Whatever Happened to the Art of Flirting?

A couple of years ago, single guys were running around like crazy, turning pineapples upside down in their shopping carts in hopes of hooking up with single women pushing carts with equally inverted pineapples. It was supposed to be an urban legend circulating in Europe and the United States, but I saw it with my own eyes. The fad was short-lived. It’s frightening how quickly things die out in the postmodern world. The story now seems like something out of a 1990s paranormal tabloid. Dating rituals have evolved considerably over time. They mutate faster these days, but there have always been plenty of subtle codes for flirting.

In the decade before the upside-down pineapple craze, a popular dating technology allowed single guys to reject single women, and vice versa, by dragging them around by the nose at high speed. The inventors decided that going through life grabbing strangers by the nose was a bit too aggressive, so they created Tinder and similar apps. This allowed the act of pinching someone’s nose and flinging them into a black hole to be performed digitally, a method that is less painful and significantly reduces the odds of ending up in jail or losing your teeth. (RELATED: The Collapse of Courtship for Gen Z)

As it turned out, Tinder became overrun with lies, weirdos, train wrecks, and lunatics of every stripe, driving many people away. After the pineapple fad, the Sunday papers, which still believe they invent social trends in 2026, insisted that people were now hooking up through sports. Sports? It used to be the other way around: you hooked up first and exercised later. But then again, what would my generation know about it? We never made it past the gym reception desk, and we certainly never fueled up on protein gels. (RELATED: The Pal-Partner: The New Low-Key Flirting Trend)

Further back in the annals of the decades, the digitization of dating had already begun. In the 2000s, there were specialized matchmaking messaging services, forums, and even obscure chat rooms for would-be Casanovas, where loners, ugly people, eccentrics, and the clueless all mingled.

[T]he disappearance of gallant men must have happened in tandem with the gradual extinction of those ladies.

In the 90s, by contrast, picking someone up online was a rarity, and friends and family would advise against it, suggesting, rightly, that a blind date arranged over the internet would likely end with you getting shot in an empty lot or dismembered and neatly filed away in some psychopath’s fridge. In much of the West, however, national security is in such great shape today that the same thing can happen to you without even trying to pick someone up. The turn of the century also saw the advent of SMS flirting. Its advantage was that character limits forced bards and poets to be more concise in their declarations of love, significantly reducing the number of sappy clichés that could fit into a single sentence. Today, “ILY” (I love you) is just an abbreviation, but back in the 90s, it was a matter of household economics. (RELATED: BREAKING! Gen Z Haz Sad Because 2 Poor 2 Date)

In the 70s and 80s, pubs were the place to meet people, though that practice never quite died out in the decades that followed. True, younger people don’t frequent them as much, but trends are cyclical. The one thing that never swings back and forth is guys’ desire to approach girls. They always end up deploying their best wit to make it happen somehow, whether in person, online, or on a school trip across Europe.

In the 60s, or so I’m told, love was as fashionable as peace and marijuana, so you could try to pick someone up at any time, from morning till night, and in any setting, from a coffee shop to a wake. In the 50s, the new thing was the house party. For some, the wild abandon of that one big night has lasted to this day: they still haven’t found a girlfriend, and they still haven’t found their way back home.

In the 40s, the name of the game was flirting in plain sight, within the bounds of propriety, of course, so the best places to do it were town squares and promenades. Back then, people also did a lot of flirting at church, though not with the priest. In the 30s, before the war, men and women often made their moves at local street festivals. You might discreetly brush a girl’s hand while, I don’t know, the Bob Dylan of the era was singing, but you could also lose your balls with a single shot. The girl’s father was often lurking high up in a cork oak tree with binoculars and a Winchester 97, tracking your every move as if you were a safari elephant.

In the Roaring Twenties, we still believed in love. Young men and women would size up the crowd at ballroom dances, bobbing their little feet up and down. The promenade itself was a courtship ritual, much like the great crested grebe’s mating dance when he wants to get lucky with a female grebe. Would-be sweethearts exchanged letters, perhaps not overly passionate but written with the courtesy of the Roman Curia. Years later, if the relationship led to marriage, those letters helped ensure its longevity, since disrespect wasn’t even an option.

And, generally speaking, back in the 20s, guys competed not by grooming their eyebrows or wearing their pants so low that their underwear showed, but by being more gallant than the next guy, especially with the girl they fancied. Gentlemen offered a lady their arm while walking, always opened doors for her, and helped her into her coat.

Sometimes I wonder when we lost all that richness of the 20s. I only wonder until I hear the lyrics of the reggaeton and trap songs that captivate young women today and shape their romantic lives. Then I think, well, I don’t know which came first, the chicken or the egg, but the disappearance of gallant men must have happened in tandem with the gradual extinction of those ladies.

Now everyone will call me, on top of being a journalist, which is quite an insult in itself, an old fogey. And they’ll be right.

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