Many see linguistics as an antiquated field. In the tech age, communication moves so fast that rules of language, even fundamental ones, are regularly broken in the name of brevity and efficiency. It’s tolerated. But that means that this column, to many, is also antiquated, since we all only condemn grammar indiscretions in formal writings.

But in current culture, even our tech tries to help. We all, from time to time, take umbrage with one modern convenience or lack thereof. If you’ve ever used a mobile device with autocorrect, you know that the feature can be both a blessing and a curse. By guessing what you want to say and changing your language, autocorrect was devised to make your communication more efficient. But, as is often the case, it can suggest the wrong word, making your messages confusing, nonsensical, or, worst of all, at least in my eyes, grammatically incorrect.

Autocorrect not only knows common language, but also learns your preferences. For example, my smartphone knows me well enough to suggest that GROBAN be typed in all caps to express my enthusiasm for dreamy singer Josh Groban. On the other hand, my phone all too often goes rogue and makes the wrong suggestion, and I all too often end up sending the wrong word in haste. (Sometimes, I even send the wrong word multiple times in my frantic attempts to correct its first appearance.)

When these mistakes are clearly the result of autocorrect, I don’t mind them much. In fact, they often give me a good laugh. And maybe they give the recipient a good laugh. And the world needs more laughs. When these mistakes imply that I don’t know my grammar, however, they leave me deeply disturbed. For example, my phone has the bad habit of suggesting “its” when I mean “it’s” and vice versa; this may seem like a small error, but to me it sticks out like a capitalized GROBAN.

It is these little errors that have the biggest impact on your reputation, or at least mine as a grammarist. Many autocorrect incorrections are obvious to the recipient—even “autocorrect” has been known to “correct” itself to “auto cucumber.” The other half of the conversation receives that, and laughs ensue. But by removing or adding apostrophes, the sender’s intentions are more in question. “Did he/she mean to type ‘its’? Does he/she not know the difference? I’m not sure.” Just knowing that those thoughts could be happening about me is unsettling—hopefully, it doesn’t bother you as much.

We’ve discussed the difference between “its,” which signifies possession, and “it’s,” a contraction of “it is.” The same mistakes commonly occur between your/you’re and there/they’re/their. “You’re” with an apostrophe is short for “you are,” with the apostrophe replacing the missing “a.” “Your,” on the other hand, is a possessive pronoun. For example, “If you’re going to San Francisco, be sure to wear some flowers in your hair.”

Their/there/they’re is similar. How can you tell the difference between the non-contractions without an apostrophe to point you in the right direction? You may want to remember that “their” ends with an “r,” like its fellow possessive pronouns “your” and “our.” Or, if you have a wacky mind like mine, you may want to remember that “their” is the only member of the there/they’re/their triad that contains an “i,” and both I and their are part of the pronoun family.

While we’re on the subject of apostrophes, I’d like to revisit something I touched on in a previous column: Please, for the love of all who are literate, do not use apostrophes to create plurals. Use them for possessives like “Amanda’s” or contractions like “can’t,” but not for plurals. So, “It’s fun to correct the grammar in President Trump’s tweets,” not, “It’s fun to correct the grammar in President Trump’s tweet’s.” You’ll see this most often when people try to pluralize last names (the Johnsons is correct) or on restaurant menus and marquees. Always a fun game to spot them: “Buy one get two free dessert’s,” for example.

In today’s culture, it may be most important to keep a good eye on autocorrect when you are tweeting. While it’s fun and easy to laugh off a mistake in a text message to a friend, making a mistake in a public post is much more embarrassing, especially if you’re trying to make a point.

And when it comes to subtle distinctions, like the difference between it’s and its, you and you’re, and there/they’re/their, it’s especially important to be vigilant—or at least be prepared to prove you know the correct word if your autocorrect betrays you.


Amanda Jacobs is a grammar expert who worked at 22nd Century Media as chief copy editor and editor for three years. She is currently a public relations specialist at the American Academy of Dermatology.

Previous article

Make One Word Two Again

About the author

Amanda Jacobs is a grammar expert who worked at 22nd Century Media as chief copy editor and editor for three years. She is currently a public relations specialist at the American Academy of Dermatology.

More From Chicagoly

JOIN THE DISCUSSION