Apostrophe Rules

Apostrophes can be tricky. Sometimes they form possessives. Sometimes they form contractions. Can they ever make something plural?

Apostrophe Use: Contractions and Omissions

A contraction is a shortened form of a word (or group of words) that omits certain letters or sounds. In a contraction, an apostrophe represents missing letters. The most common contractions are made up of verbs, auxiliaries, or modals attached to other words: He would=He’d. I have=I’ve. They are=They’re. You cannot=You can’t.

Some writers use less common contractions when they want to represent a particular style of speech. They might write somethin’ to represent the way people often don’t pronounce the final g of “something” in speech. Occasionally, you might see e’er (instead of ever) in poetry. And, of course, in the American South, you will probably encounter y’all (you all). Decade names are often contracted as well: the ’60s (the 1960s).

Contraction	Uncontracted	Examples
-n’t	not	Isn’t (is not), hasn’t (has not)
-‘re	are	They’re (they are), we’re (we are), you’re (you are)
-‘d	had, would	She’d (she had, she would), I’d (I had, I would)
-‘ll	will	We’ll (we will), you’ll (you will)
-‘s	is	He’s (he is), it’s (it is)
I’m	I am	—
let’s	let us	—

Contractions are usually considered to be relatively casual. If you’re writing something very formal, you may want to avoid using them except in cases like o’clock, where the full phrase (of the clock) truly is rare.

Apostrophes and Possessive Nouns

The rules about forming possessives probably cause the most apostrophe confusion. They vary a little bit, depending on what type of noun you are making into a possessive. Here are the rules of thumb:

For most singular nouns, add apostrophe+s:

The dog’s leash The writer’s desk The planet’s atmosphere

For most plural nouns, add only an apostrophe:

The dogs’ leashes (multiple dogs) The writers’ desks (multiple writers) The planets’ atmospheres (multiple planets)

For plural nouns that do not end in s, add apostrophe+s:

The children’s toys The geese’s migration route

Style guides vary in their recommendations of what to do when you have a singular proper noun that ends in s. Some recommend adding only an apostrophe:

Charles Dickens’ novels Kansas’ main airport

Others say to add apostrophe+s:

Charles Dickens’s novels Kansas’s main airport

No matter which style guide you use, add only the apostrophe to plural proper nouns that end in s:

The Harrises’ house The Smiths’ vacation

Use whichever style matches the style guide you use for your writing. If you don’t have a style guide, it’s OK to just pick one of the methods, as long as you don’t switch back and forth within the same document.

Apostrophes and Possessive Pronouns

Personal pronouns, unlike regular nouns, do not use apostrophes to form possessives. Most writers don’t have trouble with the possessive pronouns my, mine, his, her, and our.  It’s your, yours, hers, its, ours, their, and theirs, that tend to cause the confusion. The relative possessive pronoun whose is also frequently the victim of apostrophe abuse. Note that none of these forms uses an apostrophe. In fact, for some of these pronouns, adding an apostrophe forms a contraction instead of a possessive (see the table above).

Pronoun	Possessive Pronoun	Absolute (Independent) Form
Me	My	Mine
You	Your	Yours
He	His	His
Her	Her	Hers
It	Its	—
We	Our	Ours
Them	Their	Theirs
Who	Whose	—

How to Write Joint Possession

What do you do with the apostrophe when you’re talking about things that belong to more than one person? When one thing belongs to two or more people, make only the final name possessive:

Bob and Jim’s bait shop (Bob and Jim co-own the same bait shop) Ryan, Jessica, and Elinor’s parents (All three share the same parents)

When you’re talking about separate things that belong to different people, make all the names possessive:

Bob’s and Jim’s bait shops (Bob owns one bait shop and Jim owns a different one) Ryan’s, Jessica’s, and Elinor’s parents (Each has a different set of parents)

Using possessive personal pronouns in joint constructions often sounds awkward (You have their and my gratitude). Usually, the best solution is to rephrase the sentence to avoid the joint construction (You have our gratitude or You have their gratitude and mine).

Apostrophes and Plurals

Using an unnecessary apostrophe to form the plural of a noun is a very common mistake. Sometimes, it’s called the grocer’s apostrophe because of how frequently it is spotted in grocery store advertisements (3 orange’s for a dollar!). Don’t do it! With very few exceptions, apostrophes do not make nouns plural.

The one notable exception to this rule is the plural form of lowercase letters, which are formed with an apostrophe to prevent misreading:

Don’t forget to dot all your is.

Don’t forget to dot all your i’s.

Apostrophes with Surrounding Punctuation

An apostrophe is part of the word it belongs to, so it should not be separated from the word by periods, commas, question marks, or any other punctuation mark.

Can I ask you somethin’? “’Twas the night before Christmas,” he said.

In the second example, take note of the apostrophe at the beginning of ’Twas. Apostrophes that fall at the very beginning of a contraction are often mistyped as left-hand single quotation marks. Word processors tend to do this by default. Keep this in mind, especially when you are writing about specific decades, such as the ’60s or the ’90s.

When to Check a Style Guide

Sooner or later, you’ll come across a phrase that sounds fine out loud but looks weird on paper because of the apostrophes. Do’s and don’ts? Dos and don’ts? Do’s and don’t’s? For cases like these, it’s best to check a comprehensive style guide, such as the Chicago Manual or the AP Stylebook (it’s do’s and don’ts, according to the AP). A good dictionary may also be able to offer you some guidance. If you can’t find a precedent, it’s probably best to use a different word or phrase; overly creative apostrophe use will inevitably distract your readers.

How to Make a Clear, Assertive Point Over Email

Giving someone a lot of work to do, taking on a new responsibility, asking for leeway, requesting a favor, disagreeing with someone, expressing a strong opinion, or just saying hi after a long radio silence—these topics are tough in conversation, and when you’re trying to broach a difficult subject over email, there can be even more at stake.

Grammarly has put together a guide of best practices for sending emails on difficult topics without coming across as aggressive, demanding, or rude. When the time comes for you to send such an email, make sure you take AIM.

What is AIM, you ask? It’s all about your Audience, Intent, and Message. It’s a useful tip for strategic communications in general and can come in extra handy when you’re writing an email with an unpleasant message, big request, or general bad news for your recipient.

Audience: The Big Picture

When you fire away email after email on a daily basis, you’re probably not thinking too hard about the hopes and dreams of every person you’re writing. But for the big, tough messages you have to send, take some time to think about your recipient and about using email to make your point.

Make sure email is the right medium for the message

With email, you have plenty of time to think through your message and carefully choose your words. However, you don’t get that human element that can make all the difference in some difficult interactions. Talking in person gives you the tools of tone of voice, facial expression, and body language. If you’re giving bad news, you can show that you’re sympathetic. If you’re asking for a raise, you can project confidence. Some conversations should take place in person.

That said, it’s also possible to craft your writing in a way that shows you’re a thinking, caring human—but it takes work. If you use email, choose your words carefully to convey the right tone to go along with the content of your message.

Know your recipient

Some people exchange pleasantries and personal stories over email before getting down to business. Other people read the subject line and click delete (or reply—but only if you’re lucky). If you know the person you’re emailing—or anything about them—you can probably hazard a guess about whether they’re the type of person who responds better to more lead-up and personal info or a short, pointed request.

For example, if you’re asking your cousin Fred to send you his professional-caliber photos of last summer’s family reunion, you’ll probably start off slow:

Subject: Hi and photos

Hi Fred!

I still have fond memories of our visit on the beach last summer! How did your bike race go over Labor Day weekend? If it was anything like our ride around the lake, I’m sure you made it onto the podium.

I remember you took a lot of photos over the weekend, and I’d love to revisit those memories. Would you mind sending me a few of your favorites?

Thanks, and looking forward to our next reunion!

Lots of nice family touches. And a few compliments don’t hurt either.

On the flip side, if you’re writing to a professor who gets hundreds of emails a day, it can be a good idea to put your request in the first line, or even in the subject line. For example:

Subject: Letter of recommendation by 1/15?

Dear Professor Stone,

I’m applying for a fellowship in New York this summer. Given my work as your research assistant, would you be willing to write me a letter of recommendation? Here is a link with more information.

Bottom line: especially if you really need a response, try to envision your email recipient’s habits and plan your message accordingly.

Intent: Define Your Goal

What’s the goal of your email? How do you want the recipient to respond? It might be helpful to open an empty “compose” box and write the goal of your email. Sure, you’ll do lots of rewording to make sure the final message is tactful, polite, and effective. But keeping that main idea front and center while you’re drafting will help you make sure that your reader knows exactly what to do.

Be strategic with your subject

For most recipients, you’re not going to make your request or give your news in the subject line; it takes some working up to. Write a subject that doesn’t give away the bottom line but does give a sense of what’s coming. Here are some words and phrases you might use:

• Planning for
• Reply by
• Request for
• Action needed
• Decision needed
• Signature needed

In dire circumstances there’s always the big, scary, all-caps “URGENT,” but if you’re trying to be tactful, try to avoid that one unless all else fails.

Put your ask up front

Nothing says confidence like coming right out with the bottom line at the top.

For example:

Dear Boss,

I want to manage the company’s next big case.

It might seem scary to make your demand right at the beginning, but it shows confidence, responsibility, and willingness to tackle a problem head-on. Especially if you’re asking for responsibility or you’re writing someone who gets mountains of emails every day, a good way to get what you want is to say that you want it from the get-go.

It’s all about structure

The ingredients: a subject that gets the recipient’s attention, a friendly greeting, a direct statement of the purpose of the email, any necessary detail, and a friendly sign-off.

The recipe: short, direct sentences to get your point across and paragraphs with clear, informative topic sentences. If you have a complicated message that can’t be conveyed in five or so sentences, use lists. Bullet points or numbered lists have several advantages:

• They’re easy to read
• They help highlight key details
• They prevent your email from looking like a wall of text

See?

Message: Choose Your Words with Care

You have your audience and your intent: now you need to craft your message so that it’s best suited for the audience, effectively gets across your intent, and helps you achieve your email goals. After you’ve written a polite, carefully worded email, take another look at your messaging. Especially if you’re asking for something or broaching a topic that the recipient might not be thrilled about, the importance of careful communication can’t be overstated.

Check your tone for anger, accusation, or sass

What you wrote might sound neutral to you, but words can come across as condescending or aggressive without a face and tone of voice to go along with them. If you’re sure email is the right way to communicate, make sure the email you write communicates the point in the right way.

Take this message, for example. In person, the words could be stated in a nice way, but in writing, they could come across as passive aggressive, bossy, or even rude.

Dear Kevin,

I wanted to check whether you’re going to finish your part of the group project in time. It’s due on Thursday, and your part is the last one we’re waiting for. Can you let me know if you’re going to finish your slides so we can wrap up the presentation?

Thanks, Brenda

Kevin may not be a great worker, but Brenda’s message might make him feel defensive or insulted. It might even backfire, making him not want to continue with the project. Brenda will have better luck with a message like this:

Dear Kevin,

I hope things are going well with you. Just checking in about your status on the group project to make sure we’re on the same page. As we agreed last week, you’re in charge of slides 4-6, and the presentation is due Thursday. Let me know if you want to go over anything in advance.

Thanks for your work on the project, and let me know if you have questions! Brenda

In general, if you’re saying something the recipient won’t want to hear, take these tips from Psych Central:

• Put yourself in the recipient’s shoes and write with empathy
• Avoid the word “should” or making the recipient feel guilty
• Don’t make threats or ultimatums
• It’s okay to offer advice, but don’t give it unless you’re asked

It’s all about treating the recipient like a human. And there’s more where that came from.

Add a human touch

If you’re writing something that could come across as accusatory or angry, or if you’re giving bad news, a few simple phrases can really help turn the tone around.

Here’s how Brenda softened what might have seemed like an accusation to Kevin:

• I hope things are going well with you (human touch)
• Just checking in (gentle nudge)
• Making sure we’re on the same page (giving the benefit of the doubt)
• Thank you for your hard work (acknowledging Kevin’s work so far—and making him feel like he’d better live up to the compliment)
• Let me know if you have questions (offering help)

Phrases like these can help soften a blow. And even if there’s not a blow, they can show a glimmer of humanity that makes any email a bit more pleasant to read and respond to.

Finally, remember your grammar

We couldn’t leave that one off the list. And not just because we kind of like grammar, but because writing full sentences with proper spelling and punctuation is an important part of communicating your point. Not only will writing properly ensure that you’re being clear, it will also make sure you look professional, self-assured, and thoughtful.

And those are very good adjectives on the path to getting what you want.

How to Write Dates Correctly in English

If writing dates has you stymied at times, it is probably for one of two reasons. The first is that date formats vary the world over, and we come across these different styles frequently in our reading. The second may be that you aren’t quite sure how to write dates with commas.

The key to overcoming your struggle with dates is to understand the prevailing conventions and then apply them clearly—and consistently.

How to Write the Year

Years should be expressed as numerals except at the beginning of a sentence. Most style guides agree that beginning a sentence with a numeral is poor style, so years placed at the beginning of a sentence should be written out as words. American writers tend not to use and after thousand when expressing a year after 2000 in words, but it is common in British English. Both are correct.

The year 1929 brought the Great Depression, the St. Valentine’s Day Massacre, and an influenza epidemic.

Nineteen twenty-nine brought the Great Depression, the St. Valentine’s Day Massacre, and an influenza epidemic.

Much happened in the political arena in 2016.

Two thousand and sixteen was an eventful year in politics.

Two thousand sixteen was an eventful year in politics.

How to Write the Month and Day

When referring to a specific date in the month-day date format, use cardinal numbers (one, two, three) rather than ordinal numbers (first, second, third). This may feel counterintuitive because we normally use ordinal numbers when we “speak” of dates. For example, one would say January first two thousand seventeen but write January 1, 2017.

Daniel was born on May 13.

Many people get confused about how to write dates with commas, so here is a rule of thumb: in the month-day-year format (used in the United States), place commas after the day and year. In the day-month-year format (used in the UK and other countries), do not use commas at all.

On May 13th, 2007 Daniel was born.

On May 13, 2007, Daniel was born.

On 13 May, 2007, Daniel was born.

On 13 May 2007 Daniel was born.

If you use a construction using of, it is fine to use an ordinal number. It is also fine to use an ordinal number when referring to a specific day without reference to the month.

Daniel was born on the 13th of May.

Daniel was born on the thirteenth.

How to Write Dates with Days of the Week

When writing a long-form date, use a comma after days of the week to ensure readability.

How fortunate that the world did not end on Friday, December 21, 2012!

Monday, May 5, is my last day of work.

How to Write Centuries

Here’s a tip: When writing about whole centuries, do not use an apostrophe before s. Centuries are plurals, not possessives.

For example, when we write the 1800s, we are referring to all the years from 1800 to 1899. Within that range are one hundred discrete years; that is, more than one: a plural. We can also refer to those years collectively as the nineteenth century in all lowercase letters.

Women often wore bonnets in the 1800’s.

Women often wore bonnets in the 1800s.

Women often wore bonnets in the eighteen hundreds.

Women often wore bonnets in the Nineteenth Century.

Women often wore bonnets in the nineteenth century.

How to Write Decades

Here’s a tip: Decades should be written as two-digit numbers with an apostrophe before them and an s after them (e.g., ’90s). When in doubt, write it out. You can write the entire decade in numerals with an safter it (e.g., 1990s), or write out the words (e.g., the nineties).

This is the way to think about writing decades using numbers: they are both abbreviations and plurals. A shorter way of saying “My mother was born in the 1940s” is “My mother was born in the ’40s.” The apostrophe (not an opening single quotation mark) indicates where the two century digits would be, had they been included. There is no need to put an apostrophe between the zero and the s—that would incorrectly indicate a possessive.

In the 80’s, I had a haircut like the lead singer of A Flock of Seagulls.

In the ’80s, I had a haircut like the lead singer of A Flock of Seagulls.

In the eighties, I had a haircut like the lead singer of A Flock of Seagulls.

Writing Dates as Numerals

All-numeral date styles should not be used in formal writing, but there may be times when it is appropriate to use them. When you do, be aware that not all countries express dates with numerals in the same way. American usage calls for a month/day/year date format, the United Kingdom and much of Europe use a day/month/year format, and most countries in Asia use the year/month/day format. Some countries use a combination of these depending on context (Canada, for example, uses all three, depending on who is the recipient of the communication).

So remember, if you are American and you write to your British friend inviting him to celebrate Independence Day on 7/4 with you, you can expect your guest to arrive on April 7 (which he will express as 7 April). Likewise, if he invites you to his Guy Fawkes Day party on 5/11, you will need to mark your calendar for November 5 rather than May 11.

Here’s a tip: Consider your audience when choosing how to express the date.

Correcting People’s Grammar: Just Don’t Do It

As grammar nerds, we care a lot about correct grammar, spelling, and punctuation. If you’re a grammar lover, maybe you’ve found yourself fighting the urge to correct a misspelled menu item at a restaurant. Perhaps you’ve even corrected a “who” to a “whom” when your friend used the wrong word in a story.

When it comes to grammar correction and education, where is the line between agitating and helping? As grammar lovers, our intentions are often good. We care about language and communication, and we want to make sure people are understood clearly. However, grammar lovers too often overstep the boundaries of appropriate correction.

Here’s a tip: Whenever you feel the urge to correct someone’s grammar, take a step back and ask yourself: does this person want to be corrected? If the answer is no, or even just maybe, keep your knowledge to yourself. Sometimes it’s hard, especially if an error is repeated over and over again. But remember that an essential part of good communication is building good relationships, and correcting people’s grammar without asking often hurts relationships rather than helping them.

Instead of correcting others’ grammar, try modeling good grammar in your own spoken and written communication. If people see and hear that you know how to construct a sentence correctly, they might reach out to you with questions about their grammar, spelling, and punctuation. These are your opportunities for education, not the moments when people make mistakes.

Above all, remember that communication—correctly formatted or not—is all about understanding. Give a little grace when it comes to grammar mistakes, and you’ll find that your communication improves overall.

Good vs. Well–How Should I Use Them?

A common English error is to misuse the words good and well. The rule of thumb is that good is an adjective and well is an adverb. Good modifies a noun; something can be or seem good. Well modifies a verb; an action can be done well. However, when you’re talking about health, well can be used as an adjective.

All you need to remember when you are pondering whether good or well is best for your sentence is that good modifies a person, place, or thing, whereas well modifies an action. If you’re having a good day, then your day is going well.

Did you do good on your exams?

Did you do well on your exams?

I can’t believe it! I did good on the test.

I can’t believe it! I did well on the test.

Here, we have a clear action verb: to do. Do should be modified with well, not good.

This is well lasagna!

This is good lasagna!

Lasagna is a noun—a thing—that should be modified with good. Nonaction verbs, like to be, to look, to seem, and to feel can also take good, the adjectival form.

Today, at last, life is good .

An Exception to the Well/Good Rule: Health and Wellbeing

When we refer to a person’s health or wellbeing, well is customarily used as an adjective.

She asked about David’s illness, and I told her he is good now.

She asked about David’s illness, and I told her he is well now.

When you tell someone “Be good!” you are talking about the behavior of that person. However, to say, “Be well!” is to express a wish for their good health.

Restrictive and Nonrestrictive Clauses—What’s the Difference?

A restrictive clause modifies the noun that precedes it in an essential way. Restrictive clauses limit or identify such nouns and cannot be removed from a sentence without changing the sentence’s meaning. A nonrestrictive clause, on the other hand, describes a noun in a nonessential way.

The terminology in this area of grammar can be confusing, so let’s get that out of the way. Because restrictive clauses provide key, identifying information, they are often referred to as essential clauses, and nonrestrictive clauses are also called nonessential clauses for the opposite reason. They are both types of relative clauses because the information they provide relates to the subject of another clause.

As if that weren’t enough, both function as adjective clauses, because they describe their noun antecedents.

Aren’t you glad we cleared that up?

Restrictive Clauses Narrow Things Down

Restrictive clauses are usually introduced by the relative pronouns that, who, whom, or whose. A restrictive clause can have an identifying function.

The astronaut who first stepped on the moon was Neil Armstrong.

The restrictive clause in this sentence is who first stepped on the moon. If we stripped it from the sentence, we would be left with this:

The astronaut was Neil Armstrong.

There is nothing grammatically wrong with this Spartan sentence. However, it does not have the same intent as the former example, which was to identify the person who first set foot on the moon’s surface.

A restrictive clause can also have a limiting function.

Children who eat vegetables are likely to be healthy.

If the restrictive clause who eat vegetables were removed from this sentence, the intended limits on the noun children would be no more.

Children are likely to be healthy.

Obviously, our intention with the first sentence was to point out which children, from among the world’s multitudes, perform a behavior likely to sustain their health. Thus, who eat vegetables is an essential element of that sentence.

Nonrestrictive Clauses Give Bonus Info

Nonrestrictive clauses provide additional but optional descriptions that can be excised from a sentence without altering its meaning or structure.

Kaylee, who just graduated from high school, is an accomplished figure skater.

While the nonrestrictive clause who just graduated from high school offers a good description of the subject of this sentence, Kaylee, the sentence retains its meaning without it.

Kaylee is an accomplished figure skater.

Commas and Relative Clauses

A broad rule you can apply to relative clauses in order to punctuate them correctly is that restrictive clauses are never offset by commas, whereas nonrestrictive clauses are. One way to remember this is that nonrestrictive clauses are removable, and commas mark the removable part of the sentence. Restrictive clauses, on the other hand, are essential; they need to blend with their sentences seamlessly, without commas.

Would you lend me the book, that you recommended last week?

Would you lend me the book that you recommended last week?

Oliver Twist which was Dickens’s second novel is a classic.

Oliver Twist, which was Dickens’s second novel, is a classic.

Deciding between That and Which

Confusion about when to use that and which has arisen for good reason: British and American English have different rules for them. In American English, that is used to introduce restrictive clauses, and which introduces nonrestrictive clauses.

The lamp, which was given to me by Aunt Betsy, is on the bedside table.

The lamp that Aunt Betsy gave me is on the bedside table.

In British English, it is often acceptable to substitute which in restrictive clauses.

The lamp which Aunt Betsy gave me is on the bedside table.

Of course, that could also be used acceptably in British English, which makes it safer, by default, to follow the American rule when in doubt. It also makes it easier to decide whether to insert commas, because if you follow the American rules, you can remember that commas should not precede that, but they should precede which.

A third option for the last example would be to rewrite it to omit all relative pronouns. If you can do that successfully, the clause is definitely restrictive.

The lamp Aunt Betsy gave me is on the bedside table.

Now that you have taken the time to learn these important rules, one thing has no restrictions at all: the limits of your writing.