21 Grammar Rules That Confuse Everyone

Despite what your teacher may have told you, starting a sentence with “and” or “but” is acceptable according to most style guides. But it does look a bit informal.

While they are both relative pronouns, “which” should be used in non-defining clauses with a comma, as in, “My car, which is in the shop today, has a flat tire.”

“That,” on the other hand, should only be used in comma-free clauses that are essential to the meaning of the sentence, as in, “The car that had a flat tire is in the shop today.”

Reduplication is the repetition of a word in a phrase like bye-bye or no-no. Ablaut reduplication changes the interior vowels of one or more of the almost-identical words in a phrase, as in tick-tock or lovey-dovey. Though we’re not usually aware of it, there is an order that the emphasized vowels should be placed in. In cases where there are two words, the first vowel should be “i” and the second is either “a” or “o,” as in hip-hop or chit chat. If there are three words, the order of the vowels has to be “i, a, o” as in tic-tac-toe. (Try reversing the order and see how it sounds.)

If a parenthetical phrase is at the end of a sentence, the terminal punctuation mark must be placed outside of the parentheses (like this).

(However, if the parenthetical is a full sentence and not part of another sentence, the punctuation mark is included within the parentheses.)

Here’s one we follow instinctively without questioning why: In most cases when multiple adjectives are used, their order is as follows: opinion, size, age, shape, color, origin, material, purpose – and then the noun they modify. They’re your “nice big old misshapen brown Italian leather hiking boots.” Try it out of order and see how strange it sounds.

There are dozens if not hundreds of exceptions to this rule, including weird, sovereign, glacier, seize, height, science, heist, leisure, foreign, vein, eight, caffeine… We could go on and on.

“Less” is used for hypothetical quantities or singular mass nouns (less money, less time), while “fewer” is used for items you can actually quantify (fewer dollar bills, fewer hours). However, there are cases where “fewer” is technically correct but would sound jarring, so most authorities accept the use of “less” – like “25 words or less” in a contest or “10 items or less” at the supermarket.

For those learning English, there is a long list of irregular plurals to memorize including feet, women, teeth, deer, mice, children, lice, and oxen.

Although they can sometimes be used interchangeably, “may” and “might” have different connotations. “May” signifies when there is a possibility, or when something could be factual. “Might” implies that something is hypothetical or uncertain.

“Lay” needs an object, as in, “I’m going to lay this book on the table,” while “lie” doesn’t take an object, as in, “I’m going to lie down.” It gets very confusing in past tense however, as the past tense of “lie” is “lay,” as in, “He lay down early last night” – and the past tense of “lay” is “laid,” as in “I don’t remember where I laid the book.”

When talking about two people at the same time, the verb must agree with the compound subject. Sometimes it’s straightforward, as in “Max and Stan are walking the dog.” But if there is an “or” or “nor” in the subject, the verb will agree with the most recent noun, as in “Max or Stan is walking the dog.”

Cumulative adjectives – which are usually from different categories such as age and size – don’t get commas, while coordinate adjectives do. To determine if your adjectives are cumulative, try to either change the order of adjectives or add the word ‘and’ between them. If the meaning is not the same, then they’re cumulative adjectives, as in “a modern Japanese electric car.”

An infinitive is a verb preceded by “to”, as in “to go” or “to teach.” While it is acceptable in speech and informal writing to split infinitives with adjectives, as in “it was hard to completely follow his logic,” it should be avoided in formal writing.

“Who” describes the subject of a sentence, while “whom” is the object. If you can’t figure it out, substitute the “who/whom” pronoun with “he/him” or “she/her.” “Who” will correspond with “he/she,” while “whom” will correspond with “him/her.”

The “kind of” rule is why artists paint “still lifes” instead of “still lives,” and why the “Toronto Maple Leafs” hockey team are not the “Toronto Maple Leaves.” Because a still life is a kind of painting, rather than a kind of life, and the Maple Leaves are a sports team rather than a kind of leaf, their pluralization does not follow the regular rule for pluralizing the words “life” or “leaf.”

Because “none” is derived from “not one,” which is singular, it usually takes a singular verb, as in “none of the pizza is left.” Style guides, on the other hand, agree that none can have a plural verb in some situations, when the “nothing” that the word refers to is plural, as in, “I ordered three pairs of shoes, but none of them are here yet.”

When there are two subjects in a possessive phrase, you must determine whether the two people possess the object together, or separately. For example, in the phrase “Kareem’s and Kumar’s houses are red,” Kareem and Kumar do not share ownership of their red houses. On the other hand, “Kareem and Kumar’s houses are red,” means that Kareem and Kumar share ownership of multiple red houses.

While Latin grammar dictates otherwise, English grammar permits ending a sentence with a preposition. What kinds of grammar snobs have you been hanging out with?

Possessives, such as “Tina’s cat” are formed with reference to the animacy hierarchy, which basically moves in decreasing order of humanness, going from human to animal to inanimate object. The closer to a human that the possessor of the phrase is, the worse the ‘of’ construction sounds. This is why “the cat of Tina” sounds strange but “the hood of the car” sounds completely normal.

Grammar sticklers sometimes maintain that “between” can refer to no more than two things (“between noon and one,” “between Houston and Dallas”) while “among” is used for three or more things or for things that aren’t differentiated individually (“among the pine trees, oaks, and maples,” “among friends”). But “between” is perfectly correct for numerous items. You wouldn’t say “I couldn’t decide among chocolate, vanilla, and strawberry” or “The treaty among Italy, France, and England wasn’t signed.”

The simple distinction is that “I” is a subject, “me” is an object. If you’re tempted to say “My friend and me went to the movies,” try taking your friend out of the equation. Would you say “Me went to the movies?” Likewise, “John met my friend and I at the movies” is wrong – as you’d quickly realize if, again, you left your friend at home (“John met I at the movies???”) And how about “It’s me” vs “It is I?” The latter is correct, strictly speaking, but in practice both are acceptable – and “It is I” sounds stilted and pretentious in anything other than very formal circumstances.