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The 13 Trickiest Grammar Hang-Ups

Even the best of us can stumble over rough grammar patches now and then. Grammar Girl shows you how to navigate 13 top trouble spots.

I trust that you all know the difference between who and whom, and I trust that typos are the only reason you use the wrong it’s. It happens to the best of us. For most writers, if you can just maintain your focus (perhaps with caffeine and frequent breaks), you’ll get the basics right. The following problems, however, may have you scrambling for a refresher.

The 13 Trickiest Grammar Hang-Ups

1. Half can be both singular and plural.

Typically, subjects and verbs agree: If the subject is singular, the verb is singular. If the subject is plural, the verb is plural. Easy peasy. However, sentences that start with half don’t follow this rule.

Half alone is singular: My half of the pizza is pepperoni. Yet although half is the subject in a sentence such as Half of the pizzas are missing, we use a plural verb because of something called notional agreement. It simply means that although half is singular, half of the pizzas has a notion of being plural, so you use a plural verb. Follow this rule when half is the subject of a sentence: If half is followed by a singular noun, use a singular verb. If half is followed by a plural noun, use a plural verb. Half of the pepperoni is ruined, but half of the tomatoes are missing.

Compound words that start with half are quirky too. They can be open, closed, or hyphenated (e.g., half note, halfhearted, half-baked). There’s no rule that applies across the board, so you’ll have to check a dictionary.

The 13 Trickiest Grammar Hang-Ups

2. Companies are not exactly people.

Companies are entities, but they are run by men and women, so you could make an argument for referring to a company as who, particularly since U.S. courts have ruled that companies are people in most legal senses. Nevertheless, the standard style is to refer to a company as an entity and use the pronouns it and that: We want to buy stock in a company that makes hot air balloons.

If you want to highlight that people in the company are behind some action or decision, name them and use who: Floating Baskets was driven to bankruptcy by its senior directors, who took too many expensive Alaskan joyrides.

3. American is a flawed term.

American is the only single word we have to refer to citizens of the United States of America (U.S.-icans?), but technically, an American is anyone who lives in North America, Central America, or South America.

In the U.S. we, the people, have been calling ourselves Americans since before our country was even founded (as have our detractors). Although all people of the American continents are actually Americans, most readers in the U.S. and Europe assume that an American is a U.S. citizen, since that is how the word is most commonly used.

Despite its failings, use American to refer to a citizen of the United States of America. No better term exists. Feel free to feel guilty.

(12 Most Popular Grammar Questions and Answers on

4. The word dilemma can be, well, a dilemma.

The di- prefix in dilemma means “two” or “double,” which lends support to the idea that dilemma should be used only to describe a choice between two alternatives. The Associated Press Stylebook and Garner’s Modern American Usage not only support that limitation but go further, saying that dilemma should be used only for a choice between two unpleasant options.

Nevertheless, Garner also notes that other uses are “ubiquitous.” Merriam-Webster’s Dictionary of English Usage and The Columbia Guide to Standard American English say it’s fine to use dilemma to describe any serious predicament, and The American Heritage Guide to Contemporary Usage and Style takes an intermediate position. What’s a writer to do? (Is it a dilemma?)

Unless you’re writing for a publication that requires you to follow a style guide that limits dilemma to a choice between two bad options, it’s not absolutely wrong to use dilemma to describe a difficult problem, even when alternatives aren’t involved, or to use dilemma to describe a difficult choice between pleasant options. Still, you’ll seem most clever when you use dilemma to describe a choice between two bad options. In other instances, before using dilemma, ask yourself if another word, such as problem, would work better.

Also, a cursory search of the Internet reveals that lots of people are confounded by the spelling of dilemma. Many were taught to spell it wrong. In fact, I was taught to spell it dilemna in school, and when I got older and checked a dictionary, I was shocked to find that the word is spelled dilemma. Further, the only correct spelling is dilemma. It’s not as if dilemna is a substandard variant or regional spelling. Dictionaries often note alternative spellings and sometimes even nonstandard spellings, but dilemna doesn’t even show up that way. As far as I can tell, nobody knows why so many teachers got it wrong. Perhaps a textbook typo is to blame.

5. Earth isn’t treated like the names of other planets.

In English, the general rule is that we capitalize the formal names of things and places (e.g., Golden Gate Bridge, San Francisco), so we capitalize the names of other planets: Jupiter, Mars, and so on. For some unknown reason, however, we treat earth differently. Sometimes it’s capitalized and sometimes it’s lowercase, and there doesn’t seem to be a hard-and-fast rule.

Typically, when earth is preceded by the, it’s lowercase, and when earth is listed with the names of the other planets, it’s capitalized—but you can find exceptions to even these patterns. (Of course, when we’re just using earth as another word for dirt, it’s always lowercase.)

If you’re a writer, check your publication’s style guide to see what it recommends. If you’re writing for yourself, the most important thing is to be consistent—so just pick a capitalization style and stay with it.

(Remove That From Your Writing (Grammar Rules))

6. Gone missing might be annoying, but it isn’t wrong.

Gone missing is a Briticism that has made its way to the U.S., where reporters use it mostly to describe missing persons. Although journalists and newscasters seem to love gone missing, it’s easy to find vocal readers and viewers who hate it.

Haters argue that a person must go to a location, and missing isn’t a place, and that an inanimate object can’t go missing because it can’t take action alone—but English has never been so literal. In a tight labor market, jobs can go begging (be unfilled), for example, even though begging is not a location and jobs can’t take action. Other peevers suggest that gone missing necessitates an action on the part of the person or item that has vanished. Again, we have parallels that undermine the argument: Milk goes bad, for example, without taking any action on its own.

Gone missing is not wrong. The Oxford English Dictionary places it in the same category as the phrase go native, as in, We had high hopes for our new senator, but after he was in Washington a few months, he went native (i.e., adopted the same habits and attitudes as people who’ve been there a long time).

Even if you hate gone missing, you can’t legitimately criticize it as grammatically incorrect. But on the flip side, if you’re a fan of the phrase, be aware that it annoys enough readers that you should think twice before using it in your writing.

7. Kinds is always plural.

You have one kind of peanut butter but three kinds of jelly. Use the singular (kind) when you have one of something, and the plural (kinds) when you have more. Since these and those indicate multiple things, you have to use a plural: kinds. These kinds of situations always perplex me. (These kind is wrong.)

Watch out for the problem. Even though it seems straightforward, good writers often get it wrong.

(Are Subjects Joined by "And" Singular or Plural? - Grammar Rules)

8. Until is ambiguous.

If you have until March 4 to submit an entry in the National Grammar Day video contest, does that mean you can still turn it in on March 4, or is March 3 the last acceptable day? Unfortunately, the word until doesn’t make the meaning clear. People can interpret it different ways.

One of the most stress-inducing deadlines is the annual tax filing cutoff for the Internal Revenue Service, which makes a point to specify that the April 15 filing deadline includes April 15. It also refers to April 15 as a due date, not a deadline.

If you’re following instructions, don’t assume until means through. Turn in your item a day early or get clarification. And if you’re writing instructions, make them clear by using a word such as through or stating a specific day and time. The IRS doesn’t rely on an ambiguous word such as until, and neither should you.

9. Next is also ambiguous.

Just like until, next is ambiguous: Some people think next Wednesday means the next Wednesday that will occur, and other people think next Wednesday means the Wednesday in the next week, regardless of what day it is now. The sitcom Seinfeld even did a scene in which Jerry and Sid argued about the meaning of next Wednesday versus this Wednesday.

There is no definitive meaning for next Wednesday, so you should avoid using next to modify a day of the week. Be more specific in your writing.

(When Do I Spell Out Numbers? (Grammar Rules))

10. The plurals of abbreviations aren’t always logical.

Acronyms are abbreviations that are pronounced as words (NASA), and initialisms are abbreviations for which you say each letter (FBI).

Even though it doesn’t make perfect sense, you make initialisms and acronyms plural by adding an s to the end no matter what part would be plural if you wrote out the whole thing. Therefore, even though you would write runs batted in, the plural is RBIs.

In the past, some publications used apostrophes to make acronyms and initialisms plural, so until a few years ago, it was common to see something like RBI’s or CD’s in TheNew York Times. But these days, the major style guides recommend omitting the apostrophe.

11. They and their may soon be acceptable singular pronouns.

English has a big, gaping hole: There’s no pronoun to describe a person when we don’t know the sex. (I’ve tried it with babies, and it hasn’t gone over well!) In days gone by, he was acceptable as a generic pronoun, but today it’s not. All major style guides recommend against it.

To fill the gap, many people consciously or subconsciously use they, as in, Tell the next caller they win a car. Doing so is allowed by some current style guides and actually has a longer history than most people realize. Even Jane Austen did it. For example, here’s a quotation from Mansfield Park in which Austen pairs a plural pronoun (their) with a singular antecedent (each):

Everybody around her was gay and busy, prosperous and important; each had their object of interest, their part, their dress, their favourite scene, their friends and confederates: All were finding employment in consultations and comparisons, or diversion in the playful conceits they suggested.

Although many people consider using they as a singular pronoun wrong, I suspect many of those same people use it that way in casual conversation without even realizing it, and that the singular they will become fully acceptable within the next 50 years.

Today, using they as a singular pronoun borders on acceptable. You can choose to do it if you aren’t bound to follow a style guide that opposes it, but be prepared to defend yourself. The safer route (when you can’t just rewrite the sentence to make the subject plural) is to use he or she, or to switch between he and she (which you may have noticed is the style followed by this very magazine).

When switching between he and she, however, make sure you separate the examples enough so that you don’t confuse your readers. (Weren’t we just talking about a woman?) Also, I’ve recently started getting complaints from men who’ve noticed that writers switching between he and she tend to use he for the bad guys and she for the heroes. If you’re going to switch back and forth, give us some vixen ax murderers and hunky human-rights activists every once in a while.

(Toward vs. Towards (Grammar Rules))

12. Possessives of possessives can get messy.

When you have to make a possessive name possessive, you’re technically supposed to add another possessive marker to the end:

Kohl’s’s earnings were up last quarter. (TheChicago Manual of Style possessive style)

Kohl’s’ earnings were up last quarter. (TheAssociated PressStylebook possessive style)

Avoid these kinds of sentences, though. They may be technically correct, but they look horrible. You can usually rewrite the sentence to make it better:

Kohl’s reported higher earnings last quarter.

13. Apostrophes can occasionally signify plurals.

We all cringe when we see a greengrocer’s apostrophe (banana’s $0.99), but did you know that in a few uncommon instances, we do use apostrophes to make things plural? In most cases, the apostrophe helps avoid confusion; single letters are one example. The first apostrophe in Dot your i’s and cross your t’s helps readers distinguish between multiple copies of the letter i and the word is. A less logical example is the phrase do’s and don’ts. Different style guides recommend different spellings (dos and don’ts, do’s and don’ts, and do’s and don’t’s). When writers use an apostrophe to make do plural but not to make don’t plural, the only reason for the apostrophe is to provide visual balance. Yet, it’s allowed.

Grammar and Mechanics

Do you remember the difference between the 8 parts of speech and how to use them? Are you comfortable with punctuation and mechanics? No matter what type of writing you do, mastering the fundamentals of grammar and mechanics is an important first step to having a successful writing career.

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