Answers to Questions About Prepositions

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Here are several questions from DailyWritingTips.com readers about use of prepositions, and my responses.

1. I was always taught, “Never use a preposition to end a sentence.” For example, “I want to go with” should be “I also want to go,” or “Use the dustbin to throw the rubbish in” should be “Throw the rubbish in the dustbin.” Yet you have done so with the word out in the sentence “California gave a record $100 million loan to bail schools out.” Is it OK to end sentences with prepositions?

The admonition to never end a sentence with a proposition has no valid grammatical basis: For example, “She was the one he wanted to go out with” is correct. (Here is one of several DailyWritingTips.com posts on the topic.) Earlier placement of a preposition in a sentence makes the sentence sound more formal, but efforts to consistently do so sometimes result in awkwardly stiff syntax, as in “She was the one out with which he wanted to go.” (However, “I want to go with” is a different matter; as a truncated version of “I want to go with you,” it’s colloquial and not suited for formal writing.)

2. I am reading a very well-written book, but I’ve run across an expression that grates: The author wrote at least twice of “a couple weeks” or “a couple trees” (or whatever), where I have always said “a couple of.” I can’t figure out which expression is the correct one. Have you covered this, or can you advise me?

This post is one of several at DailyWritingTips.com that discusses couple. “A couple of” is the correct form, but either the author chose to be colloquial, or neither he nor his editors know the correct usage.

3. I have always thought that “outside of” is incorrect when used this way: “The man was outside of the house” (as opposed to “The man was outside the house”). Am I right?

Using the preposition of is usually superfluous in such constructions, but it’s not incorrect, and in the senses of “besides” and “apart from,” it’s necessary. Some grammar handbooks advise playing this usage by ear.

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20 thoughts on “Answers to Questions About Prepositions”

  1. I have a query related to one of the examples you used:

    Shouldn’t the proper (if stiff) syntax of “She was the one he wanted to go out with” actually be “She was the one with which he wanted to go out”? The way you arranged it skews the meaning for me.

    Thanks for your reply!

  2. Re #3: Outside of a dog, a book is a man’s best friend. Inside of a dog it’s too dark to read.

    Groucho Marx

    P.S.: My most recent blog post tells why learn the English you should!

  3. I don’t agree with dismissing the quite widely accepted rule of thumb not to end a sentence with a preposition.

    It’s certainly true that there are a few rare situations in which following the rule results in awkward, if not downright absurdly awkward, sentences, but the attempt should be made. Such sentences mark one of the many differences between one who communicates an idea and a professional writer who not only communicates an idea, but also does it in such a way as to make it memorable, to make it linger.

    If I encounter a sentence ending with a preposition and if I can rewrite the sentence to avoid the offending preposition and if the resulting sentence isn’t at all awkward, I know that I’ve come across yet another lazy or incompetent writer—someone on Tucker Max’s level.

    Ignoring the rule certainly works for many, but it doesn’t follow that the product will impress or inspire. After all, if I write that “I ain’t got no money,” I’ve communicated the idea, but not tempted anyone to hire me to do their taxes or manage their inheritance.

    One’s writing is as important as one’s physical presentation at an interview. Shabby clothes, an unwashed face, disheveled hair, body odor, a stubbly beard—all convey a notion of one’s lack of professionalism. Lazy, incompetent writing does the same, yet fewer and fewer readers are qualified to judge professional writing.

    The times have debased many objective standards and those who should know better would rather accept the unacceptable than admit that they have no idea of what’s acceptable and what’s drivel.

    The author’s writing “to never end” and “to consistently do so” rejects the widely accepted rule of thumb not to split an infinitive—an infraction that still riles many readers. It would have been easy to proof and change those two examples before publication, but that wasn’t done.

    Again, many writers find it easier to break a widely accepted rule than to work a bit harder at their profession to find a way to accommodate such rules while avoiding inelegant sentences and awkward wording. That’s the whole point of “professional”: do what needs to be done even if others don’t see the need.

  4. “California gave a record $100 million loan to bail schools out.” Is it OK to end sentences with prepositions?

    This could be fixed very simply by rewriting the sentence:
    California gave a record $100 million loan to bail out school.

    I agree totally with Matt’s comments.

  5. Re Matt Gaffney’s comments: Being “professional” also requires one to keep up with developments in one’s chosen field. Mr. Gaffney has failed to do that. The Chicago Manual of Style dismisses the “rule” about split infinitives thusly: “Although from about 1850 to 1925 many grammarians stated otherwise, it is now widely acknowledged that adverbs sometimes justifiably separate an infinitive’s to from its principal verb {they expect to more than double their income next year}. [Section 5.106] The AP Stylebook echoes this sentiment: “AP guidance is to avoid awkward constructions that split infinitives or compound forms of verbs.” In “Woe Is I,” Patricia T. O’Conner says “This ‘rule’ was popular for half a century, until leading grammarians debunked it.” And Bill Walsh, in “Lapsing Into a Comma,” says simply “Split Away!”
    On the matter of ending sentences with a preposition, Mr. Gaffney (and Ms. Bahner, by her endorsement thereof) are also outside of current grammatical practice. Chicago says this:
    5.176 The traditional caveat of yesteryear against ending sentences with prepositions is, for most writers, an unnecessary and pedantic restriction. As Winston Churchill famously said, “That is the type of arrant pedantry up with which I shall not put.” A sentence that ends in a preposition may sound more natural than a sentence carefully constructed to avoid a final preposition. Compare, for example, ‘this is the case I told you about’ with ‘this is the case about which I told you.’ The ‘rule’ prohibiting terminal prepositions was an ill-founded superstition. Today many grammarians use the dismissive term pied-piping for this phenomenon.” And O’Conner observes that “. . . great literature from Chaucer to Shapespeare
    to Milton is teeming with sentences ending in prepositions.”
    In conclusion, I’m inclined to align myself with the professional writing skills of Churchill, Chaucer, Milton, and Shakespeare”; that’s an august group of brilliant writers who knew the difference between valuable linguistic rules (which I endorse and practice daily) and antiquated, obsolete non-rules that contribute little to the clarity and richness of written communications.

  6. But after all the grammar history and hoopla and aligning ourselves with august writers,

    “California gave a record $100 million loan to bail out schools.”

    has more clarity and richness than

    “California gave a record $100 million loan to bail schools out.”

    No one had to jump through hoops to make it work. It’s just simple editing that I agree


  7. Even though I consider myself a good writer, it always amazes me how little I really know about proper grammar skills. Just wanted to thank you for being there, reminding me of my shortcomings!


    Kirk Carter

  8. Here’s what that has bothered me for quite some time. Is it (for comparison):

    I will try and fix that


    I will try to fix that.

    The first implies, at least to me, that you will both try and do the action.

    The second implies that you will attempt to perform the action.

  9. I don’t know much about antique Anglo Saxon, Old English, Middle English, or Dutch. However, it is true that modern German abounds with sentences that end in prepositions. There is even something called a “removable prefix” that goes on some verbs, and most of those prefixes are prepositions.

    Just that suggests to me that sentences that end in prepostions are common features of Germanic languages. Also, despite the fact that English contains hundreds of thousands of words from Old French, Middle French, Latin, and Greek, our grammar is mostly Germanic.

    The German prepositions that can function as removable prefixes include { ab, an, auf, aus, bei, in, nach, ober, uber, um, unter, vor, wider, wieder, zu }.

    By the way, if you have ever heard Sergeant Schultz call our “Raus!” to the prisoners, that is short for “heraus”, and that is a combination of “her” and “aus”. Hence, it means “Out here!”.
    It doesn’t have anything to do with waking up.

  10. The reason for calling some prefixes “removable” in German is that in the infinitives, present participles, and past participles of verbs, the prefix is right where you would expect it: one the front of the verb, such as in “ausfahren” = “to drive away from”.

    German also has some other prefixes that are fixed prefixes on verbs, and they stay right where they go, just like in English prefixes on verbs.
    To confuse things even more, there are other prefixes that are sometimes fixed prefixes and something removable prefixed, depending on the exact use of the verb. For example, it can make a difference if the meaning of the verb is literal or figurative.

    I am always happy that we do not have to bother with any of this in English. If you want to put a prefix on a verb, you just “nail it on”, such as in beset, inset, offset, onset, uotset, reset, and upset.

  11. My sole focus regarding split infinitives and sentences ending with prepositions was that good writers should avoid awkwardness and should write elegantly.

    The Chicago Manual of Style cited by Phil Radler cautions that “. . . adverbs sometimes justifiably separate an infinitive’s to from its principal verb,” i.e., infinitives are “sometimes” justifiably split. In that caution, “sometimes” is not a minor player.

    Also, “AP guidance is to avoid awkward constructions that split infinitives or compound forms of verbs . . . . [c]ompare, for example, ‘this is the case I told you about’ with ‘this is the case about which I told you.’” Both examples are deliberately awkward. What’s wrong with “I told you about this case”?

    Of course writing styles change over time, but that’s not the issue in my mind. I believe that good writers can write quite well within the so-called rules that have been widely accepted for decades. Those who find those rules too challenging never say “I’m not up to it”; they say that the rules are outmoded and unnecessary. It is far easier to dismiss as unnecessary whatever one cannot do than to work harder to comply and succeed; it is the difference between “settle” and “aspire.”

    The narrative technique of the stream-of-consciousness style frequently and unavoidably violates the widely accepted rules, but its champions (Joyce, Woolf, Proust, Faulkner, et al.) don’t dismiss the rules as outmoded and unnecessary. Instead, they created their own rules within which they worked quite successfully, abiding where they could to the tried and the true and then off on a tear when the situation required.

    I can’t tell from Phil Radler’s citing the Chicago Manual of Style if he or the manual itself described the “. . . ‘rule’ prohibiting terminal prepositions . . . [as] . . . an ill-founded superstition,” but somehow I can’t imagine that the editors of the Chicago Manual of Style would use “superstition,” i.e., “a belief or way of behaving that is based on fear of the unknown and faith in magic or luck; a belief that certain events or things will bring good or bad luck” in that context.

    I certainly applaud Phil Radler’s aligning himself with the likes of Churchill, Chaucer, Milton, and Shakespeare and I’m sure that Mr. Radler’s writings will be praised long after we have forgotten about Churchill, Chaucer, Milton, and Shakespeare, but not until then.

  12. I, too, have come across the “a couple dogs” or “a couple times” in which the “of” has been omitted. However, I have seen it repeatedly in one newly published fiction book after another. The “come with” issue pops up quite often, too. Assuming the vast majority of publishing houses are in the north, could this be a northern dialect issue, so they see nothing wrong with it? I’m in the south, and we definitely don’t talk like that. (Yes, we have our own issues.) When I come across this type of writing, it pulls me out of the story as I re-read to make sure I read it correctly. That’s simply not good writing if it pulls the reader out of the story.

  13. I’m somewhat baffled at the unseemly hostility embedded in Mr. Gaffney’s comments (both his original snarky remark about “lazy and incompetent writers” and his subsequent crack about my writings, of which he knows little). But let’s deal with the issues as they stand:

    1. Since he didn’t bother to check it himself (although that’s what professionals do), I’ll repeat the exact text I extracted from the Chicago Manual of Style Online, 16th edition, section 5.176:

    The “rule” prohibiting terminal prepositions was an ill-founded superstition. Today many grammarians use the dismissive term pied-piping for this phenomenon.

    2. Mr. Gaffney offers an alternative phrasing to one cited example, saying
    What’s wrong with “I told you about this case”?
    What’s wrong is it changes the meaning. The original example was obviously separating the instant case (“This is the one I told you about”) from one or more other cases. Mr. Gaffney’s version loses that point entirely.
    3. In aligning myself with those distinguished writers, I only meant to imply that I would cleave to their guidance rather than to Mr. Gaffney’s, since he hasn’t kept up with the linguistic evolution reflected in the Chicago and AP Stylebook extracts (and I could cite others whose credentials are far better known than Mr. Gaffney’s). I harbor no delusions about my writing skills. But at least I do try to stay informed, and I do try to exchange ideas with others in a friendly, collegial manner. Perhaps instead of referring Mr. Gaffney to the subtle insights of the Chicago Manual of Style, I should have proffered instead a link to Emily Post.

  14. Matt Gaffney: I am not one for ditching the rules simply because a lot of people don’t know or obey them, but I think you have to distinguish between actual rules and misguided dictats. As mentioned in the article, the ban on terminal prepositions, as well as on splitting infinitives were never legitmate “rules” of English grammar to begin with. As I recall, these are rules of Latin grammar that were arbitrarily (and that is key) imposed on English by Latinophiles for a brief period in the history of the language for no good cause. There is simply no reason, in English, for such rules. Observation of them can obscure meaning or force awkward construction, often—not just occasionally or seldom. Frequent enough, really, for the “rule” to be abandoned for that reason alone.

    “One’s writing is as important as one’s physical presentation at an interview. Shabby clothes, an unwashed face, disheveled hair, body odor, a stubbly beard—all convey a notion of one’s lack of professionalism.”

    True, but not observing a phony rule is none of those things. Someone who says, “That is where I came from” and not, “That is from where I came” is not being lazy or incompetent. He is also not being pseudo-pedantic and downright silly. Yes he could re-word it, but there is no need to. He could say, “That is whence I came.” But that sounds even more affected and there is absolutely nothing wrong with using “from where” instead of “whence”. Likewise the stylings under discussion. Similarly ,“I didn’t mean to really scare you” and, “I didn’t really mean to scare you” are both not only fine, but mean different things. Impressive, inspirational, or *professional* writing is not a function of stilted language or imaginary grammar. Quite the opposite. These two “rules”, specifically, are not objective standards and in reality never have been.

    I am reminded of a girl in the fourth grade who aggressively scolded other students for failing to put a horizontal bar across the tops of their upper-case Js. She was convinced that the rules mandated a barred J, and ommitting it was no different from doing the same to a T. But she was wrong. There is no such commandment for Js. Though the bar is fine as flourish it looks odd and detracts from the content of Jack or Jill. (Who is Tack? Inevitably.)

  15. A lot of good ones. I usually don’t bother to go to the website for the real thing, after getting the e-mail ‘tip’.

    I’m surprised that no one recounted the old one about the farm boy arriving at Harvard (on a scholarship of course).

    He pulled his truck u p to a senior student lolling around the Yard and called out: “Hey bud. Kin you tell me where the Administration Building’s at?”

    The response of course was something like: “Here at Haaavaaad we don’t end sentences with a preposition.”

    “OK. Then . . . kin you tell me where the Administration Building’s at — Asshole?”

    (I’ve always loved that one, especially since it was told to me by a Harvard graduate.)


  16. I like the one where the 2 southern college boys are trying to chat-up a couple of Ivy League young lovelies.

    The men: “We go to ta Ol’ Miss. Where do y’all go to school?”

    The women (noses pointing up): “Yale”

    The men (as loudly as they can): WE SAID” WHERE DO Y’ALL GO TO SCHOOL!”

  17. Mr. Gaffney offers an alternative phrasing to one cited example, saying
    What’s wrong with “I told you about this case”?
    What’s wrong is it changes the meaning.
    Indeed, and agreed. And, not to pile on, but there is absolutely nothing wrong with, “This is the case I told you about”. It is neither lazy nor awkaward, and does not display any grammatical offense. To refer to the preposition rule in question as more a superstition than a rule is fairly acccurate.

  18. As Dale A. Wood wrote, many German verbs have prefixes attached to them, either separable or inseparable. As is happens, the separable prefixes resemble prepositions (even if they aren’t *actually* prepositions). In all but the simplest constructions, the separable prefix is detached and moved to the end of the sentence or clause.

    My theory is that German separable prefixes are the source of sentence-final prepositions in English. When there’s an established meaning for the verb-prepositon pair, it often “just feels natural” to put the preposition last.

    A bunch of British scholars, who’d been required to study Latin, felt compelled to shoe-horn Latin grammar rules into their native tongue, ignoring the fact that English is a Germanic language, not a Romance language. Perhaps the most infamous example is, “A preposition is something you should never end a sentence with.”

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