The winking face emoji is mocking us all

This icon of condescension, beloved by boomers, is the symbol of a generationally divided internet
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In 2006, England played their World Cup quarter final against Portugal, a match that Sven-Goran Eriksson’s team ended up losing on penalties. Back in the second half of full time, Cristiano Ronaldo helped get Wayne Rooney sent off, by pleading to the referee after the English striker scuffled with another Portuguese player. Mission accomplished, Ronaldo strolled away – then winked towards the side of the pitch. Whether it was a mocking one, at Rooney’s departing back, or a conspiratorial one, at the Portuguese bench, is lost to history. Either way, it tipped more or less the entirety of the English nation into a cartoon rage.

I sometimes feel a faint stirring of that rage when I encounter the winking face emoji. Like winking itself, it comes loaded with different meanings: it can be flirtatious; it can be jokey; or it can be ironic, delivered to undermine or contradict the text or speech it comes with. Because winking (and its emoji) are so ambiguous, people often get into trouble with them. A wink delivered as playful might be received as perverted. In the 2008 US vice-presidential debate, Republican nominee Sarah Palin’s frequent winking baffled audiences. No one quite knew what she meant. Some took it as a sign of creeping insanity.

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In 2008, hardly anyone had heard of emojis. Now we can’t get enough of them. Well, some people can’t. If you’re young enough to have grown up on the internet, emojis can seem a bit passé. You might let loose a volley of them ironically; otherwise, they’re an occasional garnish. But those who got online slightly later in life love emojis. Have you ever got a birthday message from your aunt or grandma that wasn’t peppered with love hearts? Have you ever received a meme from your dad that didn’t come with a close personal protection team of crying laughing emojis?

And one of the emojis that Gen Xs and boomers seem to love above all is the winking face. There are few messages my parents do not seek to enliven with the winking emoji. Others of a certain age seem no different online. On election day earlier this month, politician-turned-podcaster Rory Stewart posted a photo of a polling station with the caption: “On my way to get my ID 😉”.

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The more I see the emoji, the grumpier I get – the more that cartoon face morphs into a youthful Ronaldo. Because although the point of a wink is often to share a joke, I’m starting to feel that the winking emoji isn’t laughing with me – it’s laughing at me. Maybe it’s just generational angst talking, but the winking emoji has become an icon of condescension from those who have had life pretty easy. Just look at it: it’s not delivering a cool, knowing wink with an otherwise straight face, but a mocking one, attached to a creeping, smirking smile. I can easily imaging seeing the words “if you stopped eating so much avocado toast you could afford a house” followed by the winking emoji. In fact, I’m pretty sure I have.

The internet used to be a weird thing that young people used. Now, everyone of every age uses it, but each generation has a slightly different language for it; their own slang and their own meme formats. For boomers, this means winking face emojis, and pictures of a Spitfire captioned: “The clocks go back this weekend. I’m setting mine to 1940!”

When these different languages crash into each other, hilarity – or rage – can ensue. I know boomers aren’t necessarily rinsing me for my empty property portfolio with the winking emoji, but I can’t help feel like they are. But maybe the last word should go to the Old Testament’s Book of Proverbs, which seems to have anticipated this issue by thousands of years. “Whoever winks the eye causes trouble,” it reads, “and a babbling fool will come to ruin.” Take that, Ronaldo.