How To Date In Our Modern World

The importance of knowing exactly what you’re prepared to settle for

First a disclaimer: although I’ve dated off-and-on over the last twenty years, most of what I know about modern dating has been acquired by means of conversations with friends and listening to accounts tearfully delivered during actual dates.

This means that my dataset is limited, is likely subject to selection bias, and is entirely anecdotal.

Which makes it perfect for a Medium article.

And so, without further ado (and some further adon’ts) let us embark upon our mutual exploration of dating in the first quarter of the twenty-first century.

We begin with men, for males outnumber females on all dating sites and apps by a ratio of around 7:3. This is actually an excellent thing because it makes us desirably desperate. Few women can resist the charms of a man who’s not actually been in the presence of a flesh-and-blood female for at least twelve years and who therefore shakes uncontrollably throughout the date.

Men know that two things reliably drive women wild.

First, obviously, is the dick-pic. Presenting one’s potential-future-beloved with a picture of one’s fleshy pride and joy early in the relationship is the perfect ice-breaker. Nothing says I want to get to know you as a fellow sensitive human being better than a dick-pic.

The second is lying. What woman wouldn’t fall hopelessly in love with a man whose profile says he’s 1.86 meters tall, has a full head of hair, owns three homes, drives a Maserati, and in his picture looks like someone who could make a living modeling for top-rank magazines? Especially when, in person, he’s really 1.68 meters tall, sports a tasteful comb-over, lives with his mother, and took an Uber to the restaurant? Oh, and it goes without saying (but we’ll say it nevertheless in case someone’s fallen asleep in the back of the room) that he must have changed a lot since that picture was taken.

Given these never-fail ploys it’s not surprising that the typical single male has more second dates than he knows what to do with and is getting fantastic sex every single night of the week. Because, c’mon, he deserves it. Especially as a mature man of forty-six (really 57, but let’s not get bogged down in petty details) he’s focusing entirely on equally mature women of twenty-one.

Turning now to women we can see that the gender formerly known as the fairer sex likewise knows how best to arrange matters so that they may lead smoothly to a life-affirming long-term relationship.

As nearly every woman states clearly in her own profile that she has no time for liars, she understandably knocks a decade or so off her actual age. Because that’s not technically lying; it’s more of a micro-adjustment. Likewise her photo (which is actually of her) was taken recently within the last half-century.

When it comes to the sensitive matter of weight (a topic upon which no man should dare to tread) it’s obviously necessary to report the truth, which is that scales can’t be trusted, every day is different, and the new diet she’ll commence next week will anyway close the gap between what she puts in her profile and her current weight, a mere 115 kilos.

Arriving at the rendezvous just a little late in order to signal she’s a busy woman and not at all desperate she’s determined to make it abundantly clear that sexual intimacy is off the menu for at least two more dates. Everyone knows no one respects a woman who’s willing to Give Her All before the requisite rituals have been performed, namely (i) the lengthy exposition regarding her past relationships and why all men suck, (ii) the consumption of too much alcohol, after which various quasi-risqué remarks will mislead her date into thinking that perhaps she might one day actually be prepared to condone some physical intimacy, and (iii) the evening’s denouement in which many tears will be shed post-dessert in a flood of self-pity.

Meanwhile the man is equally anxious. After all, you only get one chance to make an utterly misleading impression. He’s come armed with a few sure-fire topics to get the conversational ball rolling. First there’s his hilarious anecdote about the time he accidentally went straight from the fourth tee to the sixth and then mis-read the water trap so he had to spend fifty-seven minutes trying to play his ball from underneath half a meter of the wet stuff before finally sinking that little round sucker at just 507 over par.

Then there’s the tale of his ex-wife and how she took the house, two of the three cars, most of his 401(k), and slept with his best friend. And his best friend’s best friend. And all that guy’s cousins. And the woman behind the counter at the local drug store. But hey, that’s all water over your shoes and who’s counting?

To round off the evening he’s confident his funny story about how he discovered he’d contracted gonorrhea at a colleague’s stag night will be just what’s needed to put her completely at her ease and get her totally in the mood for sex. Which is why he’s there in the first place.

Of course, this is merely one of several ways in which matters may unfold.

Let us turn now to the phenomenon of The List Of Requirements.

Many of today’s women don’t want to take chances. Just like security personnel at US airports, they are convinced that if one makes one’s requirements plain then compliance is assured. Just as all terrorists absolutely always tick the YES box in response to the question Are you or have you ever been a member of a proscribed terrorist organization, so too all men will always respond truthfully and accurately when presented with The List.

By stating very clearly in her profile that she hates liars and cheaters and timewasters and fakes, she is saving herself from unfortunate revelations down the road. This flawless strategy demonstrates both her intellectual perspicacity and enables her to focus her energies only on men who truly deserve her attention.

Furthermore, what red-blooded male wouldn’t be excited by the prospect of meeting a woman who, right from the outset, makes her needs so clearly understood? Especially when all her photos feature such irresistible adornments such as cartoon ears, a pink bunny nose, and colorful butterflies circling her head?

Perhaps that’s why sensitive and thoughtful men also make use of The List, as per “No fatties, no high mileage, no giraffes, no one over the age of twenty-two” and ensure that in every picture their eyes are safely ensconced behind impenetrable sunglasses. Because, “let me gaze into your mirror lenses” is perhaps the most romantic phrase one person can ever utter unto another.

Once two people actually meet, they may engage in light-hearted banter as per the following exchange:

Her: “So, what do you do?”

Him: “I’m a software engineer at FaceGooeyFruit.”

Her: “How much do you make? Do you have stock options? How much are they worth?”

Him: “Well, I bought both my homes outright with cash. But mostly I spend my money on videogames. You ever played SmashBurnKill? It’s super fun. They even have a female character, so it’s totally non-sexist.”

Her: “I like to travel. Do you like to travel?”
Him: “Sure. I went to Tahoe one time. Lots of mountains. But I like VR more.”

Her: “VR? Is that in Honduras?”

Him: “Uh, so what do you like to do?”

Her: “Oh, you know, the usual.”

Him: “Cool. Me too!”

Her: “I only date winners. It’s my special rule.”

Him: “Wow! Great rule.”

Her: “I find it saves time.”

Him: “So, like, what do you do with all the time you save?”
Her: “I spend it weeding out losers.”

Him: “Makes sense.”

Her: “I don’t think this is going anywhere.”

Him: “Oh. OK. So… wanna fuck?”

Her: “Yeah, I guess so. I mean, now that we’re here and all….”

Today, at any point in time, well over one hundred million people worldwide are using dating websites and smartphone apps to search for The One. Faced with a seemingly endless supply of Not The One Under Any Circumstances, people become both more desperate and more cynical.

And this is a shame. Because people are basically people, which means we all need human interaction and we are all imperfect.

The hi-tech dating game makes it seem like there’s always someone out there who’d be absolutely perfect for us if only they’d answer our message or swipe right on our profile too.

But the truth is that dating sites, like all marketplaces, are highly asymmetric.

Just as everyone wants to get in on the newest boom stock and no one wants the hundreds of penny stocks that sit forever at the bottom of the market index unloved and unnoticed, so too everyone wants the half-dozen super-hot men and women who get 95% of the action on whatever site or app they happen to appear while the vast majority (who all want to get a date with one of these super-hots) languishes, unable to rise to the same unrealistic expectations that they have of everyone else.

So we often end up becoming bitter and we blame the world for the fact that we don’t get our wishes fulfilled. Why can’t I have what I want? This cry is as strident at sixty-four as it was at sixteen months of age. Why doesn’t the universe revolve around me? If everything happens for a reason that was meant to be, why aren’t I with some drop-dead hottie right now and forever after until (my) death do us part?

As I wrote at the opening of this piece, my own dating experiences have been limited and perhaps that’s spared me from undue disappointment. I’ve tended to give myself a break after a fairly short time rather than persist like some manic hamster on a wheel that spins but never goes anywhere. When I’ve gone on dates, I’ve treated them simply as an evening out, an opportunity to meet someone I’d otherwise never encounter. A chance to listen and learn a little about someone else’s life and experiences.

Perhaps, if things go well, there may be the potential for some sort of friendship. Otherwise we will part after an amicable couple of hours, each having experienced something of the other and thus done what humans do, which is to be social. And that’s sufficient in itself.

Undue expectations can crush potential. Frantically searching for The One is paradoxically going to make it far less likely we’ll ever encounter our own personal unicorn. But by being relaxed, by having few expectations, and by looking at a date as simply a chance for two people to have a conversation for a couple of hours, we open ourselves up to something positive.

And surely that can’t be bad?

Anyone who enjoys my articles here on Medium may be interested in my books Why Democracy Failed and The Praying Ape, both available from Amazon.

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