Deep Questions

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?

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.

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?

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?

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?

Do You Believe In True Love?

If not, do you think you ever will?

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.

When Is It Acceptable, If Ever, To Disobey The Law?

Is there a gray line, or is the law black and white?

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?

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.

Would You Consider Yourself An Introvert Or An Extrovert?

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

What Are You Most Proud Of?

There's nothing wrong with bragging a bit. What has been their crowning achievement up to this point?

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.

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.

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.

What Do You Want Your Final Words To Be?

This is a great question because the resulting conversation can be simultaneously funny and serious.

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.'

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.

Are You Living A Meaningful Life?

This one cuts straight to the point? If not, why? If so, how?

What Do You Take For Granted?

This question can help both people recognize their blessings and appreciate them more.

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.

What's Something That Overwhelms You?

We all get overcome by life from time to time. What really makes you stop in your tracks?

What Inspires You The Most?

We all have reasons for doing what we do. Where, who, or what do they draw their inspiration from?

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!

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.

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?

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.

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.

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?

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.