15 grammar rules it’s okay to break (Infographic)

Editor’s note: This article was reviewed and updated in July 2026 to meet Expert Editor’s latest editorial standards.

Rules were made to be broken – just ask James Dean.

But to be a grammar rebel, you have to understand the rules in the first place. How else do you know if you’re even breaking any?

The beauty of language is its fluidity. Language is always changing, evolving, and adapting to the needs of its users. Shakespeare’s English from the late sixteenth and early seventeenth centuries is most unlike how we write today, for instance.

And with the direction technology has taken us in the last 20 years, everyone with access to a computer or smartphone is now a writer. Everyone is having their writing read and everyone is making mistakes. So aim to make better mistakes.

Learn which rules are okay to break. It’s often better to be informal and communicate effectively than to follow the rules and alienate your audience with overly formal writing.

Go on… take a walk on the wild side. These are the rules and how to break ’em.

Every person who has had to learn English as a second language will tell you that for every grammar rule there is an exception.

Here are the 15 grammar rules you really should break once in a while:

Never end a sentence with a preposition

This is one from the ark and probably the most broken rule because of how formal sentences become when the rule is followed.

Break it because: you’re not writing a research paper, and asking someone, “From where do you come?” seems stilted and pretentious.

Know the difference between who and whom

Who refers to the subject of a sentence (the person doing the action), and whom refers to the object (the person on the receiving end of the action).

Break it because: you have no idea. If that’s the case, default to who because an incorrect whom is far more obvious. It’s also common for people to break this rule in colloquial speech and ask, “Who did you invite?” rather than say correctly, “Whom did you invite?”

Never begin a sentence with a conjunction

This old-timey rule still stands because conjunctions traditionally join clauses or other grammatical units, and a sentence-opening conjunction can look like a dangling connector without the clause it belongs to.

Break it because: the context is already established or you’re still going to include a subject, verb and object. E.g. “And that leads me to my next point…”

Never describe a single noun with a plural pronoun

It stands to reason that pronouns need to agree with the nouns that they substitute. E.g. “The boy ran to the playground and he jumped onto the swing.”

Break it because: It’s the 21st century, and some people prefer non gender-specific pronouns and plural pronouns are the alternative. Also, you might not know the gender of the person in question. E.g. “Somebody left their hat on the train.”

Don’t use sentence fragments

Sentence fragments are frowned upon because they’re missing a piece of the puzzle that makes up an independent clause: a subject, a verb and an object, and they rarely make sense on their own.

Break it because: With an established context, you don’t need to include each puzzle piece. E.g. “Would you like to go on a date with me?” “I’d love to!”

Don’t use double negatives

Ever heard that two negatives make a positive? Doubling your negatives will convey the opposite message to what’s intended.

Break it because: you intend to convey regional dialect, slang or to add extra emphasis. E.g. “I don’t want none of what you’re cooking.”

Use the correct verbal agreement for a collective noun

Collective nouns describe groups of things acting as a single entity (a swarm of bees, a team of people, etc.). As such, the verbal agreement is singular. E.g. “The team is going out to lunch.”

Break it because: some collective nouns have been used as plurals for so long that common usage sounds more right than following the rule.

Wrong: “None of us are invited to the wedding.”

Right (but sounds wrong): “None of us is invited to the wedding.”

Use fewer and less correctly

Fewer is an adjective used to quantify nouns that can be counted, whereas less is an adjective used to quantify intangible nouns that can’t be counted.
Eg. Fewer coins vs less money.

Break it only when: common usage allows for it. E.g. “10 items or less”

Use the correct personal pronoun

Me, myself and I all describe oneself, but can’t be used interchangeably. I is the subject of a sentence. Me is the object of a sentence, and myself is a reflexive pronoun used for when the subject and the object are the same. “She smiled at herself in the mirror.”

Break it because: you want to sound regional or slang. E.g. “Me and my mates are going out.”

Into is directional, in to is a verb phrase

A trick to distinguish between the preposition and verb phrase is to replace into/in to with *in order to*.

Break it only because: it’s a common mistake you’re unlikely to be called out on. “Breaking into the museum” is directional movement; “Breaking in (*in order to*) to steal the jewels” is an action.

Avoid vague pronouns

Pronouns are used to refer to nouns and are helpful when avoiding repetition in sentences.

Break it when: you are sure there can be no ambiguity based on context established in the previous sentence. E.g. “When Jess picked up her baby sister, she was so happy.” (Was it Jess or her sister that was made happy?)

Do not split infinitives

Infinitives are verbs in their most basic form, usually preceded by the word to. E.g. to drink, to laugh, to dance. This sneaky rule is one that’s been hotly contested for a long time and was never more than a stylistic preference — popularised in the 19th century rather than rooted in any deep grammatical authority.

Break it because: it sounds good and sometimes adverbs fit well between to + verb. E.g. “She tried to quickly think of an awesome sentence for this example but she decided to keep it meta.”

Use farther for physical distance and further for figurative distance

To make the distinction, remember to use farther when describing distance because it has the word far in it.

Break it because: farther is slowly becoming antiquated; further is more commonplace in both types of distance. E.g. “We had to run farther today to catch up with our teammates who were further along in their training schedule.”

Use that and which correctly

That and which are both relative pronouns that introduce clauses. The standard distinction is that that introduces a restrictive (defining) clause — one essential to the meaning of the sentence — while which introduces a nonrestrictive (non-defining) clause, typically set off by a comma.

Break it because: informal language won’t change the meaning too much if you use either word, as long as you communicate clearly. E.g. “Which kitten is your favourite?” “My favourite is the one that has a white-tipped tail.”

Always spell out numbers under 10

Style guides differ on this one. The AP Stylebook recommends spelling out numbers zero through nine and using numerals for 10 and above, while the Chicago Manual of Style spells out numbers all the way through one hundred. In practice, in the digital age, every character can feel precious.

Break it because: you’re writing an informal article or you just don’t have enough space to write out seven.