Blog Grammar Rules 7 Grammar Rules the Best Writers Break

7 Grammar Rules the Best Writers Break

The ProWritingAid Team

The ProWritingAid Team

ProWritingAid: A grammar guru, style editor, and writing mentor in one package.

Published Jun 18, 2018


In life, writers must obey a single rule: write for your audience. If you’re writing fiction, your dialogue must be natural. So you write in conversational English, which is less than grammatical at times. And if you’re writing for academia or other stuffy audiences, your prose must be formal.

If you’ve learned the many rules of English usage and are adept at wielding them properly, feel free to break the following rules now and then.

  1. 1. Split infinitives
  2. 2. Starting sentences with conjunctions
  3. 3. Ending sentences with prepositions
  4. 4. Avoid contractions
  5. 5. Dangling modifiers
  6. 6. Who vs. whom
  7. 7. Less vs. fewer
  8. Final thoughts

1. Split infinitives

The ban on splitting infinitives is dying a slow death, which makes me happy. Certain infinitives need split to sound better. Going out of your way to not split infinitives sometimes causes confusion. Let’s look at an example:

  • Split: Splitting your infinitives allows you to more effectively clarify your thoughts.

  • Unsplit: Splitting your infinitives allows you to clarify more effectively your thoughts.

Doesn’t the first one sound better to your ears? And there’s the infamous Star Trek reference that perfectly summarizes why break this rule:

  • Split: To boldly go where no man has gone before.

  • Unsplit: To go boldly where no man has gone before.

Seriously. This is one rule that needs to fall by the wayside.

2. Starting sentences with conjunctions

And another rule that needs abolished is not starting sentences with conjunctions. Some sentences flow better conversationally when started with conjunctions.

Again, it comes down to your readers.

If you’re writing for an academic journal, chances are you shouldn’t break this rule. If you’re writing a blog post for your website, have at it.

  • Some rules are there for good reason, especially those ensuring your safety. And some rules are meant to be broken.

3. Ending sentences with prepositions

Winston Churchill refused to write, "This is pedantry up with which I will not put" to avoid ending his sentence with a preposition. So if Churchill found it silly, the rest of us will find times to break the rule.

Particularly when using "up" or "to," it’s hard not to leave them stranded at the end of a sentence.

  • What is he up to?

  • Are you going up?

  • What are you looking at?

  • This is one broken rule you can get away with.

4. Avoid contractions

Today’s writing style, especially for the internet, is casual conversational. You may find it hard to use contractions at first because your grammar teachers pounded this rule into your psyche with years of red pen abuse. But today’s more relaxed writing style accepts contractions freely.

Again, it comes down to your audience. Some industries and professions are more formal than others. You may have a client who insists you avoid contractions, always use the Oxford Comma, and more. But if you’re writing blog posts for the masses, contractions make your work more easily read.

5. Dangling modifiers

Some sentence constructions sound better when your modifiers are dangling out in front. Here are a few examples:

  • To clean up the hazardous mess, the area was cordoned off.

In this example, the modifier refers to an unnamed subject. But the sentence works if you’re trying to avoid naming the subject.

  • Arriving at the restaurant, it was nice to see our whole party already there.

You could rewrite this sentence with the pronoun "I" or "We" if you felt so inclined.

  • Arriving at the restaurant, we were happy to see our whole party already there.

6. Who vs. whom

Must we all sound like stuffy English butlers? Can’t we ditch "whom" once and for all?

If you don’t want to sound affected or pompous, you can avoid using "whom." Most people don’t understand the rules of when to use "whom" anyway and will find your prose sounding funny if you use it.

Have you ever heard the saying, "It’s not what you know, it’s who you know," when referring to the power of networking? It should read:

  • It’s not what you know, it’s whom you know.

But most people would be afraid to say it in a conversation for fear of sounding pretentious.

7. Less vs. fewer

Part of our everyday lexicon in the United States is the phrase:

  • "Ten items or less"

If you follow grammar rules obediently, however, it should read:

  • "Ten items or fewer"

Consider how today’s English breaks the rule of "singular count noun" and "plural count noun." You wouldn’t say:

  • Teenagers who are fewer than 16 years old may not get a driver’s permit.

  • You must drive fewer than 60 miles per hour on this road.

  • Describe this building in 10 words or fewer.

Technically, in the above sentences, you should use "fewer" instead of "less." But how odd do they sound to those with a native ear for English usage?

We see no problem with:

  • Teenagers who are less than 16 years old may not get a driver’s permit.

  • You must drive less than 60 miles per hour on this road.

  • Describe this building in 10 words or less.

Final thoughts

These 7 rules are top on our list of pet peeves. Surely there are other rules great writers break! Let us know in the comments below what rules you routinely ignore.

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The ProWritingAid Team

The ProWritingAid Team

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For me, the tips are very useful. Thank you. I will try this as I write my memoir.
Another peeve: Insisting on "That's he" or "It is I" rather than the far more usual "That's him" or "It's me." Re the Star Trek example: Replacing "to boldly go" with "to go boldly" isn't just worse, it doesn't even convey the same meaning. The latter means to go in a bold manner, but the former implies that the very act of going is in itself bold. English has many phrasal verbs comprising a verb and one or two (and sometimes more) prepositions or adverbs, often conveying a meaning not obvious from the individual words, e.g., "to get up," "to watch out," "to put up with." Phrasal verbs often appear at the end of a clause, and it is perverse to dismember them in in superstitious avoidance of a terminal prepositions. Of course, the simplest way to modify a sentence to avoid a preposition at the end is to append a comma and vocative noun or phrase, such as ", you Bozo!" Complaining about initial conjunctions reflects a fundamental misunderstanding of their grammatical role. And anyway, classics of literature such as the King James Bible are full of them. Hence if someone objects to your using an initial conjunction, threaten to denounce them to the Inquisition. And if they persist, do it. Not many people get denounced nowadays and I bet the Inquisition will be delighted to hear from you. Obviously I agree with most of what you say, but to be contrary I'll note that the rule about "less" versus "fewer" actually has to do with whether something comes in discrete units. (The singular-plural distinction if a misleading rule of thumb.) Hence "fewer than 60 miles per hour" and "fewer than 16 years old" are wrong as well as weird, since miles and years are not countable items like raccoons but measures of continuous quantities.
I love your passion! Thank you so much for sharing this opinion - fascinating stuff!

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