Ryan Bloom has written for the New Yorker about descriptivism and prescriptivism. The piece makes a few fair points but its overall argument is slightly handicapped by his not knowing what descriptivism and prescriptivism are. There have been fine responses from Ben Zimmer and Nancy Friedman.
I want to give some attention to this passage of Bloom’s:
It [following the rules] does make a difference, at least sometimes. In order to determine when those times are, the question must be asked: For whom are you writing? Take that last sentence, for example. … Its ostentatious structure and secret message says, “I am one of you.” It also says even sneakier things like “I’m educated, an authority,” and “You can trust me about language usage.” The average New Yorker reader recognizes the effort the sentence exerts to maintain grammatical correctness, and in recognizing this, the reader bonds with the writer.
This, even if it might be a bit tongue-in-cheek, suggests a writer with supreme grammatical confidence. So let’s look again at his prize sentence:
In order to determine when those times are, the question must be asked: For whom are you writing?
How does that sound to you? I don’t mean the “for whom”; that’s fine in the context of a more formal register. I mean the first part.
To me it sounds clunky. But worse, the reason for its clunkiness is its grammatical weakness.
Here’s section 5.107 of the Chicago Manual of Style (16th edition), on dangling infinitives, written by Bryan Garner:
An infinitive phrase can be used, often loosely, to modify a verb—in which case there must be an express or implied logical subject in the sentence. If there is none, then the sentence may be confusing. For example, in to repair your car properly, it must be sent to a mechanic, the infinitive repair does not have a logical subject; the infinitive phrase to repair your car is left dangling. But if the sentence is rewritten as to repair your car properly, you must take it to a mechanic, the logical subject is you.
Bloom has dangled his infinitive, a subjectless “to determine” that leads us nowhere. The problem is easy to fix. For instance:
In order to determine when those times are, you must ask the question: For whom are you writing?
In order for those times to be determined, the question must be asked: For whom are you writing?
They vary in their levels of pomp (and in specificity about who’s asking the question), but in both of them the symmetry and flow are improved.
You might hesitate to follow Garner and Chicago in endorsing an absolute ‘thou shalt never dangle an infinitive’ decree. But here, this aspect of Bloom’s sentence is the reason it clunks so. He wanted an “ostentatious structure” but his reach exceeded his grasp. The “effort the sentence exerts to maintain grammatical correctness” is all in vain.