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Deep questions are where all of the good conversations are hiding. No one looks forward to fluffy discussions about nothing. To get to people or even yourself on a new level, you need to ask deep questions that provoke thought. 

Too many people think knowing someone knows their favorite color or what they watch on Netflix. That information is helpful, but they don't help you to understand another person's perspective. When you ask the right deep questions, it gives you insight into what another person has been through and how that influences their choices. 

There are times and places for small talk, but if you want your relationships to grow, you have to move into BIG TALK. When you get to understand people, you begin to break down walls people built and pull back the layers to their mind. 

"Onions have layers. Orges have layers. Onions have layers. You get it? We both have layers" - Shrek 

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Contents of Deep Questions

12 Deep Questions to Get Great Conversations Started 

These are not your average conversations starters. The goal is not basic small talk, but to ask questions that surprise people and make them think for a second. Do you want to be forgotten to ask, "how are you?" or remembered for being the person who asked deeper and intentional questions? The answer is easy.


1. Would You Rather Live 120 Years That Are Comfortable But Boring, Or Live Half As Long, But Have An Exciting Adventure Packed Life?

Asking this question will give you insight into the risks someone is willing to take. People who play it safe like the idea of comfort and being in control of outcomes. People willing to take more risks like to feel like they are moving forward quickly, and they want to have more experiences in their life, even if they die younger. 


2, What’s Something That Overwhelms You?

You don't know someone until you understand what things they are easily overwhelmed by. Ill never forget the first time I watched my wife do taxes and burst into tears. For some reason taxes are too much for her and that was the last time she had to think about them because I took them off of her plate. Everyone is overwhelmed by something no matter how irrational it may be. 


3. How Do You Deal With Stress

When you become overwhelmed by things, what is your response. Some people sleep, some work, some clean, some eat junk food! This question is great because a lot of people have never thought about how they respond to stress. 


4. Would You Sacrifice Yourself For A Stranger?

Here is a great question to help you get insight if you want to associate yourself with caring people. The key is not if they say yes or no, but its why they say yes or no that will reveal a lot.


5. What’s The Most Memorable Lesson You Learned From Your Parents?

This question kills two birds with one stone. The first thing it will do is help you identify their relationship with their parents. Do they come from a single-parent household? Do they adore their parents, were they adopted? The second thing this question will do is show you what their most significant takeaway is from how they were raised.


6. What Does Your Ideal Life Look Like?

When you understand what someone's ideal life looks like, you know what they aspire to have. Where people's treasure is, their heart will also be. Make sure you listen and only talk to ask clarifying questions.


7. What is Your Most Cherished Accomplishment?

Gain insight into what someone has done with their life. This question will tend to make someone light up, but it may show that someone is very hard on themselves if it doesn't.


8. What Obstacles Are You Trying to Defeat? 

We all have obstacles, and when you know what other people are struggling with, you can identify an area that you can be of immediate assistance. There is no better way to build a bond with someone than to help them with something.


9. What Memory Makes You Smile the Hardest?

This another question that is interesting because it will show you what area of their life they go to. Do they talk about something they did, do they talk about family, do they bring up a team? 


10. If You Had to Get a Tattoo Right Now What Would You Get?

Tattoos are permanent, so something matters enough to get a tattoo of it says a lot. They may hate this question because they hate tattoos, and that means something about people as well.


11. What Made You Choose Your Line of Work? 

Too many people ask what do you do for a living and its a boring question. A much better question gets to the root of why they do what they do. Most people are not expecting this question either. 


12. If You Could Have One Superpower?

This question is clearly not based on reality so it makes it a more fun question to ask. When you know what someone wants to amplify, it can give you insight into a short coming they may have, or just show you what is important to them. 

10 Great Questions for Self Reflection 

These are questions that you ask yourself, but you should be weary of asking others these questions. Some of these questions could come off as rude, or make others feel like you think you know it all, or have it all figured out. 


1. Are You Living a Life That Matters 

You can't fake your way around this question. If you are living a life that matters you have to have proof of that. If you are not living a life that matters, today is the day you change that. 


2. What Can You Not Live Without?

This questions points to how important things are in your life. Everyone has a material item that they can't live without. When you point it out it says something about what you value. 


3. Who Cannot Live Without You?

If a lot of people can't live without you, it could be a sign that you value yourself to highly or that you are not helping people to be more independent. 


4. When is it Acceptable to Break the Law?

This questions helps you to understand where you are morally, and why. 


5. What Inspires You the Most? 

If you know something inspires you a lot, what can you do to experience it and be around that more? You will produce more of your best self when you're inspired. 


6. What Happens After You Die? 

It does not matter if you are religious or not, this question helps you to reflect on if you are preparing for the after life, or whether it matters or not. 


7. Do You Live to Work Or Work to Live?

First, you have to decide which side of this equation you want to be on. Secondly, do whatever it takes to move yourself closer to that side. 


8. Who Do You Trust With Your Life?

Asking this question will hit you in two different ways. It will help you see who really has your back. Secondly, it will make you think about how trustworthy of a person that you have been. 


9. Are You Introverted or Extroverted and Are You Staying True to Who You Are?

If you're an introvert or an extrovert, it can be easy to lose yourself, and try and be the opposite. The only way to be happy is to be true to who you are. 


10. What Do You Want Be Remembered For?

If you live a life of impact you will be remembered for doing so. This question will help you think of what you want in the end, and how you can get closer to that life. 

Deep Questions

14 Deep Question for Your Potential Significant Other 

These questions are great to ask when thinking about making a relationship you have more serious. These questions are not first date questions. You should already have some rapport and trust built. 


1. What is Your Favorite Thing About Yourself? 

Knowing what people love about themselves is important. It's an area you can praise them but it also helps you see how self-aware they are. 


2. What is Something That You Know You Will Never Have to Experience?

Never is a strong word. There is so much that this question can reveal about privilege, confidence and many other traits. 


3. What Do You Think Your Worst Trait Is? 

Giving someone the opportunity to talk about where they lack confidence, or what they don't like can reveal insecurities, and places that you can help to build them up. 


4. How Would Your Perfect Partner Treat You? 

Everyone has a vision for their ideal relationship. Its important you understand what that is, because it may be unrealistic, and you may have no chance of living up to it. 


5. What Are Your Top Three Most Important Things in Life? 

Everyone has priorities. With these question you want to get to the heart of their priorities, and it should not be the list that just sounds good. 


6. What One Responsibility Do You Wish You Didn't Have? 

This is a tricky question because it helps you to learn what responsibilities may be put on your shoulders in the future. For example, if someone answers dishes, that could mean that in the future that will be seen as your responsibility. 


7. What is Something That Offends You? 

You want to make sure you know the answer to this because there is no way to end a relationship faster than pushing the wrong button. 


8. What in Life Has Humbled You the Most? 

What has this person been through that has taken them down a few levels. They may need reminding of this humbling moment. 


9. What Part of Your Culture Are You Most and Least Proud Of? 

Understanding your own culture is important, but in a relationship its important to understand the cultural implication of someone who you may be in a relationship with. 


10. What Makes You Proud/Angry About Our Country?

National politics can cause so many heated debates. You will want to know where this person stands, and measure those views against your own. 


11. What Bridges Are You Happy You Burned?

This will reveal a bit more about what they have been through, so you can understand them on a deeper level.


12. Have You Ever Lost Someone Close to You? 

One of the deeper questions on the list but one that can provide so much insight, and understanding of a another person. 


13. What Were Your Favorite Things to Do as a Child?

Whether you want to admit it or not, we all still have that little kid in us somewhere, but we may just struggle to bring that side out. The better you understand that little kid the more you understand that person. 


14. Have You Ever Broken Someones Heart? 

Here is a chance to just listen, and ask clarifying questions because this one can go in so many different directions. 

10 Philosophical Questions 

These questions don't have a right or wrong answer, and you can ask anyone these questions as long as they enjoy having deeper conversations. 


1. How Important is Freedom of Speech for a Healthy Society?

This question could reveal different cultural truths, and address ideas on oppression and how widespread it is. 


2. Can a Society Exist Without Laws and Punishment? 

An argument can be made either way, but what you need to look for here is the reasons why. 


3. Will Humans Continue to Have Dominion Over The Earth ?

Why will humans dominate, and if they don't then who will, and how do you come to that conclusion? 


4. Is Privacy a Right Everyone Should Have? 

In today's world of companies like Google and Facebook, and governments around the world pushing the privacy boundaries, its telling to know where people stand with this topic. 


5. Is Love a Choice or a Feeling?

Do people feel their way to love or is it something you decide on. Which one produces longer lasting marriages? 


6. Is it Worse to Fail or Never Try at All? 

This question will reveal what people think about effort, and how important it is. 


7. Can You Ever Empty Your Mind and Think of Nothing? 

Mindfulness and meditation have grown a lot over the last decade, but not everyone is buying it. 


8. Do You Believe That Sometimes Evil is Needed? 

Don't ask this question unless you are ready to go into some heated debates. 


9. Do Dreams Have Meaning to Our Real Life? 

A light question that you can ask anyone, and get amazing insights into their thoughts. 


10. Do We Need More Optimists or Pessimists?

A great question to ask if you feel strongly either way.


Deep Questions Life

10 Deep Questions About Life and Existence 

These are questions to get you thinking about life and what we are even doing here. They are fun questions that you can ask anyone to get them thinking about the bigger picture. 


1. If You Watched a Film of Your Whole Life Until Now, Would You Enjoy It?

There is so much revelation in this one question. It makes you reflect on what you have done and how you have managed to exist. Then, it makes you dig deep on whether you should be proud of it. 


2. What is The Difference Between Living and Existing? 

Like the last question, this question forces one to reflect, but also to make a decision on how one wants to live moving forward. 


3. Where Do You Think We Come From? 

Is it evolution? Do you believe in God, and Adam and Eve? The question is a deep one and can lead to a plethora of other questions. 


4. Is There Life In Other Universes? 

Are we here alone or is there much more out there than we know of? Questions about the universe remind us of how small and insignificant that we are. 


5. What is The Purpose of Life?

Another question that can lead to asking a hundred more questions. Life can have so many different meanings too so many different people, and this question will reveal where someones heart is, in the moment. 


6. Did Humans Create Time or Did Nature?

The answer may not matter but the question is deep none the less. 


7. When Does Technology Stop Helping Humans? 

How close are we to the point where technology overtakes humans, and causes us more problems then we intended. 


8. If a Human Grew Up Like Tarzan in the Wilderness Would They Still Be Human? 

The question makes you think deeply about how much of your humanness is from your parents vs your nature. 


9. Should Society Focus More On What is Going Right vs What is Going Wrong? 

The question points to whether we need to be optimists or pessimists. The question starts with the big picture, but will make you think about how you play a role as an individual. 


10. Why Don't Humans Take Advantage of All That We Can Learn Around Us? 

Why are we limiting ourselves? The opportunity to learn is abundant, but the will is just not there, but why? 


Conclusion of All These Deep Questions

Deep questions are a great way to build rapport and understand people better. The memorable conversations in our lives are never from small talk. The great conversations come from having deeper conversations and discussing things that matter. 

Ian Warner

About the author

I went from a broken leg to a 2012 Olympian. I have spent the last 15 years building positive habits as a track athlete and entrepreneur. I founded Habit Stacker and dedicated my life to helping people to develop winning habits. I have helped over 5,000 people...

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