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A red background with a screenshot of a blank email compose box with the AI prompt "help me write" displayed
Have you ever let the machine “help you write”?

InternetFebruary 26, 2025

Never, ever let the machine draft your emails

A red background with a screenshot of a blank email compose box with the AI prompt "help me write" displayed
Have you ever let the machine “help you write”?

Make a habit of using these AI tools, and not only will all your relationships become husks, you yourself will become a husk.

This article was first published on Madeleine Holden’s self-titled Substack.

Recently I witnessed the castration of a furious, spirited man. Maybe you did too. The man’s name was Dale; a character in an ad for Apple Intelligence, an AI-powered writing tool that makes your emails sound Friendly, Professional or Concise with the click of a button. When we encounter Dale, he’s seething, positively ropeable, about the petty theft of his pudding from the office fridge. It’s clear we’re meant to read Dale as being a prissy little bitch, with his stiff collar, neat moustache, and fussy mannerisms, but there’s nothing limp-wristed about the tirade he bashes out on his MacBook keyboard. “To the inconsiderate monster who has been stealing my pudding,” he begins, “I hope your conscience eats at you like you have eaten my pudding.”

Dale pauses doubtfully before clicking send, glancing at a “FIND YOUR KINDNESS” T-shirt on a nearby teddy bear. After he selects Apple Intelligence’s Friendly mode, Dale’s searing tirade is rendered into limp corporate speak. The new tone-adjusted message kicks off with “Hey there”, neuters lines like “That pudding was my only light in an otherwise bleak corporate existence” into “You see, snacks are a big deal in our company”, and rounds off with an insipid, “Thanks for your understanding.” His pudding is returned by the woman who stole it. Dale eats an ecstatic mouthful. He “wins”.

The ad is meant to be funny, but there’s no irony whatsoever about that last point: that by capitulating to Friendly mode, Dale “wins”. Any red-blooded viewer can see his life-force being drained from his eye sockets; you get the sense this short film is winding up to a Clockwork Orangestyle meditation on the creepiness of social engineering wrought by AI. But it isn’t. It’s an advertisement for AI. It isn’t meant to be blood-curdling, it’s meant to have you laughing all the way to the Apple Intelligence software update: the sooner you start Friendlifying your emails, the better! That this bland, eunuch prose is actually good is taken as read.

I assume everyone but the most bloodless tech shills views this development as a horror, but I’m not sure: I don’t go on social media anymore, so if there was a wave of backlash, I missed it. But waves of backlash give me no comfort these days anyway. This isn’t my first rodeo.

My first rodeo was in 2018. Smart Replies — those three brisk, easy-click, AI-generated reply options autopopulated under certain emails — were being rolled out as standard on all Gmail accounts (as well as the Smart Compose function, which predicts the end of your sentence as you type). Smart Replies were widely derided as insulting and creepy, on social and traditional media alike, and their jaunty, discordant tone roundly mocked.

Some journalists briefly grappled with the broader interrelational, intellectual and spiritual stakes of giving in to this technology. “I have wondered whether saving a few seconds of not having to type ‘ok, sounds good’ is worth letting a robot mediate my interactions with other humans,” wrote Mashable reporter Rachel Kraus. “Or if the impulse to hit a button instead of form a thought could in some way stymie my own expression, even in rote communications.”

In the end, though, Kraus said she couldn’t decide. Elsewhere, resignation prevailed. In 2018, the Wall Street Journal reported that Smart Replies already constituted 10% of all messages sent over Gmail. After deriding them as inhuman in the New Yorker, Rachel Syme wrote: “At some point, I started giving in to the Smart Reply robots from time to time, and something strange happened. I didn’t hate it.”

Reading back over this coverage today, I find the lack of conviction maddening. Over and over, writers betrayed an intuition that something was deeply wrong with Smart Replies — that the machines were starting to remodel us in their own “ghastly image” — then they cracked a weak joke, shrugged and moved on, or started using them. None of these writers were shrill or hysterical, none made an urgent moral case, none raised their voice. None of them, in other words, sounded like Dale. And now Dale has no balls.

Why are so many people so sanguine about the robot takeover of our emails? Probably because of how passionately we loathe our inboxes: the relentless onslaught of messages (74 per day, on average), their tone of false cheer, and the fact that so many come from people we hold in mild contempt — managers, real estate agents, spin doctors, if they come from people at all — yet we’re obliged to spend huge chunks of our allegedly wild and precious lives dealing with them. Even for people creeped out by the prospect of using AI tools like Smart Replies, ChatGPT and Apple Intelligence to compose their communication, the offer sounds too good to refuse.

But it was obvious from the outset that the machine wouldn’t stop at the domain of work, and would soon come for the domain of love. Here’s the British writer Sam Kriss at the end of 2023, with a half-joking prediction that robots would soon take over our more intimate online realms:

You don’t hang out with your friends any more, but you have a group chat. Increasingly, your messages to your group chat will be written by AI. The machines will communicate for everyone in the same friendly, even tone, and everyone’s group chat will contain the same roster of mildly funny memes. You will look at them and feel nothing, and push a button to generate your response. Ha! That’s so funny, Dave! You’re the Meme King!

You don’t meet people any more, you use online dating. Increasingly, your conversations with prospective lovers will be written by AI. Your machine will generate banalities at her machine, about tacos and The Office and pineapple on pizza, and her machine will do the same, until it’s time for her to autogenerate a nude. You will look at it and feel nothing, and push a button to generate a response. Wow you’re so sexy. And then, having never spoken to each other before, you will never speak to each other again.

Now, we have real-time examples of this exact nightmare unfolding. Last month, for instance, a woman posted on Reddit to a screenshot of a “heartfelt” text message her boyfriend sent her for her birthday, clearly generated in its entirety by AI. She reports, quite naturally, feeling offended and sad. But note her primary inquiry to the Reddit forum: am I overreacting? For some commenters in the thread, the answer is yes.

a screenshot of a reddit post where a woman asks about her boyfriend's birthday message. the message is long and clearly written by AI

How did we slide into this “boring dystopia”, this “unlivable techno-dump”, in which robots communicate for us while we sit by, drooling? And why didn’t we resist?

Let’s set aside people who truly see no problem with the birthday message above, the AI defenders wheeeee-ing down the slide to the techno-dump. Let’s consider the moderates, cautiously gripping the sides. When I listen to them speak, they insist on two key points: one is that any brain damage caused by using AI communication tools can be safely contained by limiting its use to certain circumstances: I only use Smart Replies when I’m really busy. I use ChatGPT to draft my work emails, but I’d never use it to text a friend.

Two, they insist that human qualities ultimately prevail: AI gives me a draft, which I tweak as I see fit. All it does is help me get over the inertia and dread of facing a blank compose box, then my human judgement and skill kick in. I still care about the person on the receiving end of my message.

This is all wrong. To assume nothing is lost when humans are freed from the inertia and dread of facing a blank compose box; to believe you can still care for people after you stop performing the small, quotidian actions that constitute care; to delude yourself that your good qualities will remain stable if you give up the very work that forges your character: it’s all wrong. There is no safe container for AI communication, no acceptable use case, not even low-stakes work emails to people you hate. Make a habit of using these tools, and not only will all your relationships become husks, you yourself will become a husk. The stakes couldn’t be higher. To see why, we need to return to Dale’s office.

Dale is an AI moderate. He would never use ChatGPT to draft a lover’s birthday text, but he’s happy using Apple Intelligence to smooth out aggro work emails about stolen puddings, and he makes frequent use of Smart Replies. He has to! He gets so many emails.

Dale works as a communications officer for a large logistics and transport corporation — a day job he hates, with coworkers every bit as tedious as the work — but on the side, he helps edit a small literary magazine, work that truly sets his heart ablaze. Dale has three Gmail addresses, one for his day job, one for the magazine, and one personal, but to streamline his communications he has them all directed to a single inbox — the inbox he’s facing with increasing dread on this Tuesday morning in the office.

Paralysed by 74 new messages, plus 26 read emails from previous days and weeks he’s determined require a response, Dale begins answering around a third of the new emails using Smart Replies — the low-stakes stuff: unsolicited emails from publicists and real estate agents, trivial life admin, pointless to-and-fros with his manager. He’s aware, somewhere at the back of his mind, that this embroils him in a Whack-a-mole game of ever-proliferating emails: the faster he replies, the more dizzying the game becomes. But he hits the Smart Reply button anyway, batting away a nagging set of questions at the same time: why are my manager and I swapping Smart Replies when we work in the same room? Why don’t people pick up the phone any more? Why are some of the best minds of my generation sending pointless emails all day long? Why is pudding my only light in an otherwise bleak corporate existence? Why am I living like this? And why don’t I resist?

Existential questions swatted away, Dale turns with dread to the 26 read emails languishing in his inbox. These are thorny emails of much greater consequence, the ones Smart Replies can’t help him with. He reopens one containing a poem by an unknown young woman submitted for publication by the magazine he edits. The poem lays bare a deep personal wound; detailing the woman’s date rape at age 17. The poem is overwrought, unpublishable, just plain bad. This woman had such guts to pen something so raw, but she’s got so much to learn about crafting poetry. Dale hopes she keeps writing. He needs to reject her submission, but he wants to do so without crushing her spirit.

The other 25 emails are similarly sensitive and difficult, for their own set of reasons, and Dale’s decided he needs to answer them all today. But he doesn’t know what to say. He can’t get started. He’s paralysed. The clock is ticking. He needs help.

Dale considers that ChatGPT could move him past this impasse. He feels uneasy about using AI to deal with sensitive emails: the last thing he wants is to end up like the dean of Vanderbilt University, sending a platitudinous, AI-generated email in the wake of a mass shooting. But as the machine spits out a surprisingly polite and humane set of words for Dale to lightly edit and send off to the aspiring poet, his trepidation lifts, and another set of questions at the back of his mind stops nagging so loudly, namely: who is this person that’s emailed me, and what do I owe them? Is it my job to save a new writer from the sting of rejection? Is it worse to be blunt or fake? What are the costs of saying the wrong thing? What are the costs of always being paralysed by fear of saying the wrong thing? What should I say?

a white screen with a polite rejection email written by AI with gaps left for the 'writer' to add a name of the recipient

Why is the AI-generated rejection letter or birthday text so dehumanising? Think about what it means to treat someone well: fundamentally, it involves considering who they are, what they might want and need, and whether you can help. This can be difficult, maddening work, because other people are such puzzles: strangers are a mystery, obviously, but even with loved ones, all we ultimately have to go on is some theory of mind and a few clues about their ever-changing set of likes and dislikes. So “considering” is the operative word: we have cliches like “it’s the thought that counts” because we recognise that the process of thinking about, considering, puzzling over another person is what actually constitutes care, not the flashy gift or perfectly crafted message that results. When you outsource the thinking to AI, you outsource the care. Your communication becomes empty, and your relationships hollow out.

But so do you. Whenever you are facing a blank compose box, filled with dread and inertia, you are being presented with a small, quotidian opportunity to strengthen your character. Whether it’s a birthday text, rejection letter, or quick reply to a dumb message from your manager, the resistance is always telling you something useful. This is the stuff that really matters. This shit doesn’t matter at all.

It takes courage to decline your manager’s waste-of-time request. It takes tact and sensitivity to draft a good rejection letter. It takes wisdom and perspective to decide to ignore unsolicited emails from publicists and real estate agents. When you use AI as a crutch, always at the ready with a suitable set of words — when you bypass the resistance and bat away those deep nagging questions — you deprive yourself of an opportunity to be brave, tactful and wise. Do this over and over, and your bravery, tact and wisdom will atrophy. Your character will corrode.

This is why AI communication tools can’t be safely contained by limiting their use to certain circumstances, like bullshit work emails: there is no sphere of your life where this chipping away at your character doesn’t cost you. Making a habit of using these tools also means missing a vital lesson, which is that failure is salutary. It moulds you beautifully to fuck up and say the wrong thing, or fail to say anything at all, and notice the pain this causes. Or the surprising lack of pain it causes — the maddening array of responses it elicits in different people. Alice respects a prompt, blunt rejection email; Miles goes to pieces over it. What do you do with this? I send Alice prompt, blunt rejection emails, and spend weeks crafting ornate and soothing missives to Miles. Or: I send prompt, blunt rejection emails, whoever you are, come what may, because that is who I am.

Machines have a place, and there is drudge work we should hand to them. Let them wash your filthy clothes and drill holes in hard earth. But not this. Never this.

This article was first published on Madeleine Holden’s self-titled Substack.

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A black background with a white 'X', the social media platform logo, and Elon Musk and JD Vance's portraits on either side
Elon Musk and JD Vance are utilising Muks’s X platform for their causes

OPINIONPoliticsFebruary 26, 2025

We are in an information war – and we are losing

A black background with a white 'X', the social media platform logo, and Elon Musk and JD Vance's portraits on either side
Elon Musk and JD Vance are utilising Muks’s X platform for their causes

If there is one hard lesson we in New Zealand know all too well, it’s that when hate spreads online, it doesn’t stay there. 

There’s an information war going on in the world right now. And we are losing.

Elon Musk and Donald Trump, supported by an army of bots, grifters, liars, and complicit and compromised politicians on both sides of the aisle, have managed to aim true and strike a blow to the heart of liberal democracy and the rules-based international order. 

Right now on social media platform X (formerly Twitter), its owner Elon Musk and Vice President JD Vance are signaling intent to defy increasingly strident court orders. Their weapons of choice in this war are data, the widespread manipulation of public opinion, and the use of internet mobs to attack critics. 

Liberal democracies like our own here in New Zealand – and like the one that the United States was until very recently – are extremely vulnerable to information warfare. I know because I have been running a programme that educates people to apply skills that have been proven effective in countering disinformation. These aren’t regulatory approaches, but rather techniques that everyone needs in order to “do their own research” –and that all institutions need to manage a complex information environment. 

In doing this, I’ve been fortunate to work with a variety of funders, from pre-Musk Twitter to the New Zealand government – and most recently the US Embassy in New Zealand. Following the inauguration of Donald Trump and his chaos-inducing executive orders, we mutually agreed to terminate the grant funding our A Bit Sus Pacific Media programme. The independence of our education programme and our commitment to the privacy of our students made the arrangement unviable for us. And the Embassy’s obligation to follow the orders of Donald Trump made it unviable for them. 

New Zealand’s laudable commitment to freedom of expression, of the press, and of association leave us reasonably reluctant to fight back in ways that protect our political and social cohesion. This reluctance is present even when we know that the attack is coming from nation states whose interests don’t align with ours or from oligarchs intent on steamrolling our democratic processes and institutions. 

At this moment, New Zealand is in a place of extreme vulnerability. Even now we can see online the drumming up of support for our own version of DOGE (the so-called ‘Department of Government Efficiency’, which in reality is  a billionaire-led impoundment of tax dollars and money Congressionally allocated to ensure the public good) which on our shores would also represent a Treaty violation that would resonate through our social fabric in ways hard to imagine. 

Led by Musk, but devolving to his online swarm, any person or organisation who happens to meet their glance is at risk.  The University of Auckland has been the most recent target of this kind of attack, but they aren’t the only victim, and they will not be the last. 

These are the tactics of totalitarianism and authoritarianism. 

Elon Musk's face edited over a picture of Pope Francis, with a dogecoin meme in place of the eucharist
Elon Musk and his beloved dogecoin. (Image: Reddit)

We are a small country whose economic prosperity and security relies on a stable rules-based international order. Without that, we are vulnerable. Facing the elephant in the room – the sudden collapse of the United States out of liberal democracy – compels us to reassess what we are doing to prepare our people and our institutions in this war of information. 

The attacks from people like Musk are not based on truth. They often contain a kernel of fact, but the big lie is embedded in the framing – that is, the lens through which we see the world and understand it. Disinformation actors work to build frames as narratives through which they can channel their stories and manipulate public opinion. 

As someone who has spent the past few years teaching the kinds of skills that internet users can deploy to avoid falling prey to disinformation, I frequently get asked why these tactics cannot be used for good, to protect people’s freedoms and build support for pro-social issues like the protection of the environment. 

The answer is that false frames can be built in ways that are simply more compelling than real life. Conspiracy, hate, and constant drama are the hallmarks of how disinformation actors pull people in and keep them engaged. They leave those enmeshed in these narratives riled up and energised for the next part of the story and not inclined to engage in the often routine and plodding work of creating change through the institutions and structures of a democracy – or a Treaty partnership, for that matter. 

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Gabi Lardies
— Staff writer

You can see the result in the so-called “Blue MAGA” movement, a Democratic Party mirror-image of the movement Trump built. While the target of the narrative is different – usually Republicans and the familiar red-hatted MAGA adherents – the shape and impact of the hate is the same. Hate is hate and it cannot be twisted to good purpose. 

And that’s the key to countering disinformation while respecting the vital freedoms we hope to continue to enjoy. The evidence is quite compelling that what works to rein in these attacks and support resilience to them across the population has nothing to do with censorship, restricting freedom of expression, or even regulating online platforms. Those solutions are not viable and are rapidly failing even in Europe. 

Rather, investment and energy placed into a programme of warning people about false narratives, teaching people how to fact check themselves, and supporting high standards of discourse and behavior – especially from political leaders – is what works. 

Those who lived through the great conflagrations of the 20th century are almost all gone now. New Zealand suffered terribly through those, when all hell broke loose in the world. 

Today, Donald Trump’s unhinged threats against Canada, Panama, Greenland, and Gaza are not idle, and it would be irresponsible of us and our leaders to assume they are – or to assume that the consequences of an expansionary America would not come to rest at least in part on our shores. 

We cannot allow ourselves to lose the information war. Maintaining the legitimacy and health of our democracy is the most important issue we face. All others rest upon it. 

The world is at war again now and it is unlikely to remain online. If there is one hard lesson we in New Zealand know all too well, it’s that when hate spreads online, it doesn’t stay there. 

Refusal to secure our information sphere is a refusal to secure our country. It’s time that all of our political parties face up to that and act. We don’t have much time left before it really is too late.