When nightfall comes after a long day, many of our brains make that shift from short term worries to long term ones. Our thoughts drift from "What am I going to eat for breakfast tomorrow?" to "Where will I be in 10 years?" It goes from, "I wonder if I have any shampoo left," to "Do I want kids someday?"

Having a partner to bounce these thoughts off of is an amazing luxury that should not go under appreciated. We can finally talk about the meta ideas that typically elude us as we go through the ho hum cycle of daily life. If we thought about these grandiose ideas at work or school, we’d never get anything done. You can’t eat a pot pie AND think about your small occupancy in a seemingly infinite universe. You'd lose your appetite.

In my 21 short years I’ve had a plethora of what I consider to be “deep conservations," but the problem is I’ve weighted them all equally.

There’s no way this is possible considering some have been longer, more profound and more intimate than others. I've had deep conversations on the bus last ten minutes and deep conversations at a friends house go through the night.

It's because of this false equivalency that I’ve decided to to create the 5 levels of deep conversation. For each level I’ve designated topics of discussion that correspond appropriately with 1 consisting of the most shallow/easiest topics to engage in and 5 being the deepest/most difficult topics to engage in. Due to the nature of deep conversations, we don’t always climb the ladder in linear fashion, so when calculating your depth, don’t be alarmed if you “skip” a level.

At the end of the day, if you feel you’ve adequately covered a certain topic, then you can cross it off the list regardless of what I say. This isn’t the holy grail. It's merely a compass to guide you into adequately quantifying your experiences. I’m aware that these aren’t the only topics for deep conversation, but I believe they cover most of the bases.

Level 1

These are the most rudimentary subjects of deep conversation, thereby making them the most common entry points. You’ve just arrived at the cocktail party and you’re standing in a circle of strangers with a drink in your hand. Suddenly, you lock eyes with that special someone. You two start talking amongst yourselves while the rest of the circle slowly gravitates toward a different part of the room.

1.1) Relationship endeavors/shortcomings/regrets

This topic has a wide range. From romantic interests to the demise of certain friendships. We’ve all been seduced by the fruits of greener pastures ahead so everyone in the conversation can contribute a compelling personal anecdote.

Have you ever had a relationship that turned out better or worse than you thought it would? Did you lose touch with someone who you thought would always be there for you? Are most relationships inevitably doomed or is there a way to organically get it to go the distance?

1.2) Family issues/feuds/personal vendettas

It’s been scientifically proven that opening yourself up subconsciously gives others permission to do the same. No family is built perfectly and this concoction of flaws helps shape our personality whether we’re conscious of it or not.

Do you have an uncle who constantly criticizes "lazy" people but spends every night watching his old high school football games? Do you have a nemesis from elementary school who'd always go for your head during dodgeball? Do you have a strained relationship with your cousin because he still brags about beating you in arm wrestling that one time in 2006? Talk about it!

1.3) Hypothetical Harry

This is a dynamic level 1 topic because of it’s incredible range. Hypothetical Harry is essentially playing a what if/would you rather game. Creating these fictitious scenarios does three things:

1) It gives you a general feel for the person’s moral compass.
2) It tears the lid off the imagination of the conversation. Both of you can take it to unchartered territories without it seeming like an abrupt tonal shift.
3) If you time it up right, it can be the PERFECT Segway to reaching a level two or three depth. Here are some of my favorite Hypothetical Harry’s:

-If you were born in the 80s, how do you think you would have turned out differently?
-Would you rather live like a god for a year (think Bruce Almighty) then have time rewind back a year and you die? OR Just keep on living the life you have now?
-Would you rather be twice as smart as you are now? OR have an extra 8 years tacked onto your life? (I.e. if your “destiny” were to die from a meteor shower when you were 40, you’d live till 48)

Level 2

You and your special friend have drifted over to the cozy living room couch. There’s a tingling in your stomach, and you don’t know whether it’s from booze or butterflies -but it doesn’t matter. You find yourself leaning in more and more. Feeling the need to get drunk less and less. The rest of the party becomes an abstract painting. The only thing you’re focused on is your new friend’s interesting thoughts and insights. Now that you’ve built up some personal cache, you can ease right into the following topics.

2.1) Religion

Everyone has a different relationship with religion whether they practiced it growing up or not. The ONE concept you must remember is this: for some, this topic can be a land mine, and for others, it’s a walk in the park. Your JOB is to figure out which one it is as soon as possible. That way you don’t unnecessarily kill the momentum of the conversation. There’s a difference between expressing an opinion and undermining someone else’s viewpoint. The goal isn’t to persuade or be persuaded. The goal is to openly listen to other perspectives without passing judgement.

Keep in mind you’re only at level 2. There’s so much more to be talked about and it’d be a shame to let the conversation go off the rails here. If you sense the conversation going south, abort the mission and direct the attention elsewhere.

2.2) Insecurities

Like failures, talking about insecurities can be both humiliating and liberating at the same time. It allows us to be vulnerable without feeling judged. My freshman year of high school, I was so short that I used to stuff my Nike Shox with Nike socks to get half an inch taller. Nowadays I feel insecure about having boogers/morning dust on my face while riding the train to work.

I also feel anxiety over whether I'm dressed like a proper young business professional or a character from Spy Kids 3-D: Game Over. Talking about these physical and mental anxieties lifts a huge weight off your shoulders, making you feel unimpeded in the world.

2.3) Embarrassing personal stories

There’s nothing better than owning a moment in which you carried lots of shame and turning it into a funny story that you can enjoy with others in hindsight. No one is perfect and everyone's had blemishes so indulging in past poisons can often transform them into antidotes.

Maybe it was that time you accidentally accused your aunt of being pregnant. Or that time you sent yourself a bouquet of valentine’s chocolates at school, and told your buddies they were from a “secret admirer.” Those examples were completely fictitious by the way. Took me a long time to think of them. Definitely not drawing from personal experience.

Level 3

The ultimate sweet spot of deep conversations.You’ve asked your friend if they want to go out for a walk and they willingly oblige. You’ve shared some good laughs and are feeling truly at ease in your own skin. A sensation that’s eluded you for months. Your smile is comfortable and relaxed. You’re no longer self-aware about how you look or the vibes you think you’re giving off. Level 3 is all about letting go of personal issues and devoting all your attention and energy into complete immersion of the conversation. This is the over the hill moment. There’s no turning back now.

3.1) Consciousness

Consciousness is defined as the state of being awake and aware of one's surroundings. This means being in the moment and feeling the weight and power of now. Consciousness is relinquishing your worries and concerns. You’re not holding onto any past guilt or letting fear consume you. Consciousness is looking at a tree and appreciating the tree on face value. You’re not exploiting the tree for metaphor, symbolism, or inspiration. Once you can look at a tree and think of ONLY the tree, then you are experiencing true consciousness.

When do you feel most present throughout your day? Do you struggle with clarity in regards to your thoughts? Do you think meditation is beneficial or a bunch of mumbo jumbo? How often do you spend your day thinking about what to think about?

3.2) Morality

Getting to know about people’s code of ethics gives an incredible insight into how they’ve lived/how they claim they’ve lived thus far. The most fascinating aspect of discussing morals is how closely aligned two people’s ethical codes can be, yet their past behaviors bear zero resemblance to each other.

Do you think your morals have held you back in the past from getting what you want? Where do you draw the line between ethics and staying true to your emotions? Has your own moral code ever undermined an impulse you wish you’d acted upon?

3.3) The Future

For this topic, try to steer clear of asking vague and trivial questions such as "Where do you see yourself in five years?" When answering queries like this-people will often apply the circumstances of their present life and formulate their response using circular feedback. Their answer will be something like “I want to be promoted to ______ and I’ll have moved into______ neighborhood.”

Answers like these, are ones you want to AVOID. The goal is to uncover their desires which supersede any of their current means. You want to explore the discrepancy between who they are now and who they desire to be. You want to figure out how they can construct their lives in a way that serves their ambitions.

Some effective alternative questions are:
-If all the chips fell your way, where will you be living and what will you be doing?
-How important is meeting a life partner?
-Do you want to one day own a house and/or raise children? Why?
-Does the endless amount of possibilities actually frighten you from putting your head down and making a choice?
-Is traveling the world an actual pursuit you have or do you just constantly seduce yourself with the thought of it?

3.4) Honest friendship feedback

This one can vary in intensity depending on the length and strength of the friendship. Ideally this is a completely open forum about the progression of your friendship and the benefits/drawbacks to having them in your life. This topic is generally skipped if you've just recently met this person.

HOWEVER, if you feel some romantic chemistry, an effective maneuver would be addressing this topic lightheartedly, which would induce some valuable level 3 flirtation. For instance--

You: I’m really glad you came into my life when you did Brittany.

Her: Haha you mean like, two hours ago?

You: Yes. My life was incomplete at 9:30. It’s midnight now and not only am I woke, but…

Her: But what? Spit it out!

You: I'd like to wake up woke, next to you.

Her: OMG same.

Alright back to having this conversation with longtime friends. Some questions to consider: Was there a time when you hurt them but they were too prideful to reveal their wounds? If you could change one thing about them as a friend, what would it be? Where does spending time with them REALLY fall on your priority list?

Remember, the goal of this conversation is not to inspire change. The goal is to clean out any past resentment so the relationship can move forward openly and honestly.

Level 4

You can feel the warmth of the sand between your toes. You and your friend are calmly sitting, listening to the rhythm of the oceans waves. Each crash invokes a thought in your head, but you’re careful on how to phrase it, for the silences have grown bigger. Not from lack of urge, but from deeper rooted thoughts. As the night goes on, the heaviness of each word multiplies, like body shots in the final round of a championship fight. You compose and re-compose the statement in your head before blurting it out loud. Silence is common during level 4 because you're steadily on the cusp of eureka. Level 4 is where you have thoughts you didn’t know you were capable of, until forming them impromptu.

4.1) Legacy

Thinking about a time when we’re no longer around is a demanding concept to fathom, but a truth we must consider. Each of us only make a brief appearance on this planet, and many never escape the hands we were dealt at birth. There’s an innate desire to leave our mark on mankind as a way of validating the amount of time we’ve spent here. Once our fifteen minutes are up, what seeds will we have planted?

You must take into account the following: Was I responsible for more pain or pleasure during my time? Who will remember me? How would I like to be remembered? What will I be remembered for? In what context will people remember me?

4.2) Souls

Have you ever looked at yourself in the mirror for an uncomfortably long amount of time? What’ll happen is you stop judging your physical appearance and you’ll get a tingling sensation down your back. If you can get past the initial hebegebees, this can be a transformative exercise.

You’ll begin to think what really separates me from others? Under this skin I’m just a skeleton with a brain rattling around like everyone else. What’s really in there? What’s that voice in my head that guides my every action? I have a heart and a brain the same size as everyone else, so is it just my physical traits that make me feel different? You’ll wonder what it’s like to wonder what it’s like to be yourself because you’ve never had that luxury. We can empathize, but it’s impossible to figuratively walk in someone else’s shoes.

Is there such a thing as a human soul? Is it a real entity, or just a construction of our mind to convince ourselves of a higher existence? This topic easily shifts into conversations about potential past lives along with experiences of déjà vu and recurring dreams.

Level 5

Congratulations! You’ve made it to the final level of deep conversation. Neither of you have spoken in twenty minutes. You fear that words will sully the moment.

At this point you and your friend are laying in the sand looking up at the stars. Admiring them for their beauty, appreciating them for giving you scope and scale of the universe, pitying them for never being able to gaze at themselves, but also envying them because as far as we know, stars aren’t capable of existential crises.

Level 5 is the ultimate feeling of relinquishment. Your thoughts aren't clouded by time, anxiety or doom. Your mind has such clarity that you stop being afraid of what you'll find. There’s a natural inclination to gaze at the night sky in level 5 and it’s not some common coincidence. It dates back to our ancestors whom would look to the sky for guidance and navigation. We’re doing the same thing but in a different way. We're seeking out internal guidance so we can navigate our deepest seeded fears.

5.1) The Be All End All Question

One of the most memorable quotes in the 2003 Alejandro Innaritu film 21grams is “Whoever looks for the truth deserves punishment for finding it.” This quote encapsulates how it feels to navigate the ultimate question: what is the meaning of life?

This is a paradoxical dilemma because the worst possible outcome for a conversation like this is actually being right. Our answer to this question shapes how we conduct ourselves. If the meaning to life is x then we’ll do y. If there is no meaning, then we won't worry about zigging instead of zagging because everything ends up in the graveyard anyway.

Discussing the meaning of life is a roundabout way of re-stating the driving force behind everything we do. What lights our fire every day? Why do we continue to struggle day in and day out knowing that a century from now, we'll be nothing more than a pile of dust? In this case, it seems that the act of looking for clues, means we’ve already solved the mystery.

5.2) After The Finish Line

Death is the great equalizer of the mankind. It’s the one common destination we all share, but is it the end of our consciousness? Do we graduate to a black hole of nothingness or do we simply revert back to a state of untapped consciousness? (Think how it was before birth)

Are we on Earth part time and does death allow us to exist elsewhere full time? Are our dreams a look into this eventual realm? If our time on Earth is the Oscars, I’d like to know where we’ll be going for the after party. How about the after-after party?

Here’s a recap of all the levels and the topics so you can calculate your score.

Level 1

Relationship endeavors/shortcomings/regrets
Family Issues/feuds/personal vendettas
Hypothetical Harry

Level 2

Religion
Insecurities
Embarrassing personal stories

Level 3

Consciousness
Morality
The Future
Honest Friendship Feedback

Level 4

Legacy
Souls

Level 5

The Be All End All Question
After The Finish Line

To calculate your depth average, add up all the topics that you felt you adequately addressed and divide it by the total amount of topics.

Ex: Insecurities (2) + Religion (2) +Morality (3) + Meaning Of Life (5) = 12

12/4= Your deep conversation was about a level 3 depth. Happy Measuring!