How To Conquer The 10 Most Confusing Grammar Rules

March 4, 2024

The Most Confusing Grammar Rules

Do you feel like you have a pretty good grasp of the English language? Even if you do, there are probably some grammar rules that trip you up.

Don’t stress! I’m Kaitlin, an editor for indie fiction authors, and I still have trouble with some grammar rules!

This blog will explain ten of the most confusing grammar rules so you never have to waste time thinking about them again.

1. Who vs. Whom

Want to know a secret? No one cares about this one. 🙂

Whom has really fallen out of fashion, especially in fiction writing, so if you aren’t sure when to use it … don’t! Stick with who and you should be fine.

BUT if you really want to know a trick for correct usage, try this:

Replace the word (who/whom) with he or she. If it still works, who is the right one. If it works when replaced with him or her, use whom.

2. Ending Sentences with Prepositions

Grammar sticklers love to argue with people who do this.

But good news! This is a fake rule.

No, really. This “rule” was created by John Dryden (or Joshua Poole) because he wanted English to mirror Latin.

That’s it. That’s the reason. One guy three hundred years ago thought it would be cool and ever since we’ve had to listen to grammar experts tell us about it. Cool cool cool. I love rules that make no sense.

So, preposition away! And if anyone tries to correct you, direct them to this recent article by Merriam-Webster about the origin of the fake rule.

3. Fewer vs. Less

Grocery store express lanes, am I right?

Okay, but seriously, are you ready to be confused?

Use FEWER when you can count the things (words, items, troubles) and use LESS when you are talking about amount or quantity that is measured (less time).

If we were to go by that, then yeah, all grocery store express lane signage is wrong.

BUT WAIT.

Less can also be used for things that are counted.

(What? I know. I did tell you this was one of the most confusing grammar rules.)

Would it sound weird to have your teacher tell you to write an essay of 250 words or fewer? Yeah. That would be odd. 250 words or less sounds better.

This is one of those rules where there isn’t really a definitive answer. In fact, there’s some evidence that it was created by Robert Baker just because he preferred it.

Merriam-Webster says that “a definitive rule covering all possibilities is maybe impossible.”

So, just go with your heart, and don’t get fussy about the grocery store express lanes signage. It’s fine.

4. Lay vs. Lie

Lay needs an object.
Lie doesn’t need an object.
Seems simple, yes?
WELL GUESS WHAT. This is one of the most confusing grammar rules because of the tenses of the verbs.
It’s tricky because the past tense of the verb lie is LAY. So, a person CAN lay down … if they’re speaking in the past tense.
The past tense of the verb lay? LAID. Which really means that we shouldn’t say “He laid down” because it should be “he lay down” but even I think that looks odd.
Where does that leave us? Doing our best!

5. Apostrophes on Words Ending with S

This is one of the grammar rules in English that trips me up the most because so many people are taught to do this incorrectly (or not using The Chicago Manual of Style).

CMOS 7.17 says that, even if a word ends in s, you should still place the apostrophe and an s to show it is singular possessive.

Done correctly, this looks like:

Kansas’s legislature

Jesus’s teachings

Dickens’s novels

To show something is plural possessive, put the apostrophe after the s.

The Associated Press Stylebook says that the correct way to show singular possession is: Kansas’ or Jesus’. That looks weird to me! But the other way may look weird to you!

Different style guides say different things so the most important thing to remember is to be consistent with the style guide you have chosen to use. It’s a confusing grammar rule because it seems like each style guide handles it differently! As a fiction editor, I only work with The Chicago Manual of Style.

6. E.g. vs. i.e.

These are both Latin phrases that mean similar things.

E.g. means “for example.”

I.e. means “in other words.”

If you are listing examples, go with e.g.

If you are explaining something, go with i.e.

Or, hear me out, use neither of them and figure out some other way to say what you mean.

7. Oxford Comma

Ooh, as an editor, I gotta tell ya, I love the Oxford comma. Sometimes called the serial comma, this plays an important role in clarity.

When listing three or more things, the Oxford comma comes before “and” or “or” and the last item. This prevents weird sentence structure like this ACTUAL QUOTE from The Times:

“Highlights of his global tour include encounters with Nelson Mandela, an 800-year-old demigod and a dildo collector.”

See how the Oxford comma would have made that sentence a little clearer?

The Associated Press Style does not require its use. You may also notice the Oxford comma missing in advertising campaigns, as well as newspapers and magazines.

Since I edit fiction where the serial comma is the standard, I use it and place it in all the manuscripts I edit.

8. Starting a Sentence with a Conjunction

Okay folks, this is another fake rule. (Isn’t it odd how some of the most confusing grammar rules are just made up?)

Feel free to begin a sentence with a conjunction (but, and, so). CMOS 5.203 says it’s a fake rule (and no one can figure out who started it!).

I pronounce this rule … dumb. Conjunction your little heart out!

9. Comma Before a Conjunction

CMOS 6.22 says if two independent clauses are being connected with a conjunction you should use a comma. An easy way to spot this is to see if you can separate the sentence into two sentences at the conjunction. If both sentences make sense on their own (and you can be inferred), put the comma in.

Exception? If the phrases are short. This is kind of a judgment call. If you aren’t sure, ask your editor. 🙂

10. When to Hyphenate

I keep the CMOS hyphenation guide (7.89) bookmarked for a reason. This is one of the most confusing grammar rules!

There are too many hyphenation rules to go through here, but here are three of the most common I see as an editor:

Colors before / after a noun. Use the hyphen before the noun, but not after. For example: blood-red eyes vs. his eyes were blood red.
Adjectives + noun. Use the hyphen if it is before, but not if it is after. One of the examples CMOS has is: open-ended question vs. her question was open ended.
Ages. YES hyphen: four-year-old or thirty-nine-year-old. NO hyphen: ten years old or ten years of age.

Bonus fact: You really never use a hyphen with a pronoun. The closest you might come to doing this would be when using self (not a pronoun, but you get what I mean). Self-reliance or self-consciousness.

Do you have a handle on the most confusing grammar rules?

I hope this blog has helped you get a grasp on some of these English grammar rules! Many native speakers of English know WHAT sounds right, but don’t always know WHY something sounds right. If you’re sick of spending all your time scouring Grammarly or Google for answers, send me a message. I know all of this stuff so you don’t have to! 🙂

I’m Kaitlin, an editor for indie fiction authors, and I’d love to talk about your next project.