We spend a lot of time discussing grammar rules here, so you might be surprised to learn we don’t actually like every grammar rule. The primary purpose of language is communication, so any rule that makes doing that more difficult or muddles people’s understanding is counterproductive. How people communicate today has changed from how they communicated decades ago, and in some cases, a guideline now seems out of date. If a grammar rule is routinely causing confusion, maybe the rule is the problem, not the speaker (or writer). So let’s loosen up a little — which grammar rules would you change?

Old-fashioned grammar rules say not to end a sentence with a preposition (including “with,” “at,” “for,” and “about”), but try applying that rule in regular conversation and see how unnatural it feels. “What are you talking about?” becomes “About what are you talking?” and “Who are you going with?” turns into “With whom are you going?” It sounds outdated and stilted. The preposition rule arises from attempts to force Latin grammar rules onto the English language, and the wording sounds awkward because we’re trying to fit a square peg into a round hole. Most modern style guides agree that it’s fine to end a sentence with a preposition if it sounds more natural that way. We’re in favor of letting this rule go for good.

Is it time for “whom” to fade into retirement with “thee,” “thine,” and “thou”? Technically, “whom” is the object pronoun form of “who,” meant to be used when someone is receiving the action of the verb. For example: “To whom should I address the letter?” But most people don’t think about sentence structure that way mid-conversation — or mid-email. In casual speech and writing, “who” has pretty much taken over, and even grammar sticklers are starting to let it slide. “Whom” often adds formality where it’s not needed and can sound stilted or awkward. We won’t judge you if you let this one slide. 

We were taught by writing teachers to fear the passive voice like it’s a grammatical boogeyman, but here’s our controversial take: It’s fine. As a quick refresher, passive voice is, “The ball was thrown by her,” while active voice is, “She threw the ball.” The active voice sounds stronger and more direct, but that doesn’t mean the passive voice is always wrong. “The dog was groomed,” for example, sounds better than “The groomer groomed the dog.” And in fact, science writing, legal documents, and formal reports often use passive voice to keep the tone objective: “The experiment was conducted under controlled conditions.” Other times, you don’t know who did the action, or it doesn’t matter: “A mistake was made.” There’s no need to twist yourself into knots in an effort to correct every instance of passive voice, especially because sometimes it makes sense stylistically.

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Traditional grammar rules say you should never split an infinitive, meaning the “to” and the verb should stick together. Inserting any word (usually an adverb) in between them is considered incorrect. By those standards, Star Trek’s epic tagline — “to boldly go where no one has gone before” — would be a sanitized “to go boldly…” In this example, splitting the infinitive adds unforgettable panache. Sometimes a split infinitive is needed to change the meaning altogether. “She decided to gradually back away” has a different meaning than “She decided gradually to back away.” We could write, “She decided to back away gradually,” to avoid the split infinitive, but we think breaking the rule is worth it for the flow of the writing. So go ahead — dare to boldly, unapologetically split your infinitives. Just don’t get carried away and start flipping every sentence around, or you’ll end up in Yoda territory — and that’s Star Wars, not Star Trek.

I was introduced to the word “cul-de-sac” via an elementary school birthday party invitation. I found out that people didn’t just live on roads, streets, avenues, and lanes — they could also live on something named for a fancy French word, a cul-de-sac. “Cul” is an interesting word in French — it’s a rude slang word for someone’s rear end, but it’s used in some other contexts to refer to the end of something. The second half, “de sac,” means “of the bag” — so the literal translation of “cul-de-sac” is “bottom of the bag.” As a compound word, however, “cul-de-sac” means “dead end.” American housing developers borrowed it from French to name streets that are basically dead ends, where a few houses line the end of a road that goes nowhere. In planned subdivisions, they’re popular for privacy, parking, and a neighborhood camaraderie feel. 

But say you live in a neighborhood that has many of these dead-end streets and your neighborhood association is trying to decide which one should host the summer block party. The correct pluralization of this compound word is “culs-de-sac,” not “cul-de-sacs.” While it may seem puzzling, it follows a grammar rule that affects many English words: In compound words, the chief element is pluralized, not the entire phrase.

Sure, the English language has plenty of irregular plurals, but in most cases, a suffix of “-s” or “-es” will suffice. But compound nouns — those formed by combining two or more words into one concept — aren’t as cooperative. You have to worry not only about what suffix to use, but also about where to use it. For instance, the “-s” suffix to pluralize “cul-de-sac” comes after the main noun “cul,” as in “culs-de-sac.” 

This applies to other compound nouns, too. For instance, “mother-in-law,” “son-in-law,” and all other “in-law” honorifics are pluralized with an “-s” after the main noun, not the whole word. So, the correct terms are “mothers-in-law” or “sons-in-law.” Compound nouns made up of a main noun and a modifier, such as “passer-by,” “runner-up,” and “court-martial” get the same treatment — the correct plurals are “passers-by,” “runners-up,” and “courts-martial.” However, two-headed compound words, composed of two equal nouns (no modifier), tend to hyphenate only the final noun, as in “city-states” and “singer-songwriters.” 

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But it’s not only hyphenated compound words that face muddled pluralizations. Open compound words (featuring a space between words) also pose problems. “Surgeons general” and “chiefs of staff” are the correct plural forms because the main noun is pluralized, not the modifier. That said, you can likely get away with some pluralization missteps in casual conversation — a friend likely wouldn’t reprimand you for saying “sister-in-laws” or “cul-de-sacs.” 

Picture this: You’re hosting a friend for dinner, and you ask, “What do you want to eat?” They shrug and say, “Whatever you’re cooking!” They’re open to anything, from spaghetti to mystery meatloaf. The options are unlimited, so “whatever” fits the bill.

But later, your friend is eyeing your bookshelf for something to read. They’ve narrowed it down to a few novels, and they look at you expectantly. You say, “Borrow whichever book you’d like.” Bingo — this is the correct response for this context. But why choose “whichever” instead of “whatever” here? “Whichever” and “whatever” aren’t twins — think of them more as distant cousins. It’s a simple rule, but it’s also easy to see how the two can be mixed up: “Whichever” indicates a specific set of choices, while “whatever” implies something undefined. 

You might wonder if, in the library context, “Borrow whatever book you’d like” is an acceptable response. In casual conversation, yes, but if you’re trying to appease your English teacher, no. Sure, both words are about making choices, but the type of choice matters. According to the New Oxford American Dictionary, “whichever” emphasizes a lack of restriction “in selecting one of a definite set of alternatives.” In contrast, “whatever” emphasizes a lack of restriction “in referring to anything or amount, no matter what.” In simpler terms, “whichever” should be used for known or limited options, and “whatever” is more appropriate for unknown options.

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Here’s another example of this linguistic fumble: “Whatever team wins tonight will go to the playoffs.” This is technically incorrect — it should be “whichever team” because there are limited options of two teams. However, you might add, “Whatever happens, we’ll still have fun watching,” which is grammatically correct because there are infinite options for what might transpire. This is why the sentence, “Whichever happens, we’ll still have fun watching,” is wrong. So, whether you’re choosing between books, teams, or dinner options, remember this rule: Use “whatever” when your options are unlimited and “whichever” when your options are limited.

What defines a “good” paragraph? Some English teachers would say it must be at least three sentences — enough for an introduction, a supporting sentence, and a transition — but that isn’t always true. The rules of paragraph structure are widely disputed in writing instruction, particularly regarding the guidance that every paragraph should be three to five sentences. While some champion this method as a way to teach students to write cohesive paragraphs, others call out its limitations. Ken MacRorie, author of the influential creative writing book Uptaught, says that “formula-style” essay structure forces students “to write mechanically instead of self-expressively.”

If the guidelines around paragraph length seem unclear, that’s because they are. Even academic institutions diverge in their recommendations. Purdue University’s College of Liberal Arts, for example, suggests three- to five-sentence paragraphs, aligning with what many of us were taught in school. The University of North Carolina at Chapel Hill’s Writing Center offers a more flexible approach, noting that short paragraphs are permissible in certain contexts, such as journalism, and explaining that occasionally, “a paragraph can be just one sentence long.”

The leading international editing company Cambridge Proofreading similarly highlights a variability in paragraph length across different writing styles. Per its recommendations, academic writing follows the strictest guidelines, requiring three to eight sentences (or more) with a clear introduction and a conclusion/transitional sentence. These are the structured paragraphs that many students learn to write in English courses.

However, Cambridge believes the rules can be more lax in professional and business writing, where brevity and clarity are valued. In these contexts, the company recommends aiming for two to four sentences, with single-sentence paragraphs used sparingly for emphasis. Creative writing, meanwhile, seems lawless compared to other writing styles. A paragraph can be whatever an author wants — long, short, or fragmented. In modern digital content, such as blog posts and online articles, short paragraphs are the norm. One- to three-sentence paragraphs enhance readability and break up “walls” of text to prevent overwhelming the reader. 

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Given these variations, Cambridge editors advise writers to consider the audience and the medium when determining paragraph structure. When in doubt about where to break your writing, remember that the purpose of a paragraph is to convey a single main idea, regardless of how many sentences it takes to complete it.