A Game

In one of his many insightful talks on the nature of consciousness, self and ego, fear and insecurity, Alan Watts plays a game which he would humorously refer to as ‘chasing the heebie-jeebies’. The point of this game was to reveal the ‘below surface’ thoughts operating when we think.

Take, for example, death. I am afraid of death. It gives me the ‘heebie-jeebies’. Well, what is the problem, death, or the heebie-jeebies? It appears the heebie-jeebies are actually the problem. They make me feel anxious. So being anxious is the problem. Well, I only feel anxious because I don’t think I have been living a full and rich life. So that is the problem. When I think about the absence of richness and fulfillment in my life I run away facing it. So running away is the problem. But, I only run away because I do not know how to answer it. So being unable to answer this existential question is the problem. With each question being another step, as we walk down the stairs we uncover questions we would not originally have asked ourselves.

To take another example: talking to strangers. I am afraid of talking to strangers. It makes me nervous. So, being unable to talk to strangers isn’t the problem, nervousness is. But I am only nervous because I think they will judge me. Okay, so fear of judgement is the problem. I fear judgement because I care so much about what others think instead of what I think. So, my lack of faith in myself is the problem. I lack faith in myself because I focus on my failures rather than my success. Now this is the problem. But I think this way because my failures were always rebuked and my successes were never praised, so I developed a slavish tendency towards self-abuse. So, self-abuse is the problem. Yet, that happened in the past and this is the present, so holding onto my pain is the problem. However, I only hold onto my pain because I cannot think any other way. I cannot think any other way because this way of thinking is known, comfortable, and reassuring. It is all these things because I am afraid. I am afraid of trying something new because I will have to leave my old self behind. If I leave it behind, I become vulnerable and exposed. If I allow myself to do this, I might get hurt. I do not want to get hurt because I am fragile and do not want my security shaken and assaulted. So, perhaps this, then, is the problem.

Of course, you can keep going and going…

The game is insightful, especially when written down, because you begin to see the complex interactions and multi-textured pattern of every thought. While we think in specifics and particulars, behind and beneath (or rather, within and throughout) each thought is a textured and multi-layered process occurring. In the example the fear of death, the fear cannot be severed from feelings (anxiety, dread, disappointment), thoughts (reflections on an unfulfilling present, nostalgia for a lost past, and the expectation of a frustrated future), and bodily sensations (tensing, clenching, restlessness). Everything occurs together in a wonderfully complex process.

The game is a type of hide-and-seek, or rather, a game of chase with yourself, where you try to locate the fountainhead of a particular thought or feeling. Frustratingly, it is like chasing a shadow, no matter how close you get, it keeps getting away. The lesson in all of this is to pay attention, attention to how thoughts are never isolated but imbued with the messages of so many other thoughts in an ever unfolding pattern of complexity.

On Feeling Ugly

You’ve made a point of avoiding it. You consciously avert your gaze. Walking past it one morning, your attention slips, and you come face to face with your reflection in the mirror. The crooked smile, the crippled finger, the attenuated eyebrows. You’ve put on weight, you don’t look happy, your smile doesn’t have the exuberance of photoshopped models on Instagram. Looking at yourself, you can think only one thought: ‘I am ugly’.

Philosopher with Mirror, Jusepe de Ribera, 1600/1652

But there is more to ugliness than meets the eye. We know there are fit people with symmetrical faces, perfect smiles, and voluptuous bodies who think they should live under bridges and demand gold coins from travelers as they pass by; they are trolls after all. And yet, there are people with flat faces, distorted features, and misshaped bodies who consider themselves as Aphrodite’s offspring; the most beautiful creatures to have blessed the face of the Earth.

Believing you’re ugly has less to do with the state of your flesh and more to do with the state of your soul. The difference between feeling beautiful and feeling ugly has, quite surprisingly, very little to do with how we look. Rather, it has almost everything to do with the degree of love and respect we have for ourselves.

In more ancient times, people believed the state of one’s soul was reflected in the state of their body. A leper, therefore, was to be condemned because their physical decay was seen as reflecting the corruption of their soul. A physical deformity was seen as a manifestation of spiritual deformity. Parodying this ancient maxim, our perceived physical ugliness is really a reflection of self-hatred in our soul.

When we say we are ugly, we are telling ourselves that we do not consider ourselves worthy of the love, respect, and compassion we so readily grant to other people. You are not ugly; you are just suffering from a bruised and battered soul. You don’t need plastic surgery, new clothes, or a new haircut. What you need is to feel properly loved and valued, and for someone (else, or yourself) to remind you that you are beautiful, on the outside but more importantly, on the inside, where it counts.

The Brutal Functionalism of the Modern World

The modern world is, in many ways (and with little energy required to find examples), quite ugly. It is not that someone has attempted to make something beautiful but through lack of imagination or lack of will, mutilated the task. Rather, we live in a world that is seemingly unconcerned with beauty altogether.

On the left: the homogenous, grey steel structure commanding every street in Melbourne. It has been designed in such a way that the absolute minimum amount of material has been utilised in order to achieve the goal. One vertical pole, two horizontal joiners for lights, and two diagonal beams for support. It is brutal in its dedication to function and utter disinterest in anything else. This structure is not here to play games, it has a job to do. It is a very serious light. The structure on the right could come from another world, and in a sense, it does. Far more iron has been used than would be necessary to hold up the light. But that is, in a sense, the point, the flourishing waves and curls revel in the excess that is its mark of beauty. It is the very fact that the cascading form of swirls is utterly useless and unnecessary that makes it beautiful. Someone did something entirely unnecessary for our benefit. It is beautiful because it is not just a light; it is a delightful play of contrast between stiff iron yet fragile watery patterns, designed not merely to work, but to be enjoyed.

It is not just street lights that the brutal functionalism of our world reveals itself. Our food is much the same. Think of fast food. The worker might as well be a machine considering how they are treated as mere functions. Mustard, ketchup, onion, pickle, patty. Repeat. There is no love in the fast food experience.[1] It is food as fuel. Food reduced to the lowest common denominator. It is food as input, soon to be expunged as output. One does not savour the flavour or lounge (thus the ‘fast’ in fast-food). Fast food restaurants are devoid of all the things that make eating a humbling and joyful experience because it is not about food; it is about brutal functionalism in the pursuit of efficiency and productivity.

This is not just the case with lights or fast food. One can, with minimal effort, come up with myriad examples. We buy our plants in black plastic pots, devoid of substance and imagination, rather than terracotta or clay. We go to IKEA to buy chipboard furniture rather than visit craftspeople or antique stores.

Perhaps the reason we are all so interested in clothing fashion is because it is one of the few spaces remaining that has not been taken over by zealous devotion to functionalism. The day it is we will all be walking around in grey one-piece suits.

Skyscrapers and housing estates, tables and chairs, dinner plates and cutlery, phones and books; they are all mass produced items like street lights and McDonald’s hamburgers that are devoid of any love, care, and devotion. They are not made with an interest in making something beautiful for its own sake. So, we must ask ourselves, what is it that they are created according to? To what standard? According to what values?

The objects we see are produced according to the standards of efficiency and productivity. These second rate reasons serve a higher value: profit. It is simply more profitable to produce black plastic pots than to invest in terracotta with all the useless (yet wonderful) flourishes. Yet, in the process, something incredibly important is lost: beauty.

Unfortunately, we are not simply buyers and sellers living in a marketplace. We are people, people who wish to live in a world that is inspiring and moving. Art should not be reserved for museums or galleries, art should be a part of daily life, where society itself is a canvas for the flourishing of human creativity.

The notion that we should not or even worse, cannot make our society more beautiful because it would cost too much money is like saying you cannot build the desk you want because it would take too many centimetres. By living according to how much something does or does not cost, we have created a world where efficiency and productivity are the benchmarks for success, instead of how something inspires us, or makes us stop and wonder.

We may have saved ourselves a lot of money in building our street lights the way we did, but we lost something else in the process, something that we will never be able to compute on a profit & loss spread-sheet: we lost an opportunity to make society a work of art.


[1] Like with sex, sometimes we don’t want love, we just want pleasure. It may feel good, but it certainly isn’t beautiful, and there is only so long that pleasure can substitute for beauty.

The Fertility of Silence

Silence is more than a phenomenon marked by the absence of sound. Silence is an ideal. It manifests in at least two forms. The first is what we may call ‘imposed silence’. Imposed silence stems from an inability to speak up. It is the disempowered silence of the listener who is denied access to a voice.

The second is ‘composed silence’. Composed silence is an active process of keeping the busy room of the mind clean. The room of the mind is furnished with things of the past, but composed silence creates a clean slate. As Krishnamurti notes, ‘only an empty cup can be filled’. Composed silence empties the mind so that it may be filled with something extraordinary, fresh, and new.

In the first instance, silence is a negation of possibility. In the second instance, silence is the negative space of possibility. The absence of sound provides the room for the discovery of truth. By virtue of being empty space between speech, silence establishes space for inquiry to occur.

But silence is not an isolated concept. Silence is relational. We cannot make sense of self without other; day without night; foreground without background. So too, we cannot make sense of silence without noise.

But contrasting does not imply opposing. Bad experiences are not opposite to good ones, but are, in fact, the very types of experiences necessary to make sense of good ones at all. Similarly, silence is not opposed to noise, but is rather, the essential ingredient for noise to exist. Silence is the ripening of noise. To take it at its most physical, a sound wave operates whereby the spaces in between are what allow you to make sense of sounds.

If all a man did was talk, he would soon run out of things to say because he has given himself no time to think. Silence is not the absence of thought, but the stage of percolating and ripening. In his moving piece on the fertility of silence, Kahlil Girban writes,

You talk when you cease to be at peace with your thoughts;
And when you can no longer dwell in the solitude of your heart you live in your lips, and sound is a diversion and a pastime.
And in much of your talking, thinking is half murdered.
For thought is a bird of space, that in a cage of words may indeed unfold its wings but cannot fly.

In Gibran’s conception, silence is not a state of being mute or dumb but is an active process where we nurture and expand our own potential. It is the silence of a ripening consciousness, brimming with potential only because it was allowed the space to grow.

Our lives are incessantly busy. We have the demands of home, friends, work, and family. We also have a device glued to our body constantly notifying, prodding, poking, and demanding our attention. But in cultivating silence and its twin sister solitude, we can unplug and get in touch with ourselves as we are, and we might find something we did not know was there.

It’s Not About You

We generally think about narcissism in terms of the neurotic tendency towards vanity, selfishness, unbridled self-love, and admiration. To the extent that this is true, it is only partly true.

We can think about this character profile as the positive (as “+” sign) side of narcissism, where someone identifies as all that is truly good and noble in the world. But there is also the negative (as “-” sign) side of narcissism, where someone finds in themselves all that is unquestionably horrid and despicable in the world. One adds qualities to themselves they do not possess, the other takes away qualities that they do.

Two men are vying for a promotion at a prestigious law firm. Both are highly qualified, productive, well-liked and loyal, both having been there for over ten years (and having started at the same time). At the end of the week when the promotions are announced, as expected, only one of them is the recipient. The successful man walks around the office hi-fiving and loudly proclaiming it was a “no-brainer” to hire someone as brilliant and talented as him. His jocular mood takes a pompous and acidic turn as he turns to the other man tells him he lost out because he was less talented, intelligent, and aspirational. This man, in turn, becomes dejected. He spends the night alone at the office drinking heavily, reminding himself every time he passes a mirror that he truly is the pathetic man he was said to be, and he would have gotten the job if he was more capable, clever, and ambitious.

While we are ready to harbor ill-will towards the first man, we are more reserved in our judgment of the second. However, they are both victims of a similar mentality. Neither man, it seems, creates distance between events and themselves. Both define who they are, absolutely, upon what happens to them. Each man’s identity is so porous, that there is effectively no barrier between what happens to them and how they define themselves. Were the tables turned, it is likely each man would have acted in the same way as the other.

Both men forget, in their own way, that we are not the things that happen to us. To the extent that we allow events to define us, we become second hand people. This is narcissism; being a reflection of what happens around you.

In addition to the dejected lawyer who missed out on the promotion, we could include the unfortunate soul who really thinks ‘it’s not you, it’s me’, blaming themselves entirely for a break up; the man who despite his best attempts, receives a cold shoulder from the beautiful woman at the bar and returns home truly believing he is an ugly troll whom nobody could ever love; and the self-flagellating victim of an unfortunate life who only blames themselves for why things have not turned out so well.

In our self-proclaimed meritocratic society, we are told that anybody can be anything and there are no barriers to self-realisation. While it is an excellent belief-system for the winners, the losers suffer not only loss, but the shame that comes with loss being entirely their fault. We live in a world where success and failure are pinned entirely on the individual. We find it difficult to speak about forces outside ourselves that may influence how things turn out because before a conversation even begins, we act as if they are not there.

The ancients understood how little agency we have. The Romans had Fortuna, the Greeks had Tyche, the Etruscans had Norita, and the early Semites had Gad. These gods served an incredibly important function: they reminded people that life is largely outside of our control and we are often the victims of uncontrollable and unforeseeable forces.

Our secular age has no use for deities. Yet, we should take on the spirit exemplified by the gods of fortune and chance. The next time we blame ourselves entirely for something that has happened, we should start an inner monologue and tell ourselves ‘it is not about you’.

‘It is not about you’ is a reminder that we are not the centre of the universe. We are minor actors on a stage whose edges we cannot even see. While sometimes we may feel like everything is our fault (for better or worse), it is absolutely necessary (for our own wellbeing) to remind ourselves that we are like sailors on an ocean and while we can control the sail, we cannot control the wind.

We should try to catch ourselves next time we feel like saying we are the cause of this misery, the creator of that pain, or architect of the agony; and instead recognise that while we may have played a part, to a large extent, there was only so much we could have done.

Reminding yourself that ‘it is not about you’ is not about being deprecatory, but about being humble; it involves recognising how little control over things you have and in turn, opening up a space where you can see that no matter how bad things might get (a painful breakup, a missed promotion), it is not entirely your fault.

Kairosclerosis

Kairosclerosis is the moment when you realise you are experiencing joy, but consciously try to hold on to it, prompting you to identify with it, break it down trying to understand it, and pick it apart until the delicate experience becomes the dust of an afterthought. Essentially, you can’t just be happy, you need to figure out why, but in the process of thinking about it, you kill it.

Those of us who are Kairosclerotic are victims of our own imaginations. It is not that we do not want to be happy, it is that such a feeling feels so alien, so absurdly out of place, that we have to analyse it, to find out what is going on in the hope that we can develop a formula, a procedure, a method, to conjure this feeling once more.

The Kairosclerotic feels joy and sadness like the rest of us, but they feel (perhaps because their minds are more attuned to interpreting things negatively) that life is essentially miserable, so therefore, when they do experience joy, there arises a feeling of indecency and guilt. They believe (perhaps not entirely incorrectly) that life is essentially suffering and they therefore feel indecent or wrong to enjoy happiness when it arrives. It is essentially a melancholic attitude.

The joy a Kairosclerotic individual feels is soon overwhelmed by another thought; one of all the times they did not feel joy. They cannot help but contrast this brief slither of light against the enormous yawning void of misery and pain that had come before and that will surely come after. They cannot en-joy because their mind immediately sets this moment of happiness against all the moments that came before, emptying the present moment of any liberating and pleasurable potential.

We all know a Kairosclerotic person in our midst, perhaps we are one ourselves. A symptom of melancholy, we do not allow ourselves to be happy because we do not allow ourselves to feel. And if we feel, the greater danger is in feeling something we have not before and in realising that this brief moment of happiness is actually that: brief. We do not want to be happy for just the moment, we want more than a momentary spark in a dark chasm; we want to smile and live a life where when we are happy, we don’t need to question what the hell is going on.

FOMO: Fear of Missing Out

There is no shortage of people, books, movies, and advertisements around to remind us that we live exceedingly boring and unfulfilling lives. The model you follow on Instagram taking snapshots of them lounging on a balcony in Ibiza, the author extolling you to travel to every major European city to become more interesting, the Mercedes ad reminding you that the new A-Class model will give you a riding experience unlike anything you have ever felt in your 1992 Subaru. The modern world excels in reminding us at every turn of just how much we are missing out on.

Naturally, we begin developing, at first a suspicion then later a conclusion that our lives are intolerably bland, monotonous, and dull. Soon our dissatisfaction mutates into fear, fear that we will live and die unfulfilled, that we have only experienced at most, a second or third rate life.

Our fear of missing out arises because we have tacitly accepted a way of looking at the world that we may never have said aloud: the good life is one that it is the quantity of experiences that makes life worth living, not their quality. The more we have and the more we do, the happier we will be, or so the thinking goes.

It would benefit us to remember that we simply cannot have it all. For every choice we make, we disclose the possibility of making others. Life is, essentially, always a trade-off of possibilities. If you wear the blue tie, you simply cannot wear the green one (although, you will be better off not wearing a green tie anyway). Ties are one thing, but this holds true elsewhere. In entering a monogamous relationship, you disclose the possibility of being with other people. This is not necessarily oppressive; it is up to each of us to decide whether what we choose is worth all the things we can no longer choose as a result. But the cheater is one who suffers from a crippling sense of FOMO. They are unable to be satisfied with their choice because all they see are choices they can longer make.

Contentment is found by focusing on what we do have, rather than on what we don’t. Happiness is not reserved exclusively for the rich and famous. It is a blessing that can be as graciously bestowed as you enjoy a cup of tea with your grandma as it can enjoying a party with celebrities. We would benefit by reminding ourselves that obscure books can be more beautifully written than New York Bestsellers, that a quiet walk along a local lake can be just as enchanting as the cobblestone streets of Paris, and that talking to a child may be infinitely more interesting than talking to a model with millions of followers.

We will find contentment when we stop comparing one experience with another. Anything in life, from staring at the Mona Lisa in the Louvre to staring a tree in your backyard can be immensely gratifying if we take the time to appreciate it. The point is, it is not things which make life worth living, it is our attitude that does.

With patience and a mind no longer comparing one thing with another, we will find the flutter of a butterfly through our bedroom window the most mesmerising of experiences we could have, and will therefore, not feel like we are missing out on anything.

The Sincerity of Nature

In our society, nothing is quite as it seems. This is not nihilistic philosophy or conspiratorial thinking, but rather simple acceptance of the fact that there is so much pretence everywhere we look. The fake smiles of service industry employees, the public relations of large corporations promising us that they really care, the businesspeople hurrying around the city in suits pretending to be strict and proper but who really want to do nothing more than eat Doritos and watch Seinfeld. The previous model phone now with curved edges and sold as a new phone, the same trickle-down economic theory promoted as cutting-edge economics, the same exploitation of workers but with a friendlier corporate smile. Added to this we have plastic plants as plants without plants, Astroturf as grass without grass, non-alcoholic beer as beer without beer, and steroids as muscles without muscle.

In a world of ever increasing proliferations of fakery and pretence, from the manufactured perfection of social media profiles and scripted ‘reality’ TV, to manipulative advertising and political sophistry; nature becomes a sanctuary of truth in an increasingly fake world.

With a properly attentive eye and open mind, there is much to learn from the humble tree. It does not pretend to be something it is not. It does not tell you that it doesn’t need the sun to nourish it, or the soil to hold it; that it does not enjoy the whistle of birds or the cool embrace of the wind. It simply is, in all its magnificent glory, without a single drop of pretence or superficiality. And in this, there is a wonder strikingly lacking from our society: the splendour and confidence that comes from simply being without pretending to appear as something else.

In part, this explains the joy in watching children play. They might not be doing anything we would consider particularly interesting. They may just be drawing a happy face in the sand, stepping on an especially crunchy leaf, or admiring a bird on a branch. But what makes these activities of children so enamouring is the complete lack of self-awareness and pretence with which they do it. Like a bee tickling pollen out between petals, or a tree reaching for new splinters of light, the child simply is, without needing to pretend to be one thing or another.

In a meditation penned in 1876 on the honesty of trees, the poet Walt Whitman wrote,

How strong, vital, enduring! How dumbly eloquent! What suggestions of imperturbability and being, as against the human trait of mere seeming. Then the qualities, almost emotional, palpably artistic, heroic, of a tree; so innocent and harmless, yet so savage. It is, yet says nothing.

green and brown tree during daytime photo – Free Image on Unsplash

In a language beyond words, the natural world speaks with honesty unmatched in our incessantly superficial and mediagenic society. The contrast between being and seeming which Whitman observes in trees is precisely what Hannah Arendt would capture a century later in her work The Life of the Mind, in eternal conflict between being and appearing.

Through social media we continually gravitate to a way of life where visibility becomes the pre-condition for existence. We no longer exist unless others see us. In this world, we exist only through the eyes of others, through our Facebook and Instagram profiles, becoming the ‘second-hand’ people Krishnamurti lamented. We change how we speak, how we walk, how we dress and in turn, how we think, in order to appease the imagined standards of people around us, people who also, unfortunately, are doing precisely the same.

Among the many lessons of nature, from the essential interrelationship of everything, the importance of harmony, and the necessity of tenderness and compassion; one of the most important lessons, and one we are in most dire need of learning, is how to be authentic and honest versions of ourselves. When we stop obsessing over how others may perceive or judge us, and focus on being instead of fretting about how we are appearing; we take the courageous leap into a new way of living, one that is at once more honest and graciously authentic.

You Deserve To Be Happy

Like Stockholm syndrome of the ego, we can grow to depend on and even cherish parts of ourselves which are crippling, harmful, and even self-destructive. Subservient for so long, we forget we can live differently. It isn’t that we don’t want to be happy, a part of us certainly does, but a more powerful part of us cannot let go of what is making us unhappy. In a way, it is not a lack of will power, but rather a lack of imagination that keeps us tied to what harms us.

For those of us who are chronically depressed, anxious, angry, or avoidant, it is not that we fail to see happiness as something worthwhile, or that we do not think leaving our depressed or anxious minds behind is a worthy goal. Rather, we are unable to because (with always different reasons why) so much of our agency and self-identity is tied up with being depressed, anxious, angry or avoidant that we feel we cannot lose them without losing ourselves in the process.

After so long, being unhappy comes to be seen as natural, normal, as ‘the way things are’. Deviating from this state would be scary. We cannot imagine a life outside of the cage. It is reminiscent of slaves given the opportunity of freedom, would not run away. Never knowing a life outside of slavery, they failed to see their slavery as such and therefore, saw no reason to escape. When we become enslaved to our depression, anxiety, or fears for so long, we begin to forget there was once a life without them.

Making matters worse, both slave and slaver are within us. We are punished and also see ourselves as worthy of punishment. In such states, it becomes appropriate and entirely reasonable to tell ourselves that we do not deserve to be happy. Someone as pathetic and wrong as us should not be allowed to traverse the lofty summits of joy. We must remain in the murky depths of despair where we belong.

For all the pain, misery, and conflict that come from defining ourselves in such a way, when we define ourselves as unhappy or anxious, or depressed or avoidant human beings, we are doing something very powerful. We are making statements about who we are as people. What we then tell ourselves is that despite how lowly and miserable we might be, at least we are something! It might be a depressed or anxious or avoidant person, but being something terrible is at least better than being nothing.

For those of us who are chronically depressed, anxious, angry or avoidant (or any other type of miserable condition we are afflicted with), the call to be happy can be utterly frightening. While we can intellectually understand that happiness is worthwhile, it doesn’t feel that way. It feels unsettling, even terrifying. It is something we have never done before and we have a tendency to prefer a problem that we know to a solution that is unknown. What will happen to us if we allow ourselves to be happy? We will no longer wall ourselves up, enclose ourselves, and put barriers between ourselves and others. The bars of our cell are seen as protecting us from danger rather than what they are: bars keeping us trapped within ourselves.

It takes incredible courage to unlock the cell (because you have had the keys all along), walk beyond the bars and allow yourself to be happy. It is easy to be depressed or anxious or avoidant, especially if this is all you have ever known. The courageous first step out of the cell can be daunting and especially frightening and it helps to have a dear friend you can trust, or even a psychologist, to walk with you and to remind you when you forget or try to crawl back into the familiar cage of self-punishment that you indeed, truly deserve to be happy.

On First Dates & Asking the Right Questions

While a first date may be considered successful if your partner considers you witty, charming, intelligent, and despite your earnest protests to the contrary, good looking; the most important indicator of a successful first date is connection.

It is unfortunately the case that much of our lives are – to perhaps too great an extent – quite superficial and that we rarely connect as humans with open hearts and open minds. We talk, but do not communicate. It is not for nothing that communicate shares an etymological root with commune.

While we may not reveal much of who we are to people we know well, it is especially so when we begin dating. We keep much of ourselves hidden (for fear of rebuke) and pretend to be calm and composed even when troubles in the home or heart leave us feeling confused and in need of a good hug.

Seeing as the first date is somewhat an audition for the emotional capacities of the soul on the other side of the table, first dates are an opportunity to ignore a tendency towards obfuscation and be honest in a way that we rarely are about who we are.

With this in mind, it becomes clear that questions about what someone does, what they like, or what is their favourite film or book, are focusing energy in the wrong direction. While they may be stepping stones in conversation, they say next to nothing about who someone really is; their passions, desires, regrets, dreams and fears.

We often play on the surface of life, but truly getting to know someone requires depth. The first date requires us to start thinking and speaking differently. We need to learn the art of the date.

We want someone who will know (and respect) us for who we are deep down, but that is only possible if we ask the right questions. Questions such as,

When was the last time you cried, and why?

We focus incessantly on the positive aspects of one’s life. But everyone experiences pain, grief and sorrow; they just often keep it to themselves because it doesn’t get so many likes on an Instagram post. Asking such a question shows that you aren’t so tawdry and banal, and are interested in the part of your date that they don’t often show to the world.

If you lived your life a second time, what would be one thing you would have done differently?

In asking this, you show a concern not just for what is the case, but for what could have been. It shows an interest not in success, but in failure, regret, and disappointment. In drawing out the conflict between who someone is and who they wished they could have been, you will learn more than you ever could have asking about their book collection or Spotify playlist.

What frightens you?

Everyone appears (at least on the first date) infinitely more composed and self-possessed than we are. This question is an invitation to draw out the weakness that lies buried within all of us and to reflect together on how we may share the same fears and insecurities.

Do you want more from your life? What is it?

We all yearn for something more than what we have. We are, by nature, creatures of thirst, striving to reach new goals, ideals, standards, and new versions of ourselves. In asking this, you demonstrate an interest in what makes your date’s life meaningful. Nobody is fully content, and in finding out what someone considers as lacking, you get a good indication of what is important to them.

These questions seem depressing. But, in another way, they are attempts to dive deeper into another’s soul. It is a misjudgement to think that a question about crying will put someone off just because it is about tears rather than rainbows. Perhaps that will put some people off, but would you want to date someone so superficial? It is significantly more rewarding to be emotional yet insightful, than mildly amusing yet dull.

At the end of your encounter, your date may turn to you and inform you that they have never been asked so many insightful questions about who they are as a person before. What you have demonstrated is that you are interested, not in the surface play of life, but in whom they are as a unique, complex, human being with wants, wishes, desires, and regrets.

The unfolding origami of the soul becomes more enchanting with each layer that is peeled away, revealing the complex interconnecting forms which make us who we are. There is nothing more seductive than someone who is keenly interested in getting to know who we really are as a person. It is something infinitely more seductive than money, power, fame, or looks.

The beauty of these questions is in the act of self-revelation and in finding that your date at the other side of the table is still there, listening attentively and sharing their own stories, accepting you for the humble, awkward, damaged person you are, appreciating how you extend the same generosity to them.

Some other questions:

  • What qualities in your friends do you admire most?
  • When you think about your childhood, what do you feel was missing?
  • What are you addicted to?
  • What are you worried about at the moment?
  • Do you think the people around you know you for who you really are?
  • Do you ever feel like an impostor?
  • What do you want to change about yourself?
  • What part of yourself do you never want to lose?
  • When you think about what makes a good life, what comes to mind?