You may have noticed that actual grown-ups with jobs and mortgages have begun to pepper their texts with emojis. To begin with, it was an occasional smiley face or heart but it has escalated to avocados, martini glasses and dancing girls. You may, at first, have been put off by this, but by now it barely even registers. Is this new flowering of expression, this effusion of wink-faces and balloons, dignified or even OK? It’s hard to say for sure. 

A few years ago in class, in a discussion of George Orwell’s Politics and the English Language, one of my undergrads said that emoji use had changed the way her mind worked. A boss had asked her to do work on a Sunday and she had replied: “On a Sunday?! OK, I’ll do it 😜 .” She realised she could no longer figure out how to convey that she was a little irritated by the request but generally a good citizen and willing to do the work in language alone. She couldn’t figure out how to get the lightness across without the wink face. She had lost the ability or inclination to attempt any nuance of tone with words.

This seemed chilling to me at the time — and still sort of does — but slowly, without my fully realising what was happening, emojis began to creep into my own texts: a sad face, a hat with confetti, a monkey covering his eyes. 

I think most of the over-30s I know have begun to use them too; either joyously or a little abashed. But it’s hard to know if we are doing it in quite the right spirit.

A teenager I know dots her texts with “🐟 👻 ”. They mean nothing, but convey a mood. They are festively embellished “Hi!”s. The over-30s tend to get hung up on the idea of communication, that when you are texting you are actually saying something, that there is some meaning to convey, whereas what the young have generally perfected is the absolutely vacant, contentless connection, endless insipid variations of “I am here!” Bright bits of nothing. Just hanging out. 

One day I was arranging a drinks date with an Israeli artist I know. She is an enthusiastic emoji user, and sent a precise and colourful string of emojis: 🍸🎉 💃 😘. . I thought it was only polite to write back with my own string: 🍷 🍹 💕. My 13-year-old, who had the misfortune of sitting next to me at the time, nearly died, she was so horrified. She started sending me parodies of this exchange, strings of emojis used specifically as in an actual sentence: 🍸🍕 ⛵ 🏊 💖 . She took screenshots of the original conversation to send to her friends so they could also nearly die. 

***

One of my twenty-something students explains to me that she uses generic emojis, such as 😃 , to put someone she doesn’t know well at ease, but uses other emojis “in excess and slightly ironically with friends”. The trick is, of course, the irony. When people over 30 try to use emojis, the irony is not quite there — or quite right — because the trying is so painfully evident. They are so clunkily adopting a language that is not their own that the irony is undermined.

Here the over-30 will protest: “But I’m using emojis ironically too!” The problem is that irony is a demanding discipline: you have to be ironic in just the right way. Your ironic use of emojis is a little too self-conscious, a little too pleased with itself. It does not achieve the nonchalance, the platonic idea that the mad face is just another keystroke, not in some way cuter or more stylish than mere type.

Of course, many over-30s are probably deploying emojis to communicate with their tweens or teens. I know I have sent my 13-year-old an “😮 😟 😭 ” every once in a while. Or maybe a “GN [Good Night] 💜 💜 ”. This is a craven, even pandering attempt to speak to the natives in their own language, concealing perhaps the slightly disturbing and barely repressed thought that they have ceased to be entirely fluent or conversant in our own. This is understandable, I think, though you are still opening yourself up to eye-rolls, which of course you are also doing by simply poking your head into a room and saying hi. 

***

The problem, a 16-year-old explains to me, is that adults use emojis so literally. Her mother sends her “Good night! 😴 ” or “Can you walk the dog? 🐶 ”. She patiently explains that the humour of emojis lies in the unexpected or random, the detachment from speech, not in a literal translation into pictures. Adults seem weirdly wedded to meaning, to the idea of saying something specific, not blips or pokes. 

The larger issue with over-30 emoji use is that it’s a little too enthusiastic and resourceful. The best thing to do is avoid the far-flung or specific emoji that might imply that you have spent actual time browsing for the perfect or relevant one, or that you have given it any thought at all. The effect of emojis should be almost random, consummately casual, dashed off. A calculated emoji is worse than nearly anything you could do on your phone — or, possibly, in your life. Avoid the whiskey glass and sick face, in other words, at all costs. This is, of course, easier said than done. It is hard for us to resist using emojis like language, searching for just the right one to express what we want to say. We have not yet been able to surrender outdated and old-fashioned notions of communication, ie, that when you reach out to someone you have something specific to say.

I casually mention that I am writing about emojis to my 13-year-old, who says contemptuously, a shade wearily: “That topic is irrelevant to your life.” I am, of course, tempted to text her right then and there: “avocado, whiskey glass, baguette, sick face”. 

The now dispirited over-30 may argue that emojis are fun, which I agree with. They are less fun for teens because they don’t remember, or only foggily remember, a time before emojis. An apple emoji is kind of like an apple in the supermarket — just there. It may, in fact, be the fun we are so evidently having with emojis that is the problem. Perhaps a more bored outlook when you click on 🎉 could help. 

It’s my unscientific observation that dour or sad or bewildered emojis are more dignified than peppy ones. That enthusiasm or joy or love are more treacherous to over-30s than more negative emotions. A negative or melancholy emoji (😞 😢 ) seems more appropriate somehow, less fake or forced, more suited to our bemused relation to this stuff. 

One thing I do cling to is the occasionally effective hostile use of emojis. I recently ended a text with a 😃 to a serious novelist ex-flame who I knew would take this childish and mindless gesture as evidence of the apocalypse and the decline of the English language, and the rise of fascist and lazy internet populism; an attack, in short, on everything he stood for and held dear. He texted back “😃 ??? That’s the best you can do?” And the thing is, it was. It really was. 

Katie Roiphe is the author of ‘The Violet Hour’ and the director of the Cultural Reporting and Criticism programme at New York University

Illustration by Kyle Platts

The FT Mag team would love to hear more from our readers. Have you ever been humiliated by a poor emoji choice? And can emojis ever be dignified for the over-30s? Share your stories and thoughts in the comments below.

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