Dating Archives - The School Of Life

For most of human history, relationships were relatively simple for a banal yet immovable reason: it was extremely hard to meet anyone acceptable – and everyone knew it. There were only a few people in the village, travel was expensive and social occasions few and far between. 

This had many drawbacks: it encouraged people to accept offers from suitors they were unconvinced by, it meant that characters who would have delighted each other died lonely and unfulfilled because there were a few mountains or a river between them.

Our technologists have used their genius to correct these historic obstacles and provide us with unending choice. Meeting someone new is now a constant possibility. But this breakthrough at the level of introduction has obscured an ongoing challenge at the level of ultimate purpose: we may have become easier to meet, but we are not any easier to love.

Photo by Kev Costello on Unsplash

We remain — each one of us — highly challenging propositions for anyone to take on. All of us are riddled with psychological quirks that serve to render an ongoing relationship extremely problematic: we are impatient, prone to making unjust accusations, rife with self-pity, and unused to expressing our needs in a way they can be understood by others — just to start the list…

That we can meet so many people has beautifully obscured our ugly sides, breeding in us the charming yet misleading idea — which engulfs us any time we hit difficulties — that we are in trouble because we have not until now met ‘the right person.’ The reason why there is friction and longing has, we tell ourselves, nothing to do with certain stubborn infelicities in our own natures or paradoxes in the human condition as a whole, it is only a matter of needing to hunt further for a more reasonable candidate who will, at last, see things our way.

The promise of choice has drained us of the patience and modesty necessary to grapple with the tensions that are prone to come our way whomever we might be with. We forget that almost everyone is a charming prospect so long as we know nothing about them. Part of what it takes to be ready for love is to imagine the difficulties that we cannot, as yet, know too much about in detail; the bad moods that will lurk behind the energetic smiles, the difficult pasts that lie beneath the lustrous eyes, the tangled psyches that reside beneath a stated love of camping and the outdoors.

Even though there are hundreds of other people we might meet, there are not — in truth — so many people we could really love. Dating apps may have made it infinitely easier to connect but they haven’t helped us in any way to be more patient, imaginative, forgiving or empathetic, that is, any more adept at the arts that make any one relationship viable. Most of the issues we experience with a given candidate will therefore show up, in comparable guises, with almost anyone we might stumble upon.

The real work we should be doing isn’t — once we have had a reasonable look around — to keep trying to meet new people; it’s to get to the root of what makes it hard to live with any one person we could alight upon.

We will be ready for love when we surrender some of our excited sense of possibility and recognise that though we might have many choices, we don’t — in reality — have so many options. It may sound dark, but this will, in its own way, be a liberating realisation that can help us redirect our energies away from the exhausting circuit of new encounters towards a search for the kind of mutual emotional maturity on which true love can one day be built.

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A powerful instinct when we meet someone we’re attracted to is to try to please them – and we naturally assume that the best way we might do this is to indicate repeatedly how aligned we are with their views and choices on all matters great and small.

On an early date, when they happen to mention that they love dancing, we will therefore signal that of course we love clubs as well. Or when they explain how boring they find museums, we will hide that on a trip to Berlin last year, we spent a whole fascinating day in the galleries of the Altes Museum. 

We may not state direct falsehoods but we will stretch and bend the truth to its limits so as to create an impression of near-total alignment. Our will-to-please can reach a peak around sex: we naturally can’t risk introducing them to the actual byways of our erotic imagination. We just claim to want – by miracle – exactly what they want.

Along the way, it rarely occurs to us that they might be performing some of the same rigmarole for us, that they might also be adjusting their self-presentation in subtle but powerful ways to fit in with what they take to be our preferences and values. There’s a tragi-comic aspect to our deepening mutual attraction. Two decent people are trying to be as nice as they can. No one is setting out to deceive and yet, gradually, a set of hugely misleading and dangerous ideas about who each person really is, are getting established. 

Our overwhelming will-to-please can inspire us to move in together and later to marry. And then – inevitably – the prolonged, intimate scrutiny that coupledom brings will reveal the scale of our mistaken expectations. In a sequence of disillusioning stages, we will each be saddened, disappointed and shocked to discover who we have ended up with. There will be recriminations, rows and fragile reconciliations until, in the end one or other party comes to the grim, but still surprising conclusion that we were never compatible. 

Or we may stick at it with growing misery. We will face a life-time of holidays that never involve the museum visits we crave. We will have to resign ourselves to never having had the kind of sex we want. Or, even more grievously, we will eventually embark on a furtive life; we will seek out the moments when they’re away to pursue needs we’ve pretended not to have. Until one day our double-life is exposed – and we will drown in bitterness, fury and sorrow.

Yet the origin of such nightmares was only ever a hugely touching, but painfully flawed and risky, devotion to being an easy match. We wanted to be simple; and yet we have ended up with a very complicated mess. 

A genuinely simpler approach is to be somewhat complex from the start. When dancing comes up, the sensible lover should immediately describe their loathing of the activity; when the museum theme is raised, they should frankly evoke their passion. When it comes to their routines and tastes, they should dare to mention their pleasure in a very well-wiped kitchen work-top or explain what it means to them to be awake in the early hours, when the world is still sleeping and their mind is at its most adventurous. 

There is no need to be brazen or demanding. And there is no requirement that our date agree or even stick around beyond dessert (or the main course). Some will run away and should. 

In order to disclose our truths, we need a basic sense of acceptability, we must know that we are not perfect but that we are not for that matter wholly abject or shameful. Our attitude to the kitchen might be a little excessive without being delusional. Our very early rising might be unconventional, but it’s perfectly sane – all things considered. Around sex, we know that a preference might be statistically unusual without lapsing into evil. Our inner conviction that our oddities are essentially reasonable allows us to present ourselves to another person without fear or defensiveness. 

Our candour then arms us with the right to ask the other to reveal – with similar honesty – what may be individual and difficult about their own characters. If they insist that they are really very simple and ‘easy’, we are allowed to be gently but firmly sceptical. They are a human being, and to be human is to be complicated. It cannot possibly be true that they exist without significant quirks. The problem with any potential partner is rarely that they are too weird, but that they haven’t come to terms with their distinctiveness or found a language in which to introduce others to who they are in a way that may be plausibly understood and accepted.

Being straightforward on dates is in the end a mechanism for two people to fast-forward time – and to spare themselves agony in the process. We should know that a polished surface isn’t a true picture of who anyone can be. Only once our mutual complexities have been outlined can we sense, with enormous relief, that we are in the presence of a fellow mature and pleasingly direct individual. We will have the simpler relationships we desire, when we can dare to reveal and accommodate the actual complexities of human nature.

In the 1930s, the Swiss psychologist Hermann Rorschach was seeking to understand more about the contents in the unconscious minds of his patients – when he hit upon the notion of asking them to respond to the legendary inkblot test that still bears his name. Rorschach found that ink randomly poured onto pieces of paper that are then folded ends up leaving an array of distinctive shapes behind. These shapes don’t actually represent anything, they are inherently ambiguous, but they are suggestive of a number of things in the outside world: one shape might look a bit like a bird, another might resemble a fish or a cloud. The interpretations they can give rise to are almost infinite – which was precisely the point in Rorschach’s eyes.

By being shown an ambiguous image and asked to say what came to mind, Rorschach believed that we would naturally reveal some of our latent guiding fears, hopes, prejudices and assumptions. The test would be a guide to how patients really felt about themselves and the world. Any Rorschach inkblot image will have no one true meaning, but different people will see different things in it according to what their past and underlying mentality predisposes them to imagine. 

So, to one individual with a warm childhood and a rather kindly and forgiving conscience, the image below could be seen as a sweet mask, with eyes, floppy ears, a covering for the mouth and wide flaps extending from the cheeks. Another, more traumatised by a domineering father, might see it as a powerful figure viewed from below, with splayed feet, thick legs, heavy shoulders and the head bent forward as if poised for attack.

The image isn’t in itself of anything, but what we end up saying that it ‘is’ or that it ‘means’ is really a story about us – not an account of what is going on in the real world.

Many situations we encounter in life have something important in common with Rorschach inkblot tests: we don’t quite know what they mean. They are ambiguous. The facts are unknown – and could point in a whole host of directions. For example: someone is late, but we don’t know why. Or someone has asked to see us, but we don’t yet have a reason. Of these ambiguous situations, none is more painful, more intensely scrutinised or more telling of the state of our own self-worth, than what we can call the missing phone call.

Let’s imagine we met someone at a party a few days back. They seemed friendly. They smiled a bit. We couldn’t tell for sure if there was a spark of interest in them – or indeed quite how much there might have been in us. But there was a little something there for sure. On parting, we exchanged numbers and they promised to give us a call.  But that was a few days ago now, and still there has been nothing.

We are deep in an ambiguous situation where we don’t know what something means – and in this sense, we are right back to Rorschach’s inkblot test. Because we can’t solidly interpret the meaning of the silence, what then starts to count is what is in our unconscious. If our unconscious mind is benign, if we broadly like ourselves and trust the world, then the missing phone call can be interpreted benevolently: probably they’re busy, maybe they had a partner and thought twice of it, maybe they’ll get around to it next month, perhaps they lost our number… 

But if on the other hand our self-esteem is low, and our past predisposes us to feel unworthy and unlovable, then the interpretation will be quite different: now the ambiguous ‘inkblot’ comes to represent something altogether more sinister. It’s proof of what we are always on the verge of suspecting; that we are unworthy, that no one can ever love us, that we are disgusting and it’s only a matter of time till everyone finds out, that it’s a joke to even imagine that anyone could delight in us: that we are – in essence – unloveable.

What we need to cling on to fervently at such moments is the moral of the Rorschach test: that we just don’t know – and that what we’re saying we can ‘see’ is actually a projection from the past, not an assessment of reality. We don’t, and never will know the facts. All we have is pure ambiguity and what we’re doing in the absence of information is projecting ideas that say far more about us than they do about the motives or circumstances of the person who hasn’t called (and which we’ll never know). 

We need to be kind to ourselves; the missing phone call isn’t yet another proof of our wretched, unloveable condition. It isn’t one more harbinger of unkindness and sadism. It is – through adult objective kindly eyes – one thing above all else: a missing phone call for reasons we’ll never know and should never presume we can know. The catastrophe we fear will happen, that no one will love us, has already happened, long ago. We don’t need to keep seeing monsters in every inkblot and every missing appointment.

In the course of any adult life, there will be periods when we’ll end up involved in that slightly odd, slightly unrepresentative and invariably slightly challenging activity: looking. Most people around us won’t be any the wiser, but with greater or lesser subtlety, we will be scanning: suggesting coffees and lunches, accepting every invitation, giving out our email addresses and thinking with unusual care about where to sit on train journeys. Sometimes the rigmarole will be joyful; at times, a bore. But for a portion of us, as many as one in four, it will count as one of the hardest things we ever have to do. Fun won’t remotely come into it. This will be closer to trauma. And it will be so for a reason that can feel more humiliating still: because, a long time ago now, we had a very bad childhood – one whose impact and legacy we still haven’t yet wholly mastered. 

It may not look like it, but babies are also looking out for love. They’re not going out in party smocks or slipping strangers’ their phone numbers. They are lying more or less immobile in cribs and are capable of little besides the occasional devastating cute smile. But they too are looking out for someone’s arms to feel safe in; for someone who can soothe them, someone who can stroke their head, tell them it will all be OK when things feel desperate and lend them a breast to suck on. They are looking – as the psychologists call it – to get attached.

But unfortunately, for one in four of us, the process goes spectacularly wrong. There is no one on hand to care properly. The crying goes unheeded, the hunger unassuaged. No one smiles reliably or cuddles confidently. There is no welcoming breast. In the eyes of the care-giver, there is depression or anger where there should have been delight and reassurance. And as a result, a fear of existence takes hold for the long term – and dating becomes a very hard business indeed. 

For those of us who experienced early let downs, there is simply little in us that can ever believe that a search for love will go well – and we will therefore bring an unholy commitment to bear on ensuring that it doesn’t. The dating game becomes the royal occasion when we can confirm our deepest suspicion: that we are unworthy of love. 

We may, for example, fixate on a candidate who is – to more attuned eyes – obviously not interested; their coldness and indifference, their married-status or incompatible background or age, far from putting us off, will be precisely what feels familiar, necessary and sexually thrilling. This is what is meant to happen when we love: it should hurt atrociously and go nowhere. 

Or, in the presence of a potentially kind-hearted and available candidate, we may become so demanding and uncontained, so unreasonable and urgent in our requests, that no sane soul would remain in contention. We will spoil any potentially good impression by bringing a lifetime of self-doubt and loneliness onto the shoulders of an innocent stranger.

Alternatively, unable to tolerate the appalling anxiety of not yet quite knowing where we stand, we may decide to settle the matter by ourselves, preferring to crash the plane than see how it might land. We’ll interpret every ambiguous moment negatively, for sadness is so much easier to bear than hope: the slightly late reply must mean that they have found somebody else. Their busy-ness must be a disguise for sudden hatred. The missing x at the end of their message is conclusive evidence that they have seen through our sham facade. To master the terror of another letdown, we go cold, we respond sarcastically to sincere compliments and insist with aggression that they don’t really care for us at all, thereby ensuring that they eventually won’t.

To escape these debilitating cycles, we need to accept that we’re searching for someone to love us while wrestling with the most fateful of background suspicions: that we don’t in any way deserve love. 

It’s only by properly mastering what once happened to us, the letdown we first experienced as infants, that we can start to separate out past trauma from present reality – and therefore learn to navigate the ambiguities and occasional risks of adult dating. It isn’t that we have been told that we don’t deserve to exist; they’re just busy tonight. They don’t loathe us, they’re married to someone else, as lots of people (who we carefully have chosen not to look at) happen not to be. They’re not peculiar, it’s just unfair and overwhelming to ask someone you’ve known for twelve hours to make up for a lifetime of loneliness.

We need to see that this is not the first time we have been ‘dating’. We have done it before long ago and it was the ways in which it went very wrong that holds the key to our adult errors – our intensity, our coldness and our lack of judgement. The catastrophe we fear will happen has already happened. The challenges we set up for ourselves are attempts to get back in touch with a trauma we haven’t either understood or mourned.

We can in time learn to ask people on a date because we grasp that we’re not thereby asking them what we think we’re asking: do I deserve to exist? We’re asking something far more innocent, and far more survivable were the answer to be negative: might you be free on Friday? And we can survive because, even though we once got terribly hurt in the nursery, we are now that most resilient of things: an adult. So we have many other options, we won’t (as we once feared) die of loneliness if it doesn’t work. We can take our time, we can allow things to emerge, we can tolerate ambiguity. And with such security in mind, we can begin to do that most momentous of things: without risking our sanity, see if someone we like might – after all -want to go out tonight.


It’s generally easiest to love human nature from afar – to be touched by the kindness, intelligence, beauty and grace of our fellow creatures when we are, perhaps, surveying them from 30,000 feet or across a few centuries of history. The true challenge is to hold on to a little of this benevolent regard when they are across the table and the first course has only just arrived.

We know, in theory, that many of us are disturbed, that emotional trauma is widespread, that up to 60% of us may have severely disrupted attachment styles, but the reality remains surprising. Much of the difficulty is shielded from us in those far easier kinds of intercourse, friendship and work. People can do a good imitation of sanity until it comes to love. Through dating, we are offered a front row seat on the spectacle of psychological disturbance.

We may be tempted to rush over the details of the extremely peculiar date. We resort far too easily to the word ‘psycho’. We would do well to reflect on – and perhaps in a melancholy journal – keep a note of the Varieties of Madness Commonly Met with On Dates. The pathologies include:


One realises, gradually, that every question has gone in one direction only. No feather of curiosity has drifted back one’s way. At first, there was a certain natural vivacity that kept things afloat. Now one wonders what kind of neglect they must once have endured to feel that a few moments of interest in another person could be so dangerous. While waiting for a taxi, they briefly touch our arm and make us promise that next time, we really must tell them a bit more about what’s going on in our lives.


There’s nothing wrong with the lighter topics. It can be fascinating to hear about someone else’s plans for their apartment, their trip to the coast, a cousin who recently visited from abroad or how light the traffic has been of late, all things considered. The problem stems from the strength of the underlying determination not to be known. They have come, but only on the condition that their true self (apparently the repository of some powerfully threatening memories of unacceptability, loss or pain) won’t have to attend.


We may be drawn, initially, to their downbeat reticent manner. They may make a few darkly comedic remarks about themselves and life more broadly. But the negativity starts to weigh; there are never happy endings, everything is awful, nothing (including this evening) can work out. They are something far less palatable than melancholy: they have sheathed themselves in a cloak of cynicism to mask an impregnable terror of hope.


They appear very keen from the first. Their manner is overtly attentive and seductive. We can’t help but be flattered until we realise that none of it has anything to do with us. They just labour under a need to ensure that any and every candidate will end up desiring them – at which point, without calling back, they will feel more bearable to themselves. The idea of being wanted is so strange to them, they are addicted to hearing it from more and more people – though they can never believe it and will punish anyone who thinks more highly of them than they think of themselves. A lot of people will fail to receive texts, will have subsequent meetings cancelled and will wonder what they might have done wrong, because three decades ago, a grown up was severely disinterested in a very small person asleep in a crib.

If all this were not already so difficult, there is another agony that may await us: that by a miracle of psychological good health, the candidate will – unexpectedly – be entirely wondrous: funny, kind, self-aware, realistic, tolerant and imaginative. Yet, as becomes subtly and very gracefully evident as the meal progresses, they will be wholly indifferent to us too. They will see through our defences, they will spot our madness, we will be the ones described as psychos in the lacerating precis of this encounter they will give to their friends in the taxi home. We hadn’t really realised how lonely we were until this evening – or what a fun but profitless sport it is to try see through people.

We are never as shy and gauche as we are when attempting to seduce someone we deeply like. The thought of someone this perfect coming to take an interest in us seems at once tantalising and entirely implausible. We develop vertigo and, too often, fall.

Behind our insecurity lie two conjoined fears: that we are exceptionally awful. And that the beloved is exceptionally perfect. Both ideas are hugely destructive – and false.


However, the road to greater confidence about our own nature is not to start to tell ourselves that we are, after all, brilliant. It is to examine more carefully how brilliant any other human being can plausibly be – and conclude that we are no more awful than the next soul. We are so closely in contact with our own ridiculous sides, we cannot – from within, if we are halfway honest – have many illusions about ourselves: every day, we are made aware of our inherent clumsiness, error and absurdity. By contrast, we only ever see the carefully constructed facades of everyone else, which is what can make them seem – quite unfairly – more  impressive than they in fact are.

We shouldn’t try to reassure ourselves of our own dignity; we should grow at peace with the inevitable nature of our but also everybody else’s ridiculousness. We are idiots now, we have been idiots in the past, and we will be idiots again in the future – and that is entirely normal. There aren’t any other available options for a human being.

Once we learn to see ourselves as already, and by nature, foolish, it really doesn’t matter so much if we do one more thing that might look quite stupid. The person we try to kiss could indeed think us ridiculous. But if they did so, it wouldn’t be news to us; they would only be confirming what we had already gracefully accepted in our hearts long ago: that we, like them – and every other person on the earth – are something of a nitwit. The risk of trying and failing would have its sting substantially removed. The fear of humiliation would no longer stalk us in the shadows.

Furthermore, it is properly unhelpful ever to think of someone we want to seduce as particularly special. It is normal, of course, to be momentarily dazzled by beauty or intelligence, but we should quickly recover our poise and remember that our beloved is, after all, only  human. In other words, that behind the alluring facade, once we know them better, they will have a litany of irritating habits, insecurities, obsessions and flaws. To give us further confidence, if we did kiss and even one day marry this person, we’d almost certainly be quite unhappy a lot of the time. Our intimidated feelings before a prospective lover stem from a melodramatic sense of how much is at stake. This paragon will, with time, prove to be a lot more complicated than they appear and will at points be plain heart-wrenchingly maddening. This dark knowledge should relax us as we struggle to cross the room and speak to them: we are not, in fact, faced with a divine being balancing our fate entirely in their well-formed hands. They are an ordinary creature beset with all the tensions, compromises and blind spots we know from our own selves – who will, if everything goes really well, in substantial ways eventually ruin our lives.

We can approach our date with the down-to-earth confidence of one misery-inducing human reaching out to another to start a relationship that will, in time, at many points, feel like an enormous mistake. We can import into the seduction phase some of the (usefully relaxing) ingratitude that we naturally experience once a relationship has started – and use it to get love going.

We should, before heading out for the evening, tell oneself that one is of course something of a cretin and an imbecile, but then so are they, and everyone else we will meet. One or two more acts of folly should, thereafter, not seem like they matter very much at all.


Our present dating habits can feel like a natural part of existence, but in reality, they’ve only been around for a very short time and, we predict, won’t continue for too much longer in their current form. Dating has a history, which it pays to try to understand as we navigate the ritual’s paradoxical and often confusing priorities.

Let’s take a selective look backwards – as well as a peak forwards – at the history and future of dating:

27 March 1489, Medina del Campo, Spain

In a treatise signed between England and Spain, the two-year-old Tudor prince Arthur is formally engaged to Catherine of Aragon – who is at that point three years old. It’s an extreme example of what is an entirely normal practice all over the world in the pre-modern era: relationships are strategic transactions between families, where the feelings of the couple themselves are of no importance whatsoever. The idea that you might love, let alone be physically attracted to, the person you end up with would be deemed profoundly irresponsible, if not plain peculiar.

July 1761, Amsterdam, Netherlands

The publication of Julie, a novel by the French Romantic philosopher Jean-Jacques Rousseau, which becomes the fastest selling book ever written. The novel tells the story of Julie, a beautiful young woman from an aristocratic family who is expected to marry someone of her standing – but, contrary to all the rules, falls in love with her middle-class teacher, Saint-Preux. However, they cannot get married because of the differences in their social status. Rousseau is on the side of the unhappy couple – and his novel is the first major statement of the idea that relationships should essentially be founded on the feelings that exist between people, and have nothing to do with class, lineage or family concerns. But, as yet, Rousseau and his novel see no way of upturning the social order: you still marry who your parents and society tell you, but now at least, with Rousseau’s help, you can feel very sorry that you have to.

March 1855, Rome, Italy

In the major Italian novel of the 19th century, I Viceré, by Federico di Roberto, two characters, Lucrezia and Benedetto, are in love but can’t marry because Lucrezia’s mother refuses to give her permission on the grounds of social propriety. Crucially, the mother is shown to be old-fashioned and narrow-minded; couples formed by ‘reason’ are, the novelist suggests, a lot less happy than those guided by instinct. The book works with the growing Romantic assumption that relationships should be based on sentiment and that the best chances of finding someone we can get on well with over a lifetime is not to find out what their job is or whether they come from a good family, but whether we experience an overwhelming physical and emotional attraction in their presence. Marriage must be a union consecrated by feeling.

1892, London, England

The most successful comic play of the year – Charley’s Aunt – turns on the fact that Charley has invited Kitty to lunch on a date but, at the last minute, learns that his aunt won’t be able to join them. This creates a panic because a dating couple should have a chaperone, an older woman whose presence will ensure that nothing very intimate can be said or done. Charley’s solution is to get a male friend to put on a dress and impersonate his relative. The comedic atmosphere of the play suggests that the old rules around dating are firmly on their way out and are accepted as having some of the fustiness of a maiden aunt. The audience is meant to agree that dating is for the best when couples are left on their own to discover how they feel; there should even be a kiss at the end if things go swimmingly, as they do for Charley and Kitty.

1914, Eastbourne, England

The young George Orwell gets into trouble at school when he is caught reading Youth’s Encounter by Compton Mackenzie: the first novel published in England that describes unsupervised adolescent dating. We’re starting to move beyond the odd chaste kiss: dating starts to be about sex as well.

June 23, 1960, Washington DC, USA

The US Food and Drug Administration approves the first oral female contraceptive pill. The idea that a date can happily and uncomplicatedly lead to sex becomes not only an emotional but now also a practical possibility.


Los Angeles, 1998

Speed dating is invented and the romantic comedy You’ve Got Mail – the first major film based around online dating – is released. Both encourage the idea that it’s important to search very widely before selecting a possible partner. By now all the elements of modern dating are finally in place: firstly, parents have nothing to do with it; secondly, all considerations of money and social status are deemed ‘un-Romantic’ and unimportant; thirdly, you are meant to be swiftly emotionally drawn to someone in order for a relationship to be deemed legitimate and viable in the long term; fourthly, sex is interpreted as a central part of getting to know someone – and lastly, you’re meant to have a lot of dates (and possibly meet quite a few horrors on the way) before finally and happily settling down with that archetypal figure of the modern dating scene: The One.

Brussels, March 2009

The European Union releases a report that reveals that 50% of married couples in countries across the union end up divorced after fifteen years. Though entirely ignored by Europe’s dating couples, the report quietly raises the question of whether instinct is really any better guide to a good conjugal life than the old parental or societal rules used to be – as well as hinting at how much more miserable we can end up being when the sole justification for relationships is understood to be the intense emotional and sexual happiness of the two participants.

Might there be another way to find our partners going forward? Where might dating be headed in the future?

Singapore, May, 2075

Artificial Intelligence has finally arrived, human nature has at last accurately been understood – and dating as we know it dies. For the first time, machines can entirely accurately predict who should belong with whom. Internet dating algorithms, for so long about as faulty as medieval brain surgery, achieve their promise: machines now swiftly find for us the optimal choice of partner for a lifetime together. They know who is available, what our quirks are, and who out there can best compliment them. All the rigmarole of dating in the Romantic era is done away: we no longer have to wonder whether we have found the ‘right’ person; a machine that we trust as much as we now trust doctors, tells us when we have located our destiny. We no longer have to rely on chance or random encounters. We no longer have to keep asking our friends and hoping to be introduced. We don’t have to listen to our parents, we don’t have to take along a maiden aunt, and nor do we have to listen to those equally unreliable entities, our subjective feelings. Couples are not always deliriously happy, but they at least have the satisfaction of knowing that they are with the person they should, all things being equal, be with.

© Flickr/Ilana



Way back in 1489, there wasn’t any choice for Prince Arthur and Catherine of Aragon; now there is no choice either, but in 2075, it is a psychological machine that has determined the choice.

Occasionally, people get a little nostalgic and curious about the old-fashioned, rather haphazard and sometimes thrilling Romantic way of dating. Some of them might dress up and recreate the ritual, like people who nowadays have fun on weekends trying out what it was like to row in a long-boat or live in a wigwam…

All of which should give us a humbling sense of how particular and complicated contemporary dating truly is. We shouldn’t blame ourselves if, at the end of yet another barren or ambiguous date, we feel in need of a little guidance.

The goal can be stated simply enough: the overwhelming priority, when on a date with someone we like, is to persuade them to like us back.

But the simplicity of the mission masks the complexity required to achieve it. Typically, the advice focuses on externals: what to wear, when to unfurl a napkin, what to order… But such counsel, however well-meaning, is at odds with what we ourselves know about attraction: that it is profoundly focused on psychology.

However much we may deny it to friends, a date is ultimately a search for a potential long term-partner. So what really renders someone attractive on dates are signs that they are emotionally well-equipped for what good-enough long-term relationships require. The capacity to find an ideal full-bodied Chianti on a menu may be impressive, but what we’re really alert for are signs that someone is going to be a decent companion twenty years from now when we have received a difficult medical diagnosis or are feeling weepy and ashamed at the progress of our careers.

Here then are some of the things we might do to prove attractive to another person on a date:

i. Tell them that we are a bit mad

We might, in the course of the conversation, light-heartedly drop in that we’re not quite sane. Perhaps we have great difficulty getting to sleep or get very anxious in social situations. Maybe we are often deeply sad on Sunday evenings or have a painful rivalrous relationship with a sibling.

The key is that, as we reveal these vulnerabilities, we can suggest we have a mature, compassionate, unruffled relationship to them. Yes, we may be a little mad, but we are eminently sane enough to know about and be unfrightened of our follies; we have mapped them, are able to warn others of them and can protect those we love from their worst sides. What we require in a partner is not someone who is perfect, but someone with a good handle on their manifold imperfections – who can warn us of these in good time, and not act them out in ways that will ruin our lives.

© Flickr/Quinn Dombrowski

It is deeply reassuring to witness vulnerability well-worn and madness confidently understood; to see someone mature enough to talk about their immaturities in an undefended and serenely curious way.

Over the long-term, every possible partner will be revealed as rather crazy in some dimension of existence or another. So what really counts is not whether or not they are psychologically complicated, but how they relate to this complexity: the degree of insight, calm, perspective and humour they can bring to bear upon it.

Conversely, there should be nothing more terrifying on a date than a person who sticks a little too aggressively to the idea that they are totally sane and entirely normal. Anyone over the age of twenty possessed of the idea that they are ‘easy to live with’ has evidently not begun to understand themselves or their impact on others. We should probably skip desert and head home early.

ii. Ask our partners how they are a bit mad

The enquiry should sound playful, natural and wholly compassionate. Having laid out our flaws of character, we should take it as a given that – despite their evident strengths and accomplishments – our date too will have a litany of their own madder sides. We should create a safe space in which we imply that it is extremely unsurprising that our date should be a bit ‘broken’ in certain areas; everyone is. We can gently enquire into what makes them in particular anxious or depressed, what was untenably difficult in their childhoods or what they in particular regret and are ashamed of. This can prove charming because what we’re ultimately looking for in love are not people who find us perfect, but people who will not flinch from the sight of our wounds. We want to be seen for who we really are and forgiven; not mistaken for someone else, idealised – and then one day condemned.

© Flickr/Steven Guzzardi

iii. Reveal we’ve been a bit lonely and sad lately

We often assume that people want to hear that things are going brilliantly for us – and that we become winning for others when we can show we’re triumphing in the world. But what really warms us to others is evidence that they share in some of the very difficulties and confusions that we are beset by in our private selves. If love involves a desire for an end to loneliness, then some of what we no longer want to be lonely with are our more melancholy dimensions that most people have no time for or interest in – and that we therefore have to take care to hide from others in a bid to look competent and strong. How seductive, therefore, to stumble on someone around whom we sense we will no longer have to be jolly in a brittle way; someone who can give us room, through their own candour, to confessions of feelings of loss and sorrow. There can be few things more charming on a date than to hear, from someone who looks extremely self-possessed and competent, that they’ve been feeling unusually isolated and very perplexed of late. They’re showing us the fertilised soil in which our love can grow.

iv. Pay some compliments

We can, understandably, get anxious at the idea of having to pay our date some compliments. The approach can feel too direct, demanding, almost sleazy. But there is an art to good compliments that starts from a different place: a recognition that most of us struggle to maintain a basic grasp on what is decent and good about us, and privately hunger to hear from someone else certain basic but psychologically-sustaining things about our characters (that sound unbelievable when we try to say them to ourselves): that we aren’t wholly stupid, that some of the things we say have value; that we are sometimes funny or perceptive and have a few qualities to contribute to the world.

We can be so worried by our own inadequacies that we forget that the person across the table will have an equally large share of them – which it lies within our power to calm. With our date, we run few risks rehearsing one or two of the reasons why we found them a decent person to invite out; we should not underestimate how deeply – in the quiet of their souls – everyone tends to hate themselves.

© Flickr/Dmitry Boyarin

v. Blush

For anyone with a tendency to blush, the idea that there might be something positive about going uncontrollably red in front of another on a date can sound absurd. But however uncomfortable it may be to blush, doing so indicates a range of admirable character traits we should honour in ourselves and welcome in others. Far from a disability, blushing is a sign of virtue. It’s strong evidence that one is, almost certainly, rather a nice person. We tend to blush from a fear that something about us might bother or prove unacceptable to other people. We blush after we’ve told a joke and worry that it might have come across as inappropriate or offensive. We blush when we are concerned that something we said sounded boastful. We blush because we told a little untruth, feel ashamed and fear others immediately see through us. We blush that we may desire someone who might not feel the same way about us – and whom we really don’t want to bother.

In other words, blushing is powered by an unusually strong ethical sense. It is generated by a terror of making others uncomfortable, a horror of inconveniencing people, a distaste for seeming arrogant or entitled and an overwhelming qualm about saying anything untrue.

Excessive self-doubt can, of course, blight our lives. But blushing seems on the edge of something properly worth celebrating: a high degree of self-knowledge and an awareness of how disturbing or annoying we can be to others – an imaginative exercise that will help to keep our unappealing sides properly and fruitfully in check over the long-term future we’re auditioning for.

© Flickr/Mike Burns

vi. Do something clumsy

We knock over a glass on the table; drop some food down our front or jog the bread basket off the edge of the table. It feels like a disaster but so long as we handle our own clumsiness with humour, and admit good-naturedly the scale of our own ineptitude, we can turn the situation to our advantage. We are signalling that we know that what matters isn’t simply the errors we make but how we explain and frame them to those around us. Across a lifetime, we’re going to do plenty of ridiculous things – so what counts is to be able to show at the earliest moment, as we mop up the olive oil or wipe a drop of tiramisu from a nearby oil painting, that we can handle adversities and reversals without fuss or drama; that we are modest and wise enough not to expect perfection from ourselves and will hence be able to forgive slip-ups and failures in others.

These antics and more belong to a properly rich sense of what we might need to talk about on the audition of our lives we call, with touching modesty, a date.

Dating brings us close to a particular strand of philosophy that, the rest of the time, might not seem particularly relevant to our lives: existentialism. One of the movement’s major proponents – Jean-Paul Sartre – developed a set of ideas that help explain, and give dignity to, the anxiety, excitement and at points vertigo we may experience as we go through the dating ritual.

A key concept of Existentialism is expressed in Sartre’s somewhat obscure but useful phrase: “Being precedes essence”. What Sartre meant by ‘being’ are the bits of our life that we are free to choose for ourselves: how we live, what job we do, how we conceive of what happens to us. And by ‘essence’, he refers to things that lie outside our command: our biological nature, the flow of history, the position of the stars…

What Sartre wished to point out to us, in a spirit of wanting to liberate us from certain rigidities of mind, is that ‘being’ should ultimately be thought of as more important than ‘essence’. However much we sometimes like to tell ourselves that things have to be the way they are, there are in fact many radically different possible versions of ourselves available to us; we can choose to an extraordinary extent how things might be for us. But much of the time, Sartre felt, we don’t give this open-ended aspect of our identities enough space in our minds. We assert that the way we live is inevitable and fixed, and imply that we have no agency over our stories. But Sartre argues that this is an illusion: the kind of person we are right now developed as a result of all sorts of small and large decisions: it could have been very different, and may be different again in the future according to the way we exercise of our will upon the raw material of life.  

Surprisingly enough, it is dating that can bring home some of the richness of this dramatic existential insight. It is in our dating years that we feel, perhaps more than at any point before or since, how much our future is undefined, how little is preordained, how many options there really are; how frighteningly free and fluid things can be.

With each date we’re sketching – even if very lightly – a possible future. If our date on Wednesday goes well, we could conceivably be looking at (for instance) a life in which we have relatives in the highlands of Scotland, in which a lot of the people we spend time with are in the technology sector and in which we’ll probably move country several times; we might in time also have a child called Hamish or Flora. Alternatively, if our date on Friday evening goes very well, we could be edging towards a life in which we’ll be spending a lot of time in Amsterdam; we’ll get drawn into the theatre world; if we have a child they might be called Maartje or Rem and they’ll have a former cycling champion as a grandfather and an Indonesian grandmother.

© Flickr/drufisher

Once we make our choice, things may well start to seem as if they always had to be, that there was some essence that we were always moving towards, that we had to end up with little Maartje or sweet Flora crawling on the carpet towards us. But in the dating period, we are closer to a grander and more visceral truth: that there is no single script.

Sartre’s second big point is that properly recognising our freedom can lead us to a state of huge but inevitable and in a way salutary anxiety. Conscious of our real liberty, we take on board that we have to make decisions and yet, at the same time, that we will never have the correct and full information upon which to base them with the sort of perfect wisdom and foresight we might desire. We are steering largely blind, forced to make choices that ideally we’d leave to the Gods but that in a secular world, we have no option but to take on for ourselves.

As we date, we may wonder: who should we settle for? For how long do we keep going? How can we tell whether this one or that one is right?

Sartre’s answer is that we can never properly know but that we are never more properly alive and authentic than when we are turning over such enquiries: the fluidity of our destinies is then palpable, with all the strangeness and wonder this implies.

Too often, the sense of fluidity is lost. We assume that what is had to be and that we have no further choices left open to us. The dating years defy such views.

No wonder if they feel like high stakes. Sartre wished to embolden us for the sort of challenges they present to us. Dating pushes aside the veil of our normal complacency and reveals the sublime, terrifying and, at the same time, thrilling uncertainty of existence. We should, with a host of existential challenges before us, at the very least, not be too bored.

Our initial impulse might be to pick up on a current event, some detail of the environment or a few impressive things about our careers.

But if a date is at heart an audition for the emotional capacities required for the success of a long-term relationship, the real purpose of conversation must be to try to understand the deep self of the other person.

We know we will be doing well if, at a certain point, our date reflects that they’ve never been asked so many psychologically-weighty questions – and are we perhaps some sort of psychotherapist in training…? Such comments playfully reflect how comparatively surface most chat ends up being and how unnerving and yet delightful it can be to sense that for once the focus of another’s interest is firmly on the details of our souls.

This is some of what we might ask in an attempt to take the measure of another’s deeper self:

– What has made you cry in recent times?

We’re not only concerned with what goes well for them; we’re accepting of, and curious about their reversals. We know there are painful sides of life for everyone, we’re not going to insist on levity or deny them the right to grieve. We’ll also be sure to tell them in turn what brings tears to our eyes.

© Flickr/Kurt Bauschardt

What was difficult in your childhood?

Without anyone meaning for this to happen, parents inevitably bruise and damage their children. With a light touch, we’re trying to get a sense of their particular take on the drama of growing up. All of us end up a little distorted by our experiences: over-vigilant or too relaxed; too concerned with money or overly indifferent to material goods; frightened of sex or excessively decadent. They won’t be unique in having been messed up, we’re clear on this score, but their disturbances will be fascinatingly specific to them. We’re signalling that understanding their child self will be vital to grasping how they behave and who they are as adults. It will also lay down a reserve of compassion at moments when their adult selves are overwhelmed by the dynamics of the past.

– What do you regret?

Our lives are crucially defined by the roads that weren’t taken, by the choices we bungled, by the situations we ruminate upon in the early hours. Because there is such a risk of humiliation in revealing where we messed up, if we can be a patient and compassionate listener, we will be doing something for our date that almost no one has ever done for them – at least outside of a professional therapeutic context. We will be gifting them the honour of feeling heard for their mistakes and of being reassured that these are just an inevitable feature of being human; it will be a luxury far greater than being taken to a fancy restaurant or roof-top bar.

© Flickr/Mikael Colville-Andersen

– To whom would you like to go back and apologise?

An associated enquiry, this one focuses on the guilt we accumulate as we stumble through our lives. It’s a question that both leaves room for confession – and offers atonement.

– What would you want someone to forgive you for?

Gently, we’re probing at what they know is tricky in their own characters. We aren’t brutally asking what is wrong with them (they’d take offence). We’re inviting them to admit to one or two ways in which they have noticed that they can cause difficulties for others. We’ll need to have some examples of our own follies to confess to straight after.

© Flickr/Quinn Dombrowski

– What have your exes not understood about you?

Their past relationships are the vital repositories of clues as to the success of their future ones. We’re wondering how well they can pinpoint what went wrong and whether failure has provided them with an occasion to learn rather than merely lament or blame.

– What would you ideally want to tell your mother? And your father?

There might be tears at the thought. There can be so much buried sorrow in the history we share with two people on earth we tend to love and hate in almost equal measure – and owe so much to. We will listen to what parents were too brittle, too defensive or too proud to hear. It’ll be everything that never comes out at family gatherings, but so badly needs to be aired.

– In what ways do you feel like a bit of an impostor at work?

We’re normalising that we all invariably feel like we don’t entirely measure up to what is expected of us professionally. We’re providing a refuge for a sense of incompetence that we take such pains to hide from the world in normal circumstances. We’re inviting the other, at last, to let down their guard.

Having exchanged these questions, and others like them, over many hours, we may feel something odd starting to happen: we may sense ourselves falling a little in love. The process isn’t mysterious. It’s just that we’re getting to know one another’s deeper selves, with all the longings, errors, terrors, regrets, weaknesses and fears involved. There is simply nothing more seductive than this kind of mutual self-revelation, love being in large part the gratitude we register when we feel accepted and seen – as well as the compassion we experience when another person lets down their defences and trusts that we will be kind to them.

Supplementary Early Date Conversation Options

– How did your childhood leave you less than ideally equipped for life?

– Which of your friends do you envy the most?

– What do you worry about in the middle of the night?

– What kind of character trait that you don’t possess do you find attractive in others?

– What do you look for in a very close friend?

– What too often goes wrong in conversation?

– What kind of ideal extra sibling would you have wanted to have?

– Complete the sentence: When I start to like someone, I worry that…

– Complete the sentence: If I was not so shy, I would…

– Complete the sentence: If someone truly knew me, they would…

– In what respects are you still the same person you were as a child?

– What would you like to change about yourself?

– In what ways is your family especially odd?

– What are you prone to be addicted to?

– What do you fear people might say about your behind your back?

– List your top three worries in your life at the moment.

– What has been the role of money in your family?