Relationships • Dating
Two Reasons Why Online Dating Is So Miserable
At first blush, it’s a little confusing why online dating should attract so many cries of protest and rage. Why is this medium the site of so much agony when – on paper – it should simply present us with a broad array of possibilities for love?

The bad reputation isn’t unearned; it is indeed a very painful area. But there are two clear causes for the trouble, and two identifiable remedies.
The first cause is naive or sentimental hope. A section of the online population constantly finds themselves connecting with characters they are immediately extremely enthusiastic about – people they would love to build a relationship with, but whom they then gradually discover are not as interested in them as they should be.
Apparently, these characters are very busy at the office, their phone fell out of the train, they’re off to Italy for ten days, their best friend had an operation on their big toe, they have to travel to another city to buy an extension for their garden hose… They may eventually meet up for a coffee, they may be very smiley during the occasion, but there will then be further, enervating ambiguity as to whether, like an elusive deity, they will ever deign to make another earthly appearance.
All this is admittedly ghastly but, with immense sympathy, let’s offer a sober interpretation: the suitor is, to an important degree, bringing this on themselves. And they are doing so by being excessively sentimental. They are seeing signs – very clear signs – and are opting to ignore them. They are not being honest about what they are up against because they are scared; scared of another negative verdict, scared of isolation, scared of the damage to their self-esteem that every rejection brings, scared of dying alone. These are extremely honourable fears, which deserve all our compassion. What we should never do is avoid them.
At the very first sign of disinterest – the very first moment when the target of our desire doesn’t answer our messages or speaks vaguely of an intention to contact us ‘after their best friend’s cousin’s wedding in Finland…’ – we should, with greater self-protection, sit with ourselves and reckon with the dark truth head-on: they don’t like us very much. They may like us a little bit – enough to meet us for a walk or a museum visit. We’re not repulsive to them. But, crucially, not enough to love us. Not enough for us to bother a moment longer. This isn’t how true love ever begins. These people aren’t shy; they aren’t touchingly inarticulate. They are not properly interested – not to the degree that they need to be for a relationship to have any chance of working. True love knocks down the door to make itself heard, and our door is resolutely untouched. Someone delighted by us smiles all the time, asks us one question after another and messages us at once. They may not have time, but they find it. They are thrilled by us; they can’t wait to see us again. We must therefore cut the waverers out of our hopes with a surgeon’s sanguinity. There isn’t a second to waste. We should let out a cathartic scream, cry very briefly – and then continue on our odyssey. Anything less is an insult to our vulnerability.
Then there is another cause. If one section of the online population is woefully sentimental, another is woefully vain. They cannot admit that many of the people they have casually signalled an interest in aren’t, in fact, remotely characters they’d consider dating if they had better options. Unfortunately, they have only the promise of better options – this is the overriding principle of the online world – but no concrete prospects right now. So they do the obvious, vain and self-serving thing: hang onto their B-list targets without any real intention of responding to their hopes, keeping them close but never too close, just in case; half in and out of the warmth, suspended between life and death, to allay their anxieties about their own futures.
It’s only in the digital age that we can afford to be so irresponsible; to wink pleasantly at so many people we don’t really like; that we can acquire a pool of Category B suitors to cheer us up when the A pool runs momentarily dry. In the old world, the price of any seduction was extremely high. It took a long time to win someone over, it demanded a lot of money, one had to buy flowers and go to many elaborate balls. People would growl if they saw us spread our attentions too thinly. So we concentrated only on the ones that really, really mattered.
Now we flirt while lying in the bath or waiting for the bus. We signal interest in a hundred people without ever raising our heartbeat – nodding at a vast array of passersby without taking the slightest responsibility for the emotional chaos that is unleashed.
There would be peace if both sides (and it may, ironically, be the very same people who are guilty of both behaviours) took on board two awkward facts: firstly, that there aren’t so many people they really, really like – and secondly, that there aren’t so many people who really, really like them back. In the intervening period, while waiting for a proper resolution to the emotional chasm, rather than pretending to like where they don’t like and hoping where there is no hope, both sides should relent: the suitors should accept that they are being toyed with, and the pursued should stop smiling at anyone other than those whom they are profoundly convinced by.
There would – if these two rules were obeyed – be a lot less reason to keep looking at our phones (which is why the industry is so careful to stay silent). The wait for reciprocal affection would be far longer and a great deal more uneventful, but we would be a great deal more likely not to suffer so intensely, to be able to hold on to our dignity, to exercise more, and to read some good books in bed. We would, every day, walk a far less humiliating route to the love we so badly want – and, at this point, so richly deserve.