Toward the beginning of the 2002 film Secretary, a domineering lawyer (played by James Spader) barges into the office of his assistant (Maggie Gyllenhaal) with evidence of a work infraction: a memo she has written that has “three typing errors.” Spader’s character spits out a reprimand. “Do you know what this makes me look like to the people who receive these letters?”
Setting aside that his screed turns out to be foreplay, Spader’s character was channeling a widespread cultural revulsion: Typos were the ultimate shorthand for careless work. A spelling mistake was proof that the writer hadn’t bothered putting much effort into a piece of correspondence, that their instructions or advice shouldn’t be taken seriously—and perhaps that the recipient shouldn’t invest time in reading their note at all.
More than two decades later, as AI-generated writing has flooded workplaces, social media, and dating apps, old hallmarks of sloppiness—typos chief among them—are getting a new gloss.
Some job applicants are intentionally adding typos to their cover letters to prove that they, and not an AI program, wrote them. Celebrities and CEOs are sending out error-ridden emails and Instagram Stories, and instead of getting a scolding, they are praised for sounding authentic. On some dating apps, where people are, somewhat absurdly, prompted to compose their profiles with AI, typos are apparently no longer an automatic repellant. Nicole Ellison, a University of Michigan professor whose 2006 study showed that dating profiles with spelling mistakes turn people off, now thinks people are warming to the Tinder typo. “A typo maybe signals that you actually do care,” Ellison told Time recently, “because you took the time to write it yourself.” A 2024 study even found that people view customer-service chatbots more warmly when they make and correct errors: A spelling mistake, it seems, is a kind of anthropomorphizing event.
A peculiar reconfiguration of what people consider careless writing is taking place. Although typos and other mistakes don’t suddenly mean that a piece of writing is good or praiseworthy, to some people, they are at least signs that it is worth reading. On a base level, many of us are willing to invest time in reading a long email if we sense that someone actually wrote it, line by line.
In England’s early-modern period, starting around the 1500s, readers understood typos to be inevitable technological blunders. Books were produced collaboratively; writers sent off handwritten manuscripts to printers, who transposed them onto a printing press before setting them to paper. In the process, errors were often introduced.
Authors and editors cataloged these mistakes in “errata lists,” paratextual documents that they slipped into the books after publication—a last-ditch attempt to control the reception of their work. In these documents, they might lambaste their printers to explain the circumstance of mistakes, Alice Leonard, a professor at Coventry University who wrote about typos in Error in Shakespeare, told me. Authors would say, “I wasn’t able to be in the printing house at the time of printing,” Leonard said, or even blame the printer and claim that “the printer was drunk, or the printer was absent, or the printer is useless.” Instead of diminishing the book’s validity, errata lists lent an air of credibility; at least, the thinking went, someone had taken the time to point out what was wrong.
Some writers reveled in printing missteps. James Joyce, whose Ulysses contained more than 200 spelling or grammatical errors in an early edition, called his typos artful experiments in language, “beauties of my style hitherto undreamt of.” By that time, though, he was likely already out of step with his peers: The widespread dissemination of typewriters seemed to recast the typo as a hallmark of individual laziness. With typewriters—and, later, personal computers—printed mistakes became a product of the writer’s failure to read their work closely.
Today, of course, anybody can deliver supposedly clean writing by simply funneling their text through AI, which will churn out a version rife with strangely recurring words (delve), opening interjections (Here’s the thing:), and eerie grammar that’s almost too precise for a typical written exchange. The technological development is prompting people to embrace the old understanding of typos, forgiving misspellings as inevitable errors rather than treating them with scorn.
Even for celebrities, the occasional typo in a public statement is sometimes taken as proof that they are speaking from the heart. This spring, the singer Zara Larsson, who made an offhand remark in an interview that angered Taylor Swift fans, posted a defense in an Instagram Story that included at least two typos (among them a misspelling of physical as psychical). Her statement, free of any trace of a publicist or ChatGPT, came across as sincere. “I like this post because it’s littered with typos,” a host of the celebrity-commentary podcast Who Weekly noted at the time. “You can tell she wrote this herself.”
And no one seems to be accusing Donald Trump of writing his error-ridden Truth Social statements with AI. His press office has suggested that spelling mistakes are evidence of his excellence: A spokesperson for the White House recently told The Wall Street Journal, in response to a question about his frequent typos, “President Trump is the greatest and most authentic communicator in the history of American politics.”
Gone, apparently, are the days when the country’s most powerful leaders are expected to deliver flawless written communications. In an email released with the Epstein files, Peter Thiel called Davos, the Swiss town that hosts the World Economic Forum, “Davis,” according to the Journal. In a text that was made public in a Securities and Exchange Commission filing, Paramount Skydance CEO David Ellison referred to David Zaslav, the CEO of the company he was in the process of acquiring, as “Daivd.” And Jack Dorsey, the CEO of the payment app Block, sent an all-staff email about layoffs without capital letters. Business Insider recently went as far as to proclaim that typos are “the new status symbol” for corporate executives.
These executives may not all be thinking about authenticity; a stray typo could be an innocent flub, or it could simply underscore how little they care. But these moments of textual slippage are oddly refreshing amid the general AI overload. More than half of English-language LinkedIn posts are likely written with AI, according to a study by an AI-detection start-up, and so are many of those “feel good” posts that dominate Instagram and Facebook. A Brookings Institution survey last year of more than 1,000 adults found that 35 percent of respondents with a bachelor’s degree used AI to write or edit documents at work. Peter Cardon, a professor of business communication at the University of Southern California who researches AI in the workplace, has been surveying more than 420 randomly selected “knowledge workers” every six months since 2023. More than half of them, he told me, use AI “at least weekly” to write communications such as emails.
That these AI-generated emails invariably arrive with tidy spelling and grammar does not mean they are warmly received. Office workers have told Cardon that, on a pure prose level, AI-generated emails or project statements are easier to read than the average person’s writing style. Yet, according to Cardon, people are ultimately less likely to act on AI-generated emails. A 2024 Journal of Communication study found that people may engage less with narratives that they think are written with AI—a result that squares with Cardon’s own research about workplace interactions. If an employee suspects that their manager, for instance, is using AI, “they’re less likely to think that person is sincere; they’re less likely to think that person is caring,” Cardon said. “They’re even less likely to think that person is competent.” We know what our colleagues sound like, and we can tell when they send out, say, a thank-you note that they didn’t actually write. So what’s the point of clear prose if you don’t feel any more encouraged by the end of it?
This is not to say that everyone has let go of their rancor for typos. They may still be, to many, a paradigmatic writing sin. But for others, the typo resurgence could be clearing the way for the resuscitation of other, old-school symbols of sloppy writing. Perhaps people won’t turn up their nose as quickly at sentences with extraneous prepositions, verbs that disagree with their subjects, or adjectives where they don’t belong. Maybe overwrought prose or sentences loaded with adverbs will one day draw a little less derision.
Across history, hawkers of new communications technologies have expressed a desire to smooth out and speed up human conversation. But their products have a way of estranging their authors from the final output: Printing presses inserted errors that authors themselves didn’t make, and now AI systems create communiqués that sound nothing like the person sending them.
What many people are starting to look for in written communications, whether they’re from a co-worker or a pop star, is voice. They want to hear the distinct cadences of a CEO, an influencer, or a celebrity, so they can believe that they are reading something genuine. Centuries ago, authors wrote errata lists for the same reason job applicants intentionally place typos in their cover letters today—to resist the universalizing force of new technology, and to prove that there is a real human behind their work.
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