“This is the kind of nonsense up with which I will not put.” ~Winston Churchill

We’ve all been told countless times by English teachers and grammar pedants that it’s bad form to end a sentence with a preposition. And yet, often, trying to avoid this supposed grammar faux pas often leads to awkward and ungainly sentences, like the one quoted above. In speech especially, rewording a sentence to avoid this supposed “dangling preposition” sounds stilted and unnatural. The song Cotton-Eye Joe wouldn’t flow nearly as well without the phrasing “Where did you come from?” This is despite the fact that in formal English, the “correct” construction would be “From where did you come?”

Writing, however, is more formal than speech. So how do you decide on the proper balance between the flow of your words and avoiding too much informality in your work?

Well, first, it’s important to understand what exactly a preposition is. A preposition describes the location or time, or other characteristic of the noun or noun phrase that is its object, often in relation to another noun or verb in the sentence. I went to the store. I bought a gift for my boyfriend. In the first sentence, to is a preposition, the object of which is store. In the second, for is a preposition, the object of which is my boyfriend.

Notice that the object of the second preposition is a two-word phrase, rather than simply a noun. A noun phrase consists of a noun plus any number of modifiers—adjectives, articles, even subordinate clauses.

We learn in school that words like to, for, with, and up are prepositions, and are always prepositions, because part of speech is an inherent characteristic of a word. But this isn’t entirely accurate. Language is messy and complicated, and words don’t always fit into neat categories. Think of the sentence, “The girl hung up the painting.” Is painting the object of the preposition up? Of course not. It’s the object of the phrasal verb, to hang up. So what function is up playing in this sentence if it’s not actually a preposition? Well, we could call it an adverb, since it’s sort of kind of maybe modifying the verb to hang. How did she hang it? She hung it up. But it’s not really an adverb either. Really, it’s part of the verb itself, as in the phrasal verb to put up with. Putting up with something isn’t just a modified version of putting, any more than understanding something is a modified version of standing.

So why the confusion? Why teach us something that is inaccurate?

Up until a few hundred years ago, English didn’t have a formal grammar. A bunch of intellectuals decided that one should exist, because Latin had one; and since Latin was their example, it was Latin grammar that they imposed upon English. But English is a Germanic language, not a Romance language, and doesn’t follow the same linguistic patterns as Latin. They were forcing a square peg into a round hole, and ever since then grammar prescriptivists have been insisting that we’re speaking our native language incorrectly.

It only takes a bit of introspection to realize that this prescriptivist approach to grammar, which insists that part of speech is an inherent characteristic of a word, is laughably wrong. In English, the infinitive is formed by using the word to plus the verb stem. To be, to go, to hang. To can’t be a preposition in these cases, because the following word is a verb, not a noun. In addition, sometimes what looks like a preposition is actually a conjunction. In the sentence “I do my homework after school,” after is a preposition, the object of which is school. However, if I were to say, “I’ll check my Twitter after I finish my homework,” after is a conjunction. I finish my homework is a complete sentence in and of itself, rather than a noun or noun phrase.

So how do you determine whether a preposition is actually a preposition? One way is to try to identify the object. If what comes after it isn’t a noun or noun phrase, it can’t be a preposition. This doesn’t work as well with phrasal verbs, which do take nouns or noun phrases as objects—specifically, as the direct object of the verb. In this case, you can ask yourself whether you’d define the verb based on the conjugable form, or by the phrase as a whole. Put, put up, and put up with all have different meanings—you wouldn’t just define put and leave the rest of the phrase out of the definition.

Back to ending sentences with prepositions. By their very nature, prepositions require the object to come after them. The word itself comes etymologically from the idea of placing (posit) before (pre). (Some languages, like Hindi, have postpositions, which perform the same function as prepositions but come after the object, rather than before.) Since prepositions require an object, and that object comes after the preposition, it doesn’t make sense to end a sentence or clause with a preposition. Yet, in speech, often we do, even when the preposition is acting as a preposition.

Take this sentence, from one of my previous posts: “It’s a string of sounds to which a group of humans have ascribed an agreed-upon meaning.” The flow is pretty good, and I’d probably word it that way even in everyday speech, but then, I’m the kind of person who uses “ascribe” in casual conversation. Consider this variation: “It’s a string of sounds a group of people have ascribed meaning to.” Still sounds like a perfectly reasonable sentence, right? Possibly even a better sentence than the first one, if we’re talking about speech rather than writing.

Does that mean to isn’t actually functioning as a preposition? If it is, where is its object? Maybe it’s a phrasal verb, ascribe meaning to.

Except that’s not the case. The verb is ascribe, while meaning is the direct object—the object of the verb, which would be in the accusative in languages like Latin and Russian. The object of to is which, the relative pronoun that refers to the subject of the sentence. In the second version, the which is omitted as being unnecessary, but it’s still implied, as the indirect object of the verb. In English, the indirect object can come between the verb and the direct object, as in the sentence “I gave my boyfriend a present,” or it can be the object of the preposition to or for, as in “I bought a present for my boyfriend, and then I gave it to him.” In Latin—the language from which the pedants drew all those tiresome grammar rules—you couldn’t end this sentence with a preposition, because the indirect object is indicated by the use of the dative case (which survives vestigially in English pronouns, as in “I gave him a present”), rather than with a prepositional phrase. So you would have to include the pronoun which, with the dative ending.

Now that we’ve covered what exactly is a preposition and what is not, what are the rules for ending sentences with prepositions in your writing? In formal writing, avoid it where possible. Even in the case of a phrasal verb, you should shy away from ending a sentence with something that looks like a preposition, if only because it will cause a certain percentage of your readers to judge you.

In fiction writing, the rules are more fluid. For dialogue, think about what your characters would actually say. Are they like me, where they reword even their everyday speech to avoid breaking this arbitrary rule? Or are they more prosaic in their speech patterns?

How about in the narrative? Well, that depends on the point of view of your novel. If it’s first person point of view, consider whether your narrator would differ in their writing from what they would say in everyday conversation. For omniscient third person point of view, it’s probably best not to end sentences with prepositions at all. For limited third person, you have a bit more leeway, based on what feels more true to the narrator’s character and internal dialogue.

The important thing is to remain true to your character’s voice without sacrificing meaning, clarity, and flow. Feel free to ignore the dictates of prescriptivist grammar if that works better for your story. In cases where you think it would be best not to end the sentence with a preposition, or pseudo-preposition, consider whether there’s another verb you could use in the place of the one you originally chose—for instance, the quote at the beginning of this post could become “This is the kind of nonsense I will not tolerate.” Alternatively, try to figure out the actual or implied object of the preposition, and move the preposition to that part of the sentence, e.g. “That’s someone I’d like to hang out with” could become “That’s someone with whom I’d like to hang out.” Just be sure to avoid awkward phrasing that interrupts the flow of the narrative. Ungainly restructuring of sentences is something up with which you should not put.