Simple Questions That Can Lead to Deep Conversations

Everyone needs to have deep honest conversations

If I asked you a couple of very simple questions about you, do you think you could answer them for me?

What could be so difficult about it?

Imagine we’re sitting in an empty room in front of each other. We are strangers. I don’t know anything about you but I’m interested in what you’re like.

How do you get to know someone? You ask questions and observe them. Nobody starts with existential stuff, you don’t want to scare your opponent.

Oh, yes, we’re opponents now. We’re competing who knows themselves best.

Let’s have a warm-up round.

Tell Me What Is Your Favorite Color

I know, I know, we’re not in a kindergarten. But colors are beautiful and there are a lot of them. It must be difficult to choose only one of them as your favorite. Shouldn’t your favorite color tell something about you then?

So what’s your answer? Blue? Is that even a color? Well, of course, it is but it doesn’t say much. There are more shades of blue that one can count or imagine. I want to know the deeper stuff.

If you close your eyes and think of that beautiful color blue, what do you see?

Is it the sea? Is it calm or is it scary? Is it the blue that others think it’s green? Seafoam green? See, it’s not even blue that you like. Can you feel the wind? What does it smell like? How do you feel?

Oh, it’s the sky? The clear sky on a warm summer day? The sky before a storm with heavy dark magnificent clouds? Or is it the clear sky at night where you can see the milky way?

The blue like your favorite childhood blanket? Now we’re talking. Tell me more.

I like green

The green that our old family wired phone was.

The same green as my father’s uniform.

The green my poor plant turned after I fertilized it. It’s more alive now.

The green that smells like grandma’s garden ant tastes like those weird blackberries on a bush.

The green of the dress my grandma sewed for her burial. She’s still alive though.

If nostalgia was a color, it would be this green for me.

It was the phone I used to pick up when I was three. It was my favorite thing in the whole house. My father was a policeman back then and he was a happier man when he wore his uniform. My mother gave me this plant for my first apartment. It’s a symbol of my independent life. My grandma still lived at her farmstead. She’s been ready to die since she was 40. She’s 84 now.

So tell me about your favorite color. Maybe it’s not that silly.

What Is the Book That Changed Your Life?

Is this question more sophisticated for your taste? It’s not an easy one though.

Books can change people for better or for worse. I hope yours had a positive influence.

Is it a children's book? The first you read after you mastered the art of reading? It’s a big deal, I understand. Your life was changed for sure when you learned to read. But let’s dig deeper.

It’s The Little Prince? You know, I haven’t read that book and I really don’t know what’s all the hype about. Pick something different.

Harry Potter? Your childhood was dull and those books brought some magic into it? I understand, books are magic.

Anything since you were a grown-up? Self-help, poetry, classical literature? Have you had an epiphany after finishing a book or smirking all the way through it? I’m sure I have.

A poetry book

I used to think poetry was lame until I read a good poetry book. This collection of poems opened my eyes to the beauty of language, the use of words, and expressing emotion through writing.

I started writing poems myself. Even if they’re not great, I am very proud of them. A poetry book was a bridge to my self-discovery. It showed me the world in a different light.

The Fall by Albert Camus

It’s my favorite book I’ve ever read. I was smirking through it because I related to the main character so much and he was very flawed. This book called me out. It felt like a very honest conversation. I needed that.

Albert Camus introduced me to existentialism. Then I found out I might be a nihilist. A positive nihilist at least.

The Millionaire Fastlane by MJ DeMarco

It seems like a misfit in here but it truly changed my life. Nobody ever talked to me about money and career rationally. It was always beliefs based on the experience the person had and rumors they’ve heard.

Some say to save everything up, some say to spend, nobody can tell how to actually earn good money, people irrationally hate all businessmen. I had a mess of an understanding about money and life.

I was so skeptical about reading a book with this loud title from a “greedy millionaire”. What a dumb ass I was. But I can say I am not that anymore.

Are books not personal enough for you? Are you not a reader? Okay, let’s dig deeper.

What Is Your Biggest Regret in Life?

I’m bringing the big guns. You might want to seem like you have your shit together. You want strangers to think you’re cool and confident. You want to seem almost perfect. Living your best life with all the right decisions.

I’m not interested in that. Tell me the real deal. Be honest. Be vulnerable.

Don’t paint a picture of your life, show me a photograph.

Tell me how you got married out of convenience. How you never wanted children but your parents pushed you and you gave in.

Tell me how you feel like a failure for not standing for yourself.

Tell me how you don’t know who you are. Tell me your regrets for not paying attention to your thoughts and feelings.

Tell me how you’re just a shell of a person, living by default and not taking risks.

I can tell you almost all that about myself.

I feel like a failure but I don’t have to

My biggest regret in life is not standing my ground when I needed to. I gave up my dreams to please everyone around me.

I tried so hard to be what others expected of me, I forgot to ask myself what I’d like to do, who I’d like to be.

I don’t even have my own dreams. I feel like I don’t know myself. Everything I do is because society tells me to, I’m not sure much comes from within.

I love getting to know other people and I can’t stand to be asked questions about myself. I don’t know the answers and it bothers me.

I regret not having honest conversations with myself.

Defining your regrets can be comforting. If you know what your regrets are, you can act on them. You can have all the honest conversations you need and figure things out.

Do you regret not exercising? Great, you can start now. Do you wish you’ve read more books? I hope you’re on the way to the library already. Do you want your parents to know how you feel about them pressuring you? I hope you’re writing them a letter explaining everything.

Your regrets don’t define you. What you do with this information does.

What Makes You YOU?

This is the most difficult question, right? Not at all. I can answer it for you.

You are everything you like, dislike, love, appreciate, believe, do, think and feel. You are your favorite color, your most precious memory, all the honest conversations, favorite books, people you’ve befriended, and regrets you’ve had.

You are a unique collection of experiences. You are the sandwich that you make every morning. You are the smile you give to a dog on the street.

You are the shell and the core of a human being.

You are YOU and only you know what it means. So tell us about it. Let people know you, let yourself know you.

Life would be better if we had more honest conversations. If we told the truth, dug deeper, weren’t afraid to seem lame for making mistakes. If we talked loudly about our mistakes and regrets, we’d have fewer secrets. We’d be free of judgment.

I want to know you. I want to have an honest conversation with you. This way we can get to know each other and ourselves better. We should be more honest and less judgmental. Our conversations would bring way more pleasure and value into our lives.

It was nice to meet you. I honestly enjoyed our talk.

Next time you meet a stranger or even a person you know very well, ask some simple questions and dig deep. Trust them and let them trust you. Answer honestly and listen without judgment.

Have an honest conversation, everyone could use one.