take note and avoid at all costs.
67. What were your family’s views on race, ethnicity, and difference?
Learning about her family helps you to understand her better.
68. When do you feel the most confident?
What are those moments when she just knows that she’s on?
69. Is there anything you’re obsessive-compulsive about?
We all have our habits and ticks. Does she have anything that makes her just a little crazy?
70. 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 that person brings to her life.
71. Is there anyone who has completely lost your respect?
Learning about those who have let her down can help to prevent you from doing the same.
72. At what point in your life were you most happy?
Be inspired by her response, and try to create similar moments that you can share together.
73. Do you want to be a parent someday?
This question can lead to some more serious discussions about the future, so use it cautiously.
74. Have you ever broken someone’s heart?
If she has, that doesn’t necessarily mean she’ll break yours. That said, it never hurts to be aware of warning signs.
75. What was your favorite activity as a child?
This conversation is fun and lighthearted, but it also helps you to better understand the person that she is today.
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 15 of the best philosophical questions to ask:
76. Can a society exist without laws?
This question simultaneously tells you how they feel about humanity and society as a whole.
77. 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?
78. Can war ever be just?
Are wars necessary for the progression of humanity? Or are they obstacles holding us back?
79. Can animals reason?
If yes, can they think of any examples?
80. How much longer will humans dominate the world?
Is our destruction nigh? Or are we going to be the top of the food chain forever?
81. Is privacy a right?
As the world grows increasingly digital, this question is going to become more and more relevant.
82. Is love just a feeling?
Or is it something more powerful and intangible than that?
83. Is it worse to fail or never try at all?
Is a blemished record more shameful than no record at all? Why?
84. 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?
85. Is there such a thing as a necessary evil or a white lie?
If doing harm results in positive net results, is that harm actually good? Do the needs of the many outweigh those of the few?
86. Is it immoral to do something wrong if nobody ever finds out?
If a tree falls in the woods, and there’s nobody there to hear it, but you chopped it down, is it wrong?
87. Is it better to have loved and lost or to never have loved at all?
Is the dismay of heartbreak worth the glory of love? Can you find true love twice?
88. Do dreams have meanings?
Or are they just neurons firing arbitrarily? Are our brains trying to tell us something?
89. 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?
90. What do we most need in this world?
Beyond the obvious air, water, shelter, and food, what do we really require to make it in this life?
Getting to know a new friend isn’t always fun and games. Sometimes, you have to bring out the deep questions to ask a new friend in order to have more extensive knowledge of your friend.
Here are 8 deep questions to ask a new friend:
91. Have you ever saved someone’s life?
Hands down to them if they did. What could be nobler than saving someone’s life?
92. Do you think people are basically bad or basically good?
Nothing but a good philosophical question to get the things going for deeper questions.
93. How do you feel about getting older?
You’ll gain knowledge about your new friend depending on whether they’re afraid or excited about it and why.
94. 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. Sometimes, we just think it’s cute.
95. 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.
96. Do you ever wish you were born in another decade?
Sometimes, you just know you don’t belong to this generation.
97. Do you enjoy the slow, seemingly empty moments in life?
There’s beauty in the things we think are just nothing.
98. 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.
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 15 of the best existential questions to ask:
99. If you could watch everything that happened in your life until now, would you enjoy it?
Why or why not? You may not be able to change the past, but you can still create a positive future.
100. Do you think immortality is possible?
Our atoms will eventually rearrange and form something else — does that mean we exist forever? Can our consciousness be simulated eternally in multiple universes?
101. What is the difference between living and existing?
This question really makes you examine whether you’re just passing time until you die or making the most of every day.
102. 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 think about life as a whole. Then the possibility of other lives in other universes. Keep going bigger until it hurts.
103. 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.
104. 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 in order for the universe to be truly infinite? Are we part of a simulation? What is the origin of the human species?
105. How do you know you are not dreaming right now?
Pinch yourself. Did it work?
106. 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?
107. What is the meaning of life?
Or is there one at all? Is there a grand answer or is it all just chaos?
108. 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?
109. 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?
110. 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.
111. Did the human brain name itself consciously?
Someone used their brain to call a brain a brain. Did the brain just like how that word sounded?
112. If all of your molecules are deconstructed, teleported to the other side of the Earth, and reconstructed, were you killed and recreated, are you a clone, or are you still the same person?
Similarly, if you have a car, and then you replace every single piece one-by-one with identical components, is it still the same car?
113. 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?
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, it’s important that you 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:
114. At what point is a technologically enhanced human not a human anymore?
Conversely: If you have an ax, and you replace its head and then replace its handle, is it still the same ax?
115. If 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?
116. 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?
117. 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?
118. What is the best way to train people to see the gradients in the world around them instead of just a simplistic “this is good, that is wrong” view of the world?
Critical thinking is difficult to teach.
119. Why don’t we as a species take more advantage of the fact that we have almost infinite knowledge available to us?
Are we selling ourselves short?
120. Is a life that focuses on avoiding pain and seeking out pleasure a good and worthwhile life? Why or why not?
Is it wrong to follow our most basic instincts?
121. Does jealously 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.
Tip #1: Know your company
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 conversation with them, and also that they’re equally as comfortable with you.
Tip #2: The setting matters
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
If the person 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
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
One of the biggest mistakes you can make is keeping the conversation one-sided. If you want a person 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.
Downloadable and Printable List of Conversation Starters
Here is a downloadable and printable list of deep questions to ask (right click the image and select Save Image As…):
Looking for More Deep, Personal Questions to Ask?
By now, you should be a bona fide deep thinker. After a few heavy conversations, you might feel lie 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.
Here are some more awesome questions to ask:
- These straightforward get to know you questions help you to connect with someone. They’re extremely versatile, perfect when you’re just starting to get to know somebody.
- When you just want some fun and laughs, nothing beats would you rather questions. It’s a timeless game that never gets old.
- 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.
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 don’t 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, it’s crucial that you 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.