The English language's secret handshake

Karin Ciano, BridgeTower Media Newswires

A new year is upon us, a time we resolve to exercise more, be nicer to people, and improve our writing. Today I’m going to suggest we drill down and look at one small, slippery part of speech: the preposition.

What is a preposition exactly? It’s a word that links two parts of a clause or sentence to show the relationship between them, usually a relationship in space, in time, or of causation. Those of us of a certain age may have learned as schoolchildren the mnemonic that “a preposition shows position.” Typically a preposition lies between the two parts of the sentence that are in relationship: I sit at my desk and type on a keyboard.

Prepositions are the glue that holds sentences together. When used well, they vanish into the background, whispering into the reader’s ear that two clauses have a history and should be viewed together. We hardly notice prepositions—until a mismatched preposition and object walk into a party together and everyone starts talking. (“Did you see dissimilar and from in that sentence? When did she break up with to?”)

You may have noticed that in English, you can’t just match any old preposition with an object: I don’t sit on my desk and type in a keyboard. I talk with (or to, or about) my family on the phone, not the other way around. Other languages deploy fewer prepositions in a structured, regular way, where prepositions in English appear to be plentiful, irregular, and idiomatic. The correct use of prepositions is like a secret handshake that allows one fluent English speaker to recognize another. Yet even among fluent English speakers, confusion may persist: I often think I know which preposition to choose, but the choice can still be anxiety-inducing.

So this year, I’m resolving to do something about it: whenever I feel that nagging doubt about whether I’m using the right preposition, I will pause, and consider my options.

What are they?

First, the easy fix: ask if I even need a preposition. Prepositions make a sentence wordy. Ben (“when you catch a preposition, kill it”) Yagoda suggests using no more than one or two in a sentence; Bryan Garner and the 16th Chicago Manual of Style suggest one preposition for every 10 to 15 words. Style and usage guides offer many tips to eliminate prepositions, which should be the subject of a future column.

But let’s assume that I desperately want to use a favorite word that calls for a preposition, such as the word enamored. Would that be enamored of, or enamored with? Let’s work the problem.

The top 50 to 70 prepositions in English are easy to locate (seriously, just set your search engine hunting for “list of prepositions”), but I have found that lists don’t help me much; in our example, the lists tell me that both of and with are indeed prepositions, information that is both 100 percent accurate and completely useless.

Recall that prepositions can’t be understood in isolation; they signify relationships between companion words or phrases. So instead of looking up prepositions, let’s look up their companions.

Style manuals, usage guides, and dictionaries can be helpful here. The Chicago manual and Gwynne’s Grammar each list words commonly used as antecedents, with directions as to the appropriate preposition match (which may, of course, depend on the object – one inquires into situations, of people, and after people). And when I look up an antecedent in Garner’s Modern American Usage or the Oxford English Dictionary, the proper preposition is often included and discussed.

Do the authorities tell us which preposition enamored is destined to be with? In this case, they do. Drumroll please... the correct usage is enamored of, not enamored with. (Wait a minute, I just ended two sentences with prepositions! Can I do that? Yes, as long as I choose the correct preposition and the phrasing sounds natural.)

I also checked on immune; I’d always understood to to be the right choice, but have noticed immune now seems to split its time with to and from. Most of my authorities say nothing. Garner suggests that the difference is one of nuance: “What you’re immune from can’t touch you; what you’re immune to may touch you but it has no effect.” Somehow, that feels like a nuance in search of a need: it doesn’t really explain why someone can be immune from a lawsuit but immune to the flu. (Sorry readers, but authorities don’t always have a clear answer, or even any answer at all.)

What to do when authorities don’t offer a clear answer?

There’s always the internet. When I started writing this column, I was hoping that technology had advanced to a point where I could simply search for “the prepositionator,” and could download an app would allow me to type in a word and see what prepositions it takes. Sadly, the machines are not there yet.

But we’re getting close. On a whim, I searched Google for enamored, and immediately retrieved a definition with examples using enamored of. A search for immune turned up both immune from (with a legal example) and immune to (every other example). I don’t typically recommend the interwebs as a grammar authority, but it can definitely give you a picture of how other writers are actually using words right now.

And, for that matter, how those words have been used in the past. On the Google Books site called Ngram Viewer, we can search within the text of all the books Google has digitized, going back to books published in the 1800s; for us writing nerds, it’s a fun way to observe how words and phrases have fallen in and out of fashion. It’s also a fun way to pit alternative words or phrases against each other and see which one is more popular. Ngram Viewer shows that enamored of and immune to are clear winners over their alternatives. (Bear in mind that because Ngram Viewer searches all books, not just legal books, it may underrepresent words that are frequently used in the law.)

So, if you’re suffering from preposition anxiety this year, some tips:

Write around the problem. Odds are, you can make your sentence shorter and clearer by expressing the relationship between two words in way that doesn’t require a preposition (for example by using the possessive case).
Look up the primary words, i.e. the ones before and after the preposition. Dictionaries and guides to grammar, style, and usage may tell you exactly which preposition a word takes and under what circumstances.

When all else fails, and you want to be sure you don’t choose something that’s jarringly out of step with current usage, look up the primary words on the internet. For extra credit, try testing possible alternatives against each other using Ngram Viewer—bearing in mind that just because it’s popular doesn’t mean it’s correct.