Ever heard about the time Winston Churchill weighed in on ending sentences with prepositions? According to one of many versions of the story, an editor revised a sentence of Churchill’s so the final word wasn’t a preposition. You know like, “of” or “in” or “at.” Here’s what Churchill had to say about that: 

“This is the sort of bloody nonsense up with which I will not put.”

Or so the legend goes. Churchill probably wasn’t involved in the exchange: The earliest known reference to it doesn’t mention him at all. But no matter who said it, the point is pretty salient: Sometimes, it’s just too awkward to put all your prepositions in the “correct” places. 

Hi, I’m Erin McCarthy, editor-in-chief of Mental Floss. “Don’t end a sentence with a preposition” is one of English grammar’s most infamous rules. But it turns out you don’t actually have to follow it. On this episode of The List Show, we’re splitting infinitives, running amok with object pronouns, and committing some other grammar sins that aren’t really sins at all. Let’s get started.

[Intro]

1. The campaign against preposition stranding—or sentence-terminal prepositions, if you’d prefer—is often credited to two guys in the 17th century. The first was grammarian Joshua Poole, who wrote in a 1646 grammar guide that words should be placed “in their naturall order.” Instead of “What is he good for?”, Poole explained, you should write “For what is he good?”

English poet John Dryden took up that mantle a few decades later in an essay chronicling all the ways that Elizabethan playwrights—including Shakespeare—botched English grammar. According to Dryden, ending a sentence with a preposition was “a common fault” with Ben Jonson. Dryden also copped to committing the error himself sometimes.

But why was it considered an error in the first place? Because 17th-century writers loved to make English mirror Latin—and Latin doesn’t allow prepositions to stray far from their objects. But there’s no grammatical reason you can’t do it in English, and trying to follow the rule makes for some oddly formal and just plain baffling sentences—as illustrated by “up with which I will not put,” up with which I can barely say. English linguists have argued in favor of preposition stranding for centuries.

In 2010, linguist Geoff Pullum got so tired of people’s takes on the matter that he threatened to kill anybody who posted a “boring” preposition comment on his blog Language Log. He was joking … we’re almost positive.

2. The mandate to never split an infinitive has also been linked to Latin influence. An infinitive is the base form of a verb, unbound to any tense or subject—in linguistic parlance, it has no inflection. For example, the verbs in I sing, she sings, and we sang are all inflected. The infinitive form is often (but not always) rendered as to sing. Splitting the infinitive refers to adding a word or words between the to and the verb. As in: I love to loudly sing. You can’t split an infinitive in Latin because the to is implied: To sing is just cantare, so of course loudly would have to go before or after it.

I love to loudly sing does sound a little weird compared to the alternative: I love to sing loudly. But there are plenty of other situations where not splitting the infinitive can change or muddle your meaning. Consider this example that psycholinguist Steven Pinker used to illustrate the issue in a 2014 article for The Guardian: “The board voted immediately to approve the casino.” Here, he explained, “ ... the reader has to wonder whether it was the vote that was immediate, or the approval.” But if you split the infinitive—“The board voted to immediately approve the casino”—it’s clear that immediately refers to the approval.

There’s no hard and fast rule about when not to slap some words between the to and a verb. If it sounds clunky, don’t do it. But if it’s the best way to get your point across, split away.

3. If you’re flanked by a fern on each side, you’re between two ferns. But as soon as a third fern enters the picture, you’re no longer between the ferns—you’re among them. At least that’s what descriptivist grammarians want you to think. According to the rule, you can only ever use between with exactly two items. Between a rock and a hard place, between the devil and the deep blue sea … even between the lines implies that there are two lines. A reference to the number two is baked into the etymology of between. In fact, it even shares an ancient root with the word two.

But there’s no need to take that so literally: Words often evolve away from their origins. Quarantine comes from the Italian for “forty days,” and you don’t see everyone arguing that it’s not really a quarantine unless it lasts exactly 40 days. Between has been used in relation to more than two things since the days of Old English, which seems like an old enough precedent to label it correct. Plus, among doesn’t really have the same effect. As the Oxford English Dictionary puts it, “ … in modern standard English between is the usual word for expressing the relation of a thing to many surrounding things severally and individually, whereas among expresses a relation to an assemblage or group regarded collectively … ” You can easily choose between three restaurants for dinner—but you can’t really choose among three restaurants.

4. Another number-related grammar law is that the word none always requires a singular verb. You’re supposed to say “None of my friends likes pickles”—not “None of my friends like pickles.” As was the case with between, the etymology of none supports this: It comes from an Old English term meaning “not one.” And we can all agree that not one does take a singular verb. You wouldn’t say “Not one like pickles.” Unless you’re an evil pickle emperor, or something.

But as was also the case with between, Old English speakers themselves were known to use none with plural verbs. So it’s hard to argue that we can’t. Not to mention that major dictionaries generally say that none can be singular or plural. The New York Times’ stylebook goes so far as to advise plural in most cases: “Make none plural except when emphasizing the idea of not one or no one—and then consider using those phrases instead.” So when it comes to claiming none is exclusively singular, none of the internet’s armchair linguists have a leg to stand on.

5. For this next one, you might appreciate a light refresher on personal pronouns. If a personal pronoun is the subject of your sentence, you want a subject pronoun: I, you, he, she, it, we, or they (among others). If it’s the object of your sentence—in other words, it’s receiving the action of the verb—you want an object pronoun: me, you, him, her, it, us, or them (again, among others). For instance, you’d say “I saw her”—not “I saw she” or “me saw her.” Well, unless you’re Cookie Monster.

But there’s a big caveat to this rule. When a personal pronoun follows a form of the verb to be—am, were, has been, etc.—it should be a subject pronoun. So, for example, you should technically say “The girl on the train was she” instead of “The girl on the train was her.” This is because to be isn’t an action verb; it’s a linking verb. So when you say “The girl on the train was she,” the pronoun she isn’t receiving any action—it’s just further defining the subject, the girl on the train. In other words, to be is basically the equals sign of English grammar. It is I, The winner was we, and so on.

The only issue with following this rule is that it makes you sound like a knight of olde. So today’s experts generally sanction ignoring it. And thank goodness they do, because “It’s a-I, Mario!” is not a very catchy catchphrase.

6. Let’s pivot from pronouns to adverbs—words that typically modify verbs, though they can also modify adjectives and other adverbs. If an adverb ends in -ly, it’s often describing the manner in which an action was done. You quickly got dressed. I carefully sliced onions. Merrily we roll along. Hopefully falls into this category: Doing something hopefully means you’re doing it with hope. Which is why some grammar sticklers think it’s a travesty to start a sentence with that word. If you say, “Hopefully the gift will arrive on time,” you’re implying that the gift will arrive filled with hope—which isn’t something an inanimate object can really do. And even if the subject of your sentence can experience hope, starting with hopefully can still supposedly leave room for confusion.

William Strunk Jr. and E.B. White certainly thought so, as they explained in the third edition of their classic writing guide The Elements of Style: “This once-useful adverb meaning ‘with hope’ has been distorted and is now widely used to mean ‘I hope’ or ‘it is to be hoped.’ Such use is not merely wrong, it is silly. To say, ‘Hopefully I’ll leave on the noon plane’ is to talk nonsense. Do you mean you’ll leave on the noon plane in a hopeful frame of mind? Or do you mean you hope you’ll leave on the noon plane? Whichever you mean, you haven’t said it clearly.”

That said, hopefully is so broadly understood as “it is hoped” that you almost definitely mean the latter. It’s true that this is a relatively new usage compared to some of the others we’ve covered in this episode: Hopefully as “it is hoped” only started gaining popularity in the 20th century. But dictionaries have given it the gold stamp, and the Associated Press Stylebook validated it back in 2012. Moreover, there’s precedent for deploying adverbs in this way. We even have a name for them: disjuncts, used to “ ... comment directly to the reader or hearer usually on the content of the sentence to which they are attached,” per Merriam-Webster. Other examples include frankly, clearly, and luckily.

That’s all we have on the grammar front for today. Hopefully you’ve learned which rules aren’t worth freaking out about, but if you disagree with anything that we’ve said here, we’d love to hear it in the comments! Just know that we will harshly judge the syntax and grammar of everything you write like we’re Strunk & White. Thanks for watching, and we’ll see you next time.