Published on October 5, 2025 11:23 PM GMT

When I was a child in school, punctuation marks were taught like rules. A period goes at the end of a sentence. A comma is useful because a list like “Apple banana cherry” is wrong; the list “Apple, banana, cherry” looks better. If you don’t use commas or periods or ‘and’ or ‘but’ enough, but simply write the things you want to write without bothering with demarcation, you get a run-on sentence. Some words should start with a capital letter everywhere; also the letter at the beginning of a sentence should be capitalized. Semicolons; hyphens and dashes; ellipses. Parentheses. Forward-slashes.

It makes sense to teach them to children as rules, first, and of course they do have rules attached to them. One may talk of expression and experiment, but nothing ever justifies using a parenthese her)e. But at the same time, there is wonderful flexibility in which you choose to use where. Consider the following examples.

He was going to be late again (and again no one would notice).

He was going to be late again; and again, no one would notice.

The parentheses version makes it seem like the subject is getting away with something unimportant. I’d use it if I were writing about a man who, say, has a flexible office job, where you can arrive whenever.

The semi-colon-comma version has more weight; I’d use it about a man who, let’s say, was having trouble with his family. Perhaps he arrives late to dinner, and they barely even notice or care. A heavier situation, so the heavier version of the sentence works better.

I don’t see how that’s relevant.

I… I don’t - see how that’s relevant.

The former, confidently dismissive. Spoken by someone in control. The latter, flummoxed, unsure. A debater who knows his opponent has just gotten one over on him in front of everyone. A cheating spouse, after evidence has been discovered. Ellipses - just a group of periods, really - and dashes, used to evoke the pauses of speech that can happen when communicating orally. The confident / unconfident difference is also present in this contrasting pair:

No.

No!

Trump Case: the idiosyncratic capitalization choices made by Trump when he writes. Examples are absolutely everywhere; here’s a Truth Social post of his from a couple hours ago^[1]:

The Soybean Farmers of our Country are being hurt because China is, for “negotiating” reasons only, not buying. We’ve made so much money on Tariffs, that we are going to take a small portion of that money, and help our Farmers. I WILL NEVER LET OUR FARMERS DOWN!

All-caps emphasis is common enough, but Trump Case is fun and unusual. Farmers get a capital letter to start with, so does Country; Tariffs too. But it’s not like he capitalizes every noun: ‘money’ isn’t capitalized, and in longer excerpts there are plenty of uncapitalized nouns.

Compare to normal-case:

The soybean farmers of our country are being hurt because China is, for “negotiating” reasons only, not buying. We’ve made so much money on tariffs, that we are going to take a small portion of that money, and help our farmers. I will never let our farmers down!

I don’t fully understand the choices made when doing Trump Case, but maybe “soybean farmers” seems a little random here when normal casing? Promoting them to Soybean Farmers gives a little bit of oomph - it makes them a class, a people, rather than the word ‘farmers’ modified by an adjective.

I believe that in Trump’s linguistic mind (and make no mistake, he is one of the most interesting linguistic minds of our day, and I’ve thought this for ten years now, even back when I was voting for his opponents), there are nouns, proper nouns, and Important Nouns. How to give emphasis to this new class of Important Nouns? In speech it’s easy, and you hear it in his voice when he speaks, this emphasis (or anyone’s voice, emphasizing the important nouns in a sentence is a very common element of speech); but in writing it’s not clear how to do it.

So: you want to write the above quote (the normal-cased version) while emphasizing some nouns and not others. There are other ways to do it; perhaps by saying more about why soybean farmers are important, and allowing the term to appear twice at the beginning:

America’s farmers are critically important; from corn farmers to soybean farmers. The soybean farmers of our country are being hurt because China is, for “negotiating” reasons only, not buying. We’ve made so much money on tariffs, that we are going to take a small portion of that money, and help our farmers. I will never let our farmers down!

This is perfectly fine, there’s nothing wrong with it. Trump Case is cool because it’s a character-level way of aiming for the same thing. So now we can see too that - like the parenthese, comma, semicolon - capitalization is not just a set of rules you can get wrong - “you must capitalize the first character of a sentence, as well as proper nouns” - but also a modifiable element that can be used to transmit different meanings by using different capitalization choices.

Emily Dickinson was another syntactical idiosyncratic. Dashes meant things to her that were quite unclear to others, and the first publishing of her work (which happened only after she died) removed most of the dashes, in favor of semicolons, commas, and periods. This first dash-impoverished version was prepared and published by two of her friends, and it is wonderful that they did so - if they hadn’t, likely none of us would have heard of Emily Dickinson. They gave us a wonderful gift.

But god, what butchery! The dashed versions - the one Dickinson intended - look like this one (original):

I shall know why — when Time is over —
And I have ceased to wonder why —
Christ will explain each separate anguish
In the fair schoolroom of the sky —

He will tell me what “Peter” promised —
And I — for wonder at his woe —
I shall forget the drop of Anguish
That scalds me now — that scalds me now!

But this poem in 1890 was published as:

I shall know why, when time is over,
And I have ceased to wonder why;
Christ will explain each separate anguish
In the fair schoolroom of the sky.

He will tell me what Peter promised,
And I, for wonder at his woe,
I shall forget the drop of anguish
That scalds me now, that scalds me now.

In the 1890 editing, the meter is off, the musicality badly damaged. (And even what I am calling the “original” is badly chained by the demands of Type. Dickinson wrote her poems by hand, and her dashes varied in length and in angle; Typographers have only a handful of dash characters to choose from).

But the musicality. If you don’t see it, try focusing only on the difference between

I shall know why, when time is over,
And I have ceased to wonder why;

and

I shall know why — when Time is over —
And I have ceased to wonder why —

Read them in your head, or say them aloud, and you see: these are different.

Incredibly - and I swear I did not know this, I am researching this essay as I write it, I did not know this, I literally wrote the entire section on Trump Case, then thought “what other examples can I give” and remembered Dickinson’s dashes, and went to her poems only to talk about the dashes — and yet — it may be that the only other prominent user of what I called “Trump Case” was ——— Emily Dickinson!

Look at the original poem again:

— when Time is over —
I shall forget the drop of Anguish

Time and Anguish get capitals - but schoolroom, sky, woe, these nouns do not. There is even an instance of lowercased anguish!:

Christ will explain each separate anguish

Thinking about it, it makes sense why “each separate anguish” deserves less emphasis - it refers to a broad category of anguishes that Christ is explaining in the schoolroom. The drop of Anguish, though - scalds her now. So even someone like you or I, who would rarely or never use capital letters in this way, can see that it makes more sense to capitalize the one she did, and why it would seem off to capitalize the first ‘anguish’, but not the second. There’s meaning there. The poem is different if you change it; the choices matter.^[2]

Lest you think I chose a particularly dash-y, capitalize-y poem — no. This stuff is primary Dickinson. I flipped to a random page in my 1960 collection (the Thomas Johnson edition, that aimed to render Dickinson more faithfully), and it looks like this.

Even for line breaks - things that basically just exist because the materials we write on and read from have finite width - the choice of where to put them carries meaning and feel. Edward Tufte, in his 2020 book, gives an example of two ways to write the words of Miles Davis:

Music is the space between the
notes. It’s not the notes you play. It’s
the notes you don’t play.

music is the space between the notes
it’s not the notes you play
it’s the notes you don’t play

Tufte makes a number of improvements in the second writing: italics work well here, lowercasing everything does too, but the critical change is the line breaks. Every time a line breaks just before a pause, it’s a tiny loss. Even in the sentence I wrote at the beginning of this section:

- the choice of where to put them carries meaning and
feel. Edward Tufte, in his 2020 book…

doesn’t work well! It should be

- the choice of where to put them carries meaning and feel.

Edward Tufte, in his 2020 book…

but some of you will read this on desktop and some will read it on mobile

so there’s nothing to be done.

I love how different these contrasting examples feel - the difference between No. and No!, the superiority of dashed Dickinson over edited Dickinson, the odd subtle shifts in meaning that occur when you write The Soybean Farmers of our Country instead of the normal-cased version; the line breaks. There is so much of this stuff. It is one of the main joys of writing, the mental cycling I do through all the ways I could write a sentence, the difficulty of settling on one, but also sometimes the feeling that the sentence I wrote could not be written in any other way without ruining it. Semicolons, commas, capitalizations, whether to use a dash, the length of that dash, it is all so rich.

Except for the quotation mark.

The quotation mark is a dead symbol. Inflexible and inert. It can be used in perhaps three ways:

• To quote or denote someone is speaking (the latter being more common in stories/novels/etc).
• To demarcate; for example earlier in this essay I wrote

I literally wrote the entire section on Trump Case, then thought “what other examples can I give” and remembered Dickinson’s dashes

In this use the quotation marks act like hyphens - it’s very similar to

I literally wrote the entire section on Trump Case, then thought — what other examples can I give? — and remembered Dickinson’s dashes.

another kind of demarcation was when I wrote

A comma is useful because a list like “Apple banana cherry” is wrong; the list “Apple, banana, cherry” looks better.

You couldn’t use hyphens to demarcate there. You could use line breaks, but using quotes keeps the sentence compact.

• To cast doubt or express disagreement on a claim^[3][4]:

The “true believers” say they’re better than us.

Last year’s “winner” is still very proud of himself.

The above usage types are useful, and I’m glad they exist. The issue is that there’s no interesting way to vary how the quotation mark is used. All the variance in how a quote or conversation feels, in text, is accomplished by the other punctuation marks. In this example fragment from the story Claw, one character is driving, the other is talking to them over the phone.

“Okay, Nathaniel,” Carson said. “I’m going to ask you some questions. Part of the reason is to keep you awake. You’re tired, it’s the evening, you’re on a straight road in the dark.”

“I can stay awake.”

Just a few changes to punctuation and font changes Carson’s tone from straightforward to confrontational:

“Okay, Nathaniel,” Carson said. “I’m going to ask you some questions. Part of the reason is to keep you awake. You’re tired! It’s the evening, you’re on a straight road, in the dark!”

There are lots of things like this you can change in any sentence, but the quotation marks are never one of them. It is just tragic that the “ can not be modified to carry any additional information beyond its bog-standard use. Even when a modification to the entire quoted line is desired:

“I can stay awake.”

This line is spoken over the phone, and the author wants to make it clearer this speaker is on the other end of a phone call. So he uses italics. Very reasonable choice - but it feels like something the quotation mark could, theoretically, could do, in a world different from ours. A “phone-quote” mark, perhaps, instead of a basic quote mark? ‘‘‘ instead of “? Maybe part of the issue is that it isn’t easy for the eye to see the extra ‘ in ‘‘‘. The eye can distinguish the . , ; triplets easily, but my eye stutters on counting how many ‘ there are in ‘‘‘‘‘.

But then we have to ask — why two ‘ marks, to make the quotation mark? A quotidian reason: when you only use one, it’s an apostrophe. We already had the mark that goes in “don’t”, in “I’m”, in “Maxwell’s”; so two ‘ were used to distinguish the quote mark from the existing apostrophe.

But… why choose a mark that needed to be distinguished from ‘ in the first place? Did we run out of shapes? We have a punctuation mark that’s just two already-existing ones in a row, really? Some other symbol entirely should have been used! It makes me wonder if quotation marks were a late invention, only thought up after the typewriter was invented, and society had already committed to a fixed set of characters.^[5]

The way that, to change the meaning in Carson’s sentence to Nathaniel above, every piece of punctuation except for quotation marks can be usefully varied, also suggests a situation where quotation marks arrived late to the English language: all the meaning-variation was already taken, so the quotemarks had to settle for a static and fixed role.

My favorite solution to this problem - that in a story, the standard rules of English demand you put these inert static marks everywhere, that catch the eye but always mean the same thing and are therefore uninteresting - my favorite solution to this is in the writing of Delicious Tacos:
 

Was I able to resolve your issue today, said customer service.

Absolutely, thank you. So I’m getting a credit for $36.75.

I’ll put that in the system sir yes. For the credit to be issued I have to put you on a brief hold. I’m going to send you over to the department that’s actually authorized for that.

Wait what-

I can put the credit in your file. But the credit has to be issued by the cancellation department-

But they’ll be able to see that I should get the credit, right?

They’ll have access to my notes yes.

How long will I be on hold-

Unfortunately I have no way of knowing that sir. I’m transferring you now-

WAIT, he said. But jazz music was playing. A trumpet ascending over Latin rhythms. Did you know that most billing questions can be answered online at Fulcrum dot com? Log in now to view your account, review billing details, and make payment arrangements.

He googled fulcrum cancellation department wait time reddit

“On hold over 1.5 hours twice for cancelation,”

I should let this go, he thought.

His solution is to rip them out, delete them all! They weren’t doing enough. He deigns to use them once, but for the title of a Reddit post. The standard version is not better:

“Was I able to resolve your issue today,” said customer service.

“Absolutely, thank you. So I’m getting a credit for $36.75.”

“I’ll put that in the system sir yes. For the credit to be issued I have to put you on a brief hold. I’m going to send you over to the department that’s actually authorized for that.”

“Wait what-”

“I can put the credit in your file. But the credit has to be issued by the cancellation department-”

“But they’ll be able to see that I should get the credit, right?”

“They’ll have access to my notes yes.”

“How long will I be on hold-”

Unfortunately I have no way of knowing that sir. I’m transferring you now-

“WAIT,” he said. But jazz music was playing. A trumpet ascending over Latin rhythms. Did you know that most billing questions can be answered online at Fulcrum dot com? Log in now to view your account, review billing details, and make payment arrangements.

He googled fulcrum cancellation department wait time reddit

“On hold over 1.5 hours twice for cancelation,”

I should let this go, he thought.

One objection that could be made here is, well, this is mostly rapid back-and-forth conversation, so the quotes can be dropped here; but in a text that has lots of description, with conversation interspersed, the quotes are necessary to distinguish the narrative description from the things the characters are saying. And perhaps that’s true, but once an author has used quotation marks for conversation in one place, they feel bound to use them everywhere. Claw is a book with tons of description, as well as plenty of conversation interspersed, but rapid back-and-forths exist there too:
 

“Okay, Nathaniel,” Carson said. “I’m going to ask you some questions. Part of the reason is to keep you awake. You’re tired, it’s the evening, you’re on a straight road in the dark.”

“I can stay awake.”

“I believe you. I still want to know. Do you have any identifying marks? Birthmark, tattoos?”

“Tattoos.”

“Army?”

“Yeah.”

“You have the option of getting that covered up. We can handle that, but it’s a process. We’d need you to follow very strict instructions.”

“No. I can wear a jacket.”

“Have you ever bitten anyone in the commission of a crime?”

“No. Who do you think I am?”

Confrontational. Mia took a note, aware Carson was watching her type.

Does this work without quotemarks?

Okay, Nathaniel, Carson said. I’m going to ask you some questions. Part of the reason is to keep you awake. You’re tired, it’s the evening, you’re on a straight road in the dark.

I can stay awake.

I believe you. I still want to know. Do you have any identifying marks? Birthmark, tattoos?

Tattoos.

Army?

Yeah.

You have the option of getting that covered up. We can handle that, but it’s a process. We’d need you to follow very strict instructions.

No. I can wear a jacket.

Have you ever bitten anyone in the commission of a crime?

No. Who do you think I am?

He was confrontational. Mia took a note, aware Carson was watching her type.

It doesn’t feel like it works. In particular, the final line where Mia takes a note is difficult to distinguish as being separate from the conversation. So getting rid of quotation marks means you then have to demark things-that-are-spoken from things-that-are-not-spoken in different ways. The top two ways are

1) phrases like “he said,” and

2) line breaks.

These two things alone go most of the way toward being able to get rid of the quotation mark in written conversation, and still keep things clear. The frustrating thing is that both are still usually necessary when using quotemarks! Read anything with quoted conversation: He saids are still all over the place, each character’s speech still gets its own line break. So even this very heavy punctuation mark - twice the size of an apostrophe - still requires clarifiers. Multiple redundancies just to make it clear someone is speaking. Perhaps this is just that difficult of a problem? Maybe clearly denoting who is speaking what is fundamentally difficult, and no system could solve it cleanly?

That a quote must be closed, even when nothing else is on the line, is also a bother. We are all so used to quotation marks by now that what I’m about to suggest offends the eye, and is not a real suggestion, but if a line is entirely quote, why use a symbol that must be closed later? Instead, just mark the line once at the beginning:

“Okay, Nathaniel,” Carson said. “I’m going to ask you some questions. Part of the reason is to keep you awake. You’re tired, it’s the evening, you’re on a straight road in the dark.”

>I can stay awake.

>I believe you. I still want to know. Do you have any identifying marks? Birthmark, tattoos?

>Tattoos.

>Army?

>Yeah.

>You have the option of getting that covered up. We can handle that, but it’s a process. We’d need you to follow very strict instructions.

>No. I can wear a jacket.

>Have you ever bitten anyone in the commission of a crime?

>No. Who do you think I am?

Confrontational. Mia took a note, aware Carson was watching her type.

The > is a little too large for this purpose, I’d like a lighter mark, but you see what I mean - the lines where nothing comes after the words being spoken do not need a closing “, where the lines that are mixed (“Okay, Nathaniel,” Carson said. “I’m going to ask you some questions) do.^[6] But the need to still use “ in some places means using a single-marker like > is not a clean solution either.

So I don’t know what to do. Perhaps there is nothing to be done. I only wanted to share my pain.

1. ^{^}

   A couple hours before I wrote this line, I mean. Not a couple hours ago for you.

2. ^{^}

   People understand Dickinson’s casing about as well as they understand Trump’s. The best the Emily Dickinson Museum’s website can do is

   She also capitalized interior words, not just words at the beginning of a line. Her reasons are not entirely clear.

   There have been arguments that there was no meaning to be found at all in Dickinson’s capitals; R.W. Franklin makes fun of people like me, who consider Dickinson’s capitals as carrying meaning, by pointing out a recipe she wrote down:

   If we follow John Crowe Ransom’s theory, the capitals are Emily’s “way of conferring dignity” upon the ingredients of Mrs. Carmichael’s cake, or are her “mythopoetic device” for pushing Butter, Flour, 6 Eggs, and a Cocoa Nut (grated) into “the fertile domain of myth.” At the same time, according to Charles R. Anderson, we are asked to use the punctuation here as “a new system of musical notation for reading” the recipe. Or, applying Miss Stamm’s theory, Emily Dickinson has not only got the recipe, but has indicated how one is to declaim it.

   [More in Denman 1993, Emily Dickinson’s Volcanic Punctuation]

3. ^{^}

   Not understanding this type of usage can cause issues - I have seen many an immigrant storefront advertising

   “Huge” sale!

4. ^{^}

   The cast-doubt usage of quotation marks have the distinction of being the only punctuation mark to have broken containment, jump off the page, and enter the language of oral communication: The air quote.

5. ^{^}

   
   You may say, well, a ; is just a . on top of a ,. But that’s perfect! because a ; is less of a stop than . but more of a stop than a , — whereas the “ symbol used for quoting has no such relation to the ‘ used for combining “do” and “not” into “don’t”.

6. ^{^}

   I don’t actually suggest the > for novels or anything, but it is already in use as a quotemark in some places. Here on LessWrong, on desktop, typing a > creates a quoted section (with the little left sidebar), but on mobile (for me), the > does nothing and just appears as a >. I still use in when quoting someone I’m speaking with, though, especially when disagreeing or arguing, because it’s safer than “.

   This is because the “ mark’s use as a quoter can conflict with its use as a “this is stupid” marker. Recall that a line like

   Last year’s “winner” is still very proud of himself.

   intentionally disrespects the subject. If I’m disagreeing with someone online, especially on a fraught topic like politics - for example if they say “The president’s choice of sandwich at McDonald’s is suboptimal” - if my responding comment is something like

   “The president’s choice of sandwich at McDonald’s is suboptimal”
   [disagreement, my argument]

   It can sometimes look like I’m using the quote marks to make my opponent sound stupid. But > does not have this connotation, so quoting them with > instead

   >The president’s choice of sandwich at McDonald’s is suboptimal
   [disagreement, my argument]

   is generally safer. No one has ever used a > in a sentence like “Last year’s >winner is still very proud of himself”, so there’s no possibility of confusion.