Basics of writingPunctuation

Punctuation basics: apostrophes

From Scott and Rick:

The apostrophe is another punctuation sticking point for many writers. When to use it, when not to use it, and where to use it: all of these can present difficulties. Just keep a few simple rules in mind, and most of these situations will seem self-explanatory. All of these guidelines, and some of the examples, come from the Chicago Manual of Style (CMS).

[NOTE FROM RICK: This was originally Scott’s post, but I’m chiming in to make some additions and a couple of corrections (that were not Scott’s fault). Scott has the 15th edition of the CMS, while I have the newer 16th edition (because I sent Scott my old one when I got the new one). The 16th made a couple of changes that affect some of the rules Scott put into his original post.]

The apostrophe has two purposes. The first is to show possession.

Example: John’s book, the car’s shape, the house’s color. The second is to indicate the omission of a letter as in a contraction.

Examples: don’t (for do not), haven’t (for have not), they’re (for they are).

A conflict between these two uses of the apostrophe is what causes so many people problems with where people run into trouble with the homophonic pair: “its” and “it’s” How do you tell them apart?

Before we get to that, let’s brush up on possessive pronouns. Pronouns show possession in one of two ways. As adjectives (modifying nouns) they show to whom something belongs. The possessive adjectives: my, your, his, her, its, our, their. The corresponding possessive pronouns: mine, yours, his, hers, its, ours, theirs. Most of the latter end in “s.” POSSESSIVE PRONOUNS NEVER TAKE AN APOSTROPHE. This is one way to help you remember which to use.

“It’s” is a contraction if “it is”. You can’t have a contraction without an apostrophe.

But a surefire test is to substitute “it is.” If “it is” makes sense in the sentence, you’ve gotten it right because you’re using the contraction correctly.


It’s going to be a beautiful day. (It is going to be a beautiful day.) MAKES SENSE.

I don’t know if it’s better to buy or lease a car. (I don’t know if it is better to buy or lease a car.) MAKES SENSE.

After being out in the rain, the cat had it’s fur all plastered down. (After being out in the rain, the cat had it is fur all plastered down.) DOESN’T MAKE SENSE, SO “its fur” WOULD THE CORRECT FORM.

And here’s an exercise for you. In the following sentence, decide which form is correct by substituting “it is” in each case. Try it before peeking at the answer at the end of the blog.

Whenever I look for a new book to buy, all I have to do is read its first page because I find its easy for me to tell if its something I’m going to like by how its author wrote its first few lines.

Another error writers make is to use an apostrophe to make a word plural. The rule: This is NEVER! correct. Okay, every rule in English has an exception. Or more than one exception.

Before the CMS 16th edition, the rule was that a phrase in quotes could be made plural with an apostrophe: “Happily ever after’s”, with the apostrophe-S inside the quotes, not out. But the CMS 16th ed. changed this. The NEW CMS RULE is that you do NOT use an apostrophe to make words in quotes plural.

I love “happily ever afters” in books.

How many more “To be continueds” can we expect in that TV series?

The CMS also suggests that when the wording is awkward, one should reword. Thus:

I love books that end with “happily ever after.”

How many more times can we expect to see “To be continued” in that TV series?

Hyphenated words made plural can also be tricky. The rule here is twofold: first, check Webster’s to see how that reference writes the plural. Barring that, use common sense. Examples: brother-in-law becomes brothers-in-law, and hole-in-one becomes holes-in-one. No apostrophes!

If you take a word that is not normally a noun and use it as a noun, it USED TO BE widely accepted to use the apostrophe for the plural form. Example: maybe’s. But, again, this was changed in the newer CMS. Here are some examples of more common cases for plurals.

ifs and buts
dos and don’ts
threes and fours
yeses and nos

And finally, single LOWERCASE letters (e.g. x’s, a’s, i’s) use the apostrophe to avoid confusion with words “is” and “as.” But in general, UPPERCASE letters do not use the apostrophe (the three Rs) as long as there is no confusion. “He received all As and Bs on his report card.”

Abbreviations with more than one period (M.D. becomes M.D.’s) can be made plural with the apostrophe. But for the most part, using the apostrophe for this purpose is taboo. Nothing screams “amateur writer” like words made plural with the apostrophe. NOTE: In the latest CMS, college degrees now generally omit the periods: BS, MS, PhD

Other examples that do NOT use the apostrophe to make them plural:

the 1990s
eds. (as an abbreviation for “editors”)

The apostrophe is never used to form the plural of a family name:

the Jeffersons (not the Jefferson’s)
the Joneses (not the Jones’s)
“every Tom, Dick, and Harry” becomes “all the Toms, Dicks, and Harrys”

These are by no means all of the cases. We pointed out a number of the exceptions to show you how many there are. Unfortunately. The good news is that you probably won’t run into many of these in most fiction writing, but always check your dictionary! Even if you’re pretty sure.

A number of words have unexpected plurals (especially some foreign ones used in English), such as the familiar words radius, radii. We can’t stress enough how valuable the CMS is for writers. It’s well worth the investment because it can make the difference between good sales and poor sales (due to bad reviews for bad grammar).


On to the possessive forms. Most writers will get the simple possessive forms correct. We all know that a singular word (not ending in the letter “s”) only needs to add an apostrophe and an “s” to become possessive. Examples: the dog’s bowl; the car’s engine. If the word is plural, and ends with an “s,” add an apostrophe to the end to make it possessive. Examples: cars becomes cars’. Thus we have “the dogs’ bowls” and “the cars’ engines” when referring to multiple dogs having bowls, etc.

Some words in the English language already end in “s” but are still in their singular form. Although it may look awkward, stick with the above rule. Example: bass becomes bass’s (as in the fish, not the musical instrument).

The CMS points out a few interesting examples that might cause a bit of doubt. What if you have a company name that ends in a punctuation mark, such as Yahoo!, and you need to make it possessive? The simple answer is to stick to the rules. Yahoo! becomes Yahoo!’s.

What if the word, while plural, refers to a singular entity, such as “The United States”? Even though there is only one country named “United States,” the word “states” is plural, and therefore the possessive is written United States’.

What about names that end in “s” with an “eez” sound, such as the Ganges River? Obviously, you could write it as the “Ganges River’s waters.” But if you wrote it without the word “river,” the apostrophe goes at the end: Ganges’ waters. Otherwise, you’d say it as “Gangeses,” which would sound awkward.

[NOTE: For a long time the Xerox corporation used the possessive form of Xerox’. Recently, they went back to the more standard rule of ‘s, so it’s now–officially–Xerox’s.]

For those who are wondering, the correct spelling of the familiar exclamation phrase is “for goodness’ sake.” And for those whose writing requires coarser language employing the f-word, be sure you get it right “for fuck’s sake.”

A few more: children’s literature; the horse’s mouth; puppies’ paws; the women’s restroom; the people’s choice.

In the latter case, if you’re referring to several distinct groups of people, such as the various racial groups that populated a location during its history, the correct possessive there would be peoples’ as in “the peoples’ legacy to the country’s history.”

When using multiple terms together in the possessive form, many people get crossed up, even in their speech. How would you make “brother and sister” into a possessive form? The last term receives the apostrophe: my brother and sister’s car. I’ve heard this spoken all different ways, but usually people apply the possessive form to all the nouns involved (brother’s and sister’s car), which is incorrect.

[NOTE: A difference in meaning exists between “my aunt and uncle’s house” and “my aunt’s and uncle’s medical records.” In the first case, we’re referring to ONE house, belonging to the aunt and uncle. In the second case, we’re talking about two different medical records, one for the aunt, and one for the uncle, not a combined one. “My brother and sister’s dogs” refers to multiple dogs owned jointly by your brother and sister, as opposed to “my brother’s and sister’s dogs,” which refers to your brother and sister each having multiple dogs of their own. Confusing? Yeah.]

Many times, a name will end in the letter “s,” but the “s” is not pronounced. In this situation, the word is made plural by adding only an apostrophe. Examples from the CMS: the marquis’ mother and Descartes’ three dreams. But if the “s” is pronounced, the full apostrophe “s” must be used. In my (Scott’s) science fiction vampire novel, 14 Days ‘Til Dawn, I encountered this with a character named Sarus. Since the “s” is pronounced, the possessive form would be Sarus’s, and would be pronounced “sair-us-iz.” If, in my mind, Sarus pronounced his name with the “s” at the end silent, it would be written “Sarus'” in the possessive, and pronounced something akin to “Sarah’s.” In this case, since I invented the name, I get to decide how it is pronounced, which indicates the rule to follow.

[A RICK NOTE: In Scott’s case, Sarus’ is also correct because, as an editor once pointed out to me, we would still pronounce it “Saruses.” It’s a bit cleaner without the extra “s,” but this is also a case where it’s up to the writer to decide which spelling he prefers. The CMS now recommends leaving the extra “s” in for consistency as with the standard rule for forming possessives, but both ways are considered acceptable.]

The use of possessives versus the attributive form is a gray area. The attributive form refers to a noun used as an adjective, and is not clearly used as a possessive. Examples would be employees’ lounge and homeowners’ associations. The CMS indicates that while some people will drop the apostrophes in these cases, the preferred method is to only do so in the case of proper nouns. Examples: Publishers Weekly and Department of Veterans Affairs.

If a noun is followed by a gerund, the noun may be changed into the possessive form. Example: Steve’s running of the show was shoddy. In that case, the possessive is clearly the right choice. However, there are situations where, although the possessive would not be incorrect, it might sound a bit awkward.

Example: Steve anticipated his daughter’s arriving that evening.

This would sound better if reworded to remove the gerund Steve anticipated his daughter’s arrival that evening.

[A RICK NOTE: A gerund is an -ing verb form used as a noun: swimming, flying, running, breathing]

Or, if the context has already implied that the reference is to Steve’s daughter, a pronoun in the possessive form would make this even smoother: Steve anticipated her arrival that evening. Much better. This last example brings up a good rule of thumb. If the possessing noun that comes before the gerund cannot be replaced by a possessive pronoun without sounding ridiculous, then do not use the apostrophe. For example, which is the correct choice here? I watched Bob painting a picture. OR I watched Bob’s painting a picture. Apply this rule of pronoun substitution. I watched his painting a picture. This sentence makes no sense, so the apostrophe (Bob’s) is left out.

If the word “of” is included in the possessive phrase (to indicate a noun is one of several), the standard possessive form is still used. Example: A daughter of Pete’s. This implies that Pete has more than one daughter, but we are referring to just one of them. Another way to write this would be, One of Pete’s daughters, but either would be acceptable.

If a term is written in italics, the possessive apostrophe and “s” should not be inside the italics.

Examples: Star Trek‘s fans. The Chicago Manual of Style‘s readers.

However, in the case of a noun (such as the title of a poem or a piece of music that is in quotation marks, it should not be made possessive, ever.

Example: Lovers of “Ode On A Grecian Urn” is correct, not “Ode On A Grecian Urn’s” lovers.

But, as we noted above, fiction writers likely won’t encounter these very often.

The rules laid out here cover most situations you’ll encounter in your daily use of apostrophes. When in doubt, refer back to this blog post or check the CMS. Chances are that a rule for your dilemma has already been written, so all you need to do is find and follow it.

NOTE: The CMS can be accessed online for a subscription fee, but if you Google your question and put “Chicago Manual” in the Google search words, you’ll be able to find the answer without subscribing. For example, do a Google search on “gerund possessive chicago manual” and you’ll find a list of topics you can click on. Also, even if you own the CMS, you’ll still find additional answers and examples online that the book doesn’t cover specifically because things do change, and the CMS board is always adding new information and clarifications.

We know this blog post gave you a LOT to absorb, and we hope it helps. Even if you don’t remember it all, we hope it has made you aware of some things to watch out for.

For next week we have a guest author interview that we think you’ll enjoy.


[CORRECT ANSWER TO THE “ITS/IT’S” EXERCISE: Whenever I look for a new book to buy, all I have to do is read its first page because I find it’s easy for me to tell if it’s something I’m going to like by how its author wrote its first few lines.]


–Scott & Rick

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