Unsymmetric Double Emdash

Question

In most cases, the emdash is used symmetrically to add Parenthetical Details.

It can also be used unsymmetrically to add Details at the end of a sentence.

[[ EDITORIAL COMMENT :

This Question is about "2 Single Emdashes" Versus "1 Double Emdash" ; It is not about the spacing around the Emdash ; It is common not to use spaces , but it is Possible to use spaces according to some Style Guides.

Eg 1 :

Most grammar resources and style guides advise not to put any spaces before or after an em dash [....] other style guides and many newspapers will often put a single space before and after an em dash

Eg 2 :

The em dash is typically used without spaces on either side, [....] Most newspapers, however, set the em dash off with a single space on each side.

I have included Examples with and without spaces. The Crux of this Post is the quote by Jimmy Wales, not my Examples.

Here is this Grammarly Article which might be relevant :
https://www.grammarly.com/blog/why-you-should-love-the-em-dash/

END COMMENT ]]

Symmetrically Parsed Example:

It turned out that the three sisters ( Alexa, Siri, and Cortana ) were actually robots.
It turned out that the three sisters — Alexa, Siri, and Cortana — were actually robots.
When I gave away the oxen (all 8 of them) I had more time to travel.
When I gave away the oxen—all 8 of them—I had more time to travel.

Unsymmetrically Parsed Example:

The winner was the last : Cortana.
The winner was the last — Cortana.
The verdict was shocking : Guilty !
The verdict was shocking—Guilty !

Now, confusion arises when these two uses get mixed up in the same sentence.

I've joked many times — it may not be a great business model to give things away and hope people will voluntarily support them — but this is how I've built my career so far!
SOURCE (including the spaces) :
https://tech.slashdot.org/story/22/07/09/0129230/jimmy-wales-solicits-donations-for-his-ad-free-social-network

Problem : It looks like the Symmetric use, but it is actually the Double use of the Unsymmetric use !
It can be interpreted in both ways !

Symmetrical Interpretation:

I've joked many times [that] "It may not be a great business model to give things away and hope people will voluntarily support them" but this is how I've built my career so far!

Meaning : Jimmy has built the career by joking many times ! The Joke is not all that funny !

Unsymmetrical Interpretation:

I've joked many times — "It may not be a great business model to give things away and hope people will voluntarily support them — but this is how I've built my career so far!"

Meaning : Jimmy has joked many times ! The joke is still not all that funny !

Questions:
(1) Is my thinking correct or valid ?
(2) In general, is there a way to remove the ambiguity without using more Punctuation like Parenthesis or Quotes ? Eg: By varying the size of the Dashes or the Spacing ? In a nutshell, can we indicate that Double emdashes in sentence are either indeed Symmetrical or indeed unsymmetrical ? Or is it inherently ambiguous ?

Answer 1

(1) Is my thinking correct or valid ?

You are incorrect. Your example of "unsymmetrical" dashes is actually a normal use of paired (symmetrical) dashes. Consider this:

The winner—Cortana—was the last.

The paired dashes surround a removable appositive. Your example instead attaches the appositive to "the last", so the second dash is removed because that is the standard practice before terminal punctuation:

The winner was the last—Cortana.

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(2) In general, is there a way to remove the ambiguity without using more Punctuation like Parenthesis or Quotes ? Eg: By varying the size of the Dashes or the Spacing ? In a nutshell, can we indicate that Double emdashes in sentence are either indeed Symmetrical or indeed unsymmetrical ? Or is it inherently ambiguous ?

There is really no ambiguity. The Slashdot example that you cited is a bit unusual because the first dash is used in a somewhat atypical way. If I were editing that sentence and trying to adhere to convention, then I'd probably replace it with the subordinator "that" (as you suggest).

The second dash is used to "set off" a conjunct.¹ A comma would normally appear there, but a comma is, of course, typically deleted when a dash arrives.

Therefore, more typical punctuation would be:

I've joked many times that it may not be a great business model to give things away and hope people will voluntarily support them, but this is how I've built my career so far!²

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¹ When we have two conjuncts, the second (along with the coordinating conjunction) may be surrounded by paired punctuation. That is actually what is happening here. The second dash, as before, is omitted because it immediately precedes the terminal punctuation.

² Some people (including me) would prefer to omit the comma if everything following "that" were considered part of that subordinate clause. Here I'm considering the entire sentence to consist of two main clauses separated by ", but".

Answer 2

I respectfully think your examples of asymmetrical usage are incorrect, and native speakers would not normally write them. In particular,

The winner was the last : Cortana.

There is no space preceding a colon in English, unlike French.

The winner was the last — Cortana.

This would often be read, in standard written English, as an attribution of the preceding sentence to Cortana. For example,

“I know not with what weapons World War III will be fought, but World War IV will be fought with sticks and stones.”

― Albert Einstein

Em dashes are normally used within a sentence to introduce parenthetical phrases. When you use em dashes this way, the parenthetical is more emphasized than if you had set it off with commas, and even more emphasized than if you had used parentheses. Grammatically, it’s similar to if you had written,

The winner was the last (Cortana).

However, using parentheses implies that the identity of the winner is the least important part of the sentence, whereas if you had written,

The winner—Cortana—was the last.

This emphasizes the fact that it is Cortana as especially important.

Some writers, most famously Emily Dickinson, use an em dash to represent a pause in speech, and not according to rules of formal grammar. Kurt Vonnegut argued that writers should do this and avoid the ellipsis, which originally meant that some words are being skipped.

So, using an em dash to introduce a final phrase, giving it extra emphasis both through punctuation and position, can be an effective technique. However, be careful to avoid ambiguity with the other possible meanings of an em dash, particularly for attribution and to mark a change in who is speaking.

This particular example is not, as you say, well-written:

I've joked many times — it may not be a great business model to give things away and hope people will voluntarily support them — but this is how I've built my career so far!

In this case, the sentence is grammatically incorrect because the sentence with the clause set off by dashes removed makes no sense: “I’ve joked many times ... but this is how I’ve built my career so far!” He did not build his career despite joking many times.

So, what I think is going on is that the writer is using dashes informally to represent any kind of pause. This usually works. We can understand spoken English without punctuation marks, after all. But sometimes it becomes confusing or overly informal. I think one possible way to punctuate this better would be:

I've joked many times: It may not be a great business model to give things away and hope people will voluntarily support them, but this is how I've built my career so far!

Or you could still use an em dash before the clause starting with “but,” so long as you remove the confusing first one.

Answer 3

If you use double dashes for punctuation (British: spaced em dashes, US: tight double em dashes) this is generally an alternative to commas. Some authors never use them. I probably over-use them, but find a justification in long sentences which already contain commas.

The purpose of punctuation is to aid in the correct reading of a sentence. If double dashes clash with single dashes, replace the former by commas (this is a change, not an addition) or, in cases, the latter by a colon.

But no, there aren’t any standard alternatives, and the poster is already indulging himself in using a non-standard space before a colon. That died in English typesetting about fifty years ago.