Kyle A. Massa
ProWritingAid Marketing and Support Specialist
Published Feb 25, 2019


The apostrophe is just a little squiggle. But it’s a powerful little squiggle. In today’s post, we’re going to give the apostrophe the spotlight it deserves. Here are some thoughts on when to use it, when not to, and why it's so awesome.


  1. A Brief History of the Apostrophe
  2. Ways to Use the Apostrophe
  3. Celebrate the Apostrophe!

A Brief History of the Apostrophe

Apostrophes first entered the English language via French and Italian somewhere around the 16th century. The apostrophe was mostly used as a substitute for other letters. Take, for example, this quote from William Shakespeare's Henry V:

“In cases of defense ‘tis best to weigh the enemy more mighty than he seems.”

Here we see our apostrophe replacing the “I” in “it.” That rule still applies to apostrophes today, though it’s not used as often as it once was. Anyway, that little squiggle saw more and more work throughout the intervening years, and still does to this day.

Ways to Use the Apostrophe

Apostrophes still stand in for letters today (though you won’t hear anyone saying “‘tis” anytime soon). The most common use is within contractions.


A contraction is a combination of one or more words using an apostrophe. You know them.

  • Would not --> Wouldn’t
  • Cannot --> Can’t
  • Should have --> Should’ve

We use contractions in speech every day. In writing, their usage is less cut and dried. For example, if you’re writing a research paper or thesis, you might consider avoiding contractions so as to appear more formal. However, if you’re writing a blog post, you’d probably prefer to use contractions (and therefore our friend the apostrophe).

For example, compare these two sentences:

With contractions: We probably shouldn’t have watched so much Netflix—and we wouldn’t have! But once the next episode started, we couldn’t turn it off.

Without contractions: We probably should not have watched so much Netflix—and we would not have! But once the next episode started, we could not turn it off.

If you’re striving for a conversational tone in your writing, contractions are vital. That second example sounds like a robot! Use apostrophes to make contractions where necessary.

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Possessive Case

Apostrophes are also one of the key ingredients of possessive case. Just take a noun and slap an apostrophe plus “s” on the end, like this:

  • Nancy’s husband is named Malik.
  • The quarterback’s biggest mistake was throwing into triple coverage.
  • Daenerys’s most fearsome dragon is Drogon.

Notice that last one ends with an “s,” yet also has an apostrophe and another “s.” This is a common point of confusion. When writing the possessive form of a proper noun ending in “s,” use the second “s” as well, as we’ve done for the Mother of Dragons.

The classic mistake of contractions and possessives is the possessive form of “it.” It's not “it's.” “It’s” is a contraction of “it is.” If we want to express possession using the pronoun “it,” the proper word is “its.” Some examples:

  • The Departed is a great film, but most agree its biggest flaw is its bloated runtime.
  • The ship can’t hold its cargo for much longer.
  • It’s weird to see its influence after so many years.

Writers also sometimes confuse “you’re” and “your” in a similar fashion. The former is a contraction of “you are” and not the possessive form of “you,” even though it has an apostrophe. The latter is the correct possessive form.

  • Your birthday is coming up, right?
  • Look, I didn’t mean to step on your toes back there.
  • You’re not going to believe what your son did today.

In fact, the apostrophe is unnecessary when dealing with most possessive pronouns:

  • Hers is the better claim.
  • His reflexes are impeccable.
  • That one's theirs, this one's ours.

Just when we think we have a usage rule memorized, we find confusing exceptions like these. Thanks a lot, English!

Plural Possessive Case

Apostrophes play a slightly different role when indicating plural possessives. In those instances, just add an apostrophe to the end of the word without the additional s. Here are some examples:

  • Our writers’ group meets every Wednesday night.
  • Voters’ opinions are split on the latest issue.
  • The Players’ Union isn’t going to like this…

Remember: Almost all plural possessives end with an “s” already, so there’s no need to add another.

Celebrate the Apostrophe!

Now that you’ve finished your crash course, go use that powerful little squiggle.

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Kyle A. Massa
ProWritingAid Marketing and Support Specialist

Kyle A. Massa is a speculative fiction author living in upstate New York with his wife and their two cats. He loves the present tense and multiple POV characters. When he grows up, he wants to be a professional Magic: The Gathering player. Visit his website at or download his debut novel, Gerald Barkley Rocks, for Amazon Kindle today.

Great post on the little yet powerful apostrophe. Prowritingaid is a great tool for writers.

By Greg Wulff on 01 March 2019, 01:54 AM