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Vindicated At Last In My Years-Long Loathing Of Grammarly

Defector | The last good website. [Unofficial] March 13, 2026
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I first learned about the AI writing assistant Grammarly nearly a decade ago, when their YouTube ads suddenly sprang into ubiquity, clinging to my precious videos like a swarm of spotted lanternflies. At first this seemed innocuous, the high-pitched whine of a buzzy new startup that would soon fizzle into obscurity. Mostly I was confused by their gargantuan ad budget. I was not alone. But the ads never relented, and as I was served unskippable Grammarly ads again and again, the script seared into my brain: "Writing's not that easy, but Grammarly can help." The ads irritated me so much that, on principle, I tried to coat my brain in teflon and slough off any and all information about Grammarly's whole deal, which meant that I barely registered what, exactly, the company did. But even back then, before I had any real reason to, I knew then that I hated Grammarly. Grammarly, which was founded in 2009 and rebranded as Superhuman last fall, used tools like machine learning to proofread people's writing. It checked grammar and spelling, similar to Microsoft's Office Assistant, albeit with none of Clippy's signature panache. If Grammarly's ads were to be trusted, it was perfect for people like Tyler, who needed Grammarly's help to write an email to his boss Anita. In that commercial's logic, Tyler wants Anita to like him, but he doesn't want to sound unsure of himself. So Grammarly helps him swap words like "really helpful" to "beneficial" and "educational" to "informative," words, we are told, that will connect better with Anita. Tyler's successful email means Anita emails him back in just a few minutes, and they can now ride the elevator together standing close to each other. Each time I was forced to watch this ad, I remember wondering: Are Tyler and Anita going to smash? That product appeared somewhat benign, considering the wretched contemporary landscape of overtly malevolent tech companies with even more discomfiting ads. But not to be outdone, in 2023 Grammarly introduced generative AI assistance, which, among other things, offered to now do the writing for you. In the years following, the company expanded its suite of generative AI fripperies, with features such as "AI Instagram Caption Generators" or a feature called "Improve It" that offered to "make" a piece of writing any of the following adjectives: diplomatic, exciting, inspirational, friendly, empathetic, assertive, confident, or persuasive. This all sounded like stupid, run-of-the mill gen-AI bluster.

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