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Apostrophe Trouble

Which to Use: Its or It’s? Whose or Who’s? Your or You’re? There, Their or They’re?

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These homophones (sound-alikes) pose vexing questions for many writers: even if we know the difference (but maybe can’t explain it), we often make typographical errors and insert one when we mean the other.

The Difference: Possessive Pronouns versus Contractions

Possessive pronouns modify nouns and indicate possession of those nouns.

  • Whose car is that? The car belongs to Gary.

Contractions are a written manifestation of spoken language, in which letters are omitted to facilitate pronunciation; the missing letters are replaced with an apostrophe.

  • Who’s the owner of that car? = Who is the owner (an apostrophe replaces the “i” in “is”)

Examples to Learn from: Possessive Pronouns versus Contractions

Its vs. It’s

  • The cat hurt its paw. (the paw of the cat: possessive )
  • It’s the cat purring. (it is: contraction)

Whose vs. Who’s

  • Whose car is that? (to whom does it belong: possessive)
  • Who’s the owner of this car? (who is: contraction)

Your vs. You’re

  • Is that your cat? (to whom does it belong? possessive)
  • You’re the owner of that cat? (who is: contraction)

There vs. Their vs. They’re

The distinction between these three is a little more complicated.

  1. “There” indicates place or location: Put the box over there.
  2. “Their” is a possessive pronoun that indicates possession: Put their box in a separate place.
  3. “They’re” is a contraction for “they are”: They’re in the kitchen.
  • They’re (contraction) putting their (possessive) boxes over there (location).

Application Strategies

Strategy 1: When in Doubt, Rephrase!

Not sure whether you need a possessive pronoun or a contraction with an apostrophe?

  1. Ask yourself if the word in question can be rephrased as a possessive phrase, “of the [blank],” or a being phrase, “[blank] is”;
  2. “of the [blank],” no apostrophe; “[blank] is,” apostrophe required

Strategy 2: Proofread with a Focus on These Words

When you proofread, take time to proofread any piece of writing one time through solely for instances of such words.

To streamline your proofreading, consider using your word processor’s “Find” tool to search your document for each of the terms discussed in this guide, taking time to evaluate each use: its, it’s, whose, who’s, your, you’re, there, their, and they’re.

Last revised: 07/2008 | Adapted for web delivery: 07/2021

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