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This is going to be an unfair comment.

Today marks the first occasion that I saw the title of a post on HN, then saw that it came from Medium, and on the basis of its domain name decided that it would probably be a fluffy and superficial treatment of the topic alluded to in the title, where typography (ironically enough) and a very generous x-height gave the impression of substance to something that was in point of fact really barely worth writing or reading in the first place.

Having noticed this thought arise, I decided I better go through to read the article and see if I was right.

This article reads like a piece from a content farm. I flagged it and going forward the urge to flag everything from Medium will be hard to resist.
Writing 'twenty eight' as 'twenty-eight' is accepted practice? The looks very odd to me. But perhaps that's a difference between British and American forms.

Also 'friendly-looking' isn't joining together two adjectives , it's making a compound adjective.

It makes sense, as it would remove the ambiguity of something like "Those are twenty eight year olds." Am I referring to 20 children, or some number of adults?
Yes, "twenty-eight" is the preferred form in the UK.
Looked fairly normal to me. US here.
If nothing else, that's how I learned to write out the number in words on a check (in the USA).
I'll never understand typesetting fans. Two spaces after a decimal point is confusing and incorrect (even though it has the advantage of using buttons that are actually on the keyboard) whereas having three different kinds of dash that are identical except for width (the middle one being generally indistinguishable to the layperson's eye) is perfectly sensible.
In HN style I'm going to comment by bashing a very minor detail of the article: at my current page width the subtitle: "Below I cover the common uses of three horizontal marks: the hyphen -, the en dash –, and the em dash —." breaks lines so that a new line starts with a comma and that's very bad!
Here's more on dashes and hyphens: http://practicaltypography.com/hyphens-and-dashes.html
Using the hyphen in "friendly-looking" is incorrect. The exception for hyphens in compound adjectives is when the first adjective ends in "ly." It should be "friendly looking couch."

http://www.grammar.com/compound-adjectives/

"Friendly-looking" is correct (if a bit archaic), as "friendly" is an adjective, not an adverb.

Most "-ly" descriptors are adverbs, and it is indeed incorrect to compound "-ly" adverb-adjective combinations with a hyphen. (For example, "finely-chopped garlic" is incorrect). But adjectives that end in "-ly" can be hyphenated. ("Friendly," "elderly," "dastardly," "squirrelly," "burly," "lovely," "ghastly," "deadly," and so on).

These days writers often choose not to hyphenate them, as compound-hyphenation in general is dying out in contemporary usage. It often feels old-fashioned and fussy in informal writing. But there is no rule prohibiting the compound-hyphenation of adjectives with "-ly" endings.

Thanks for the corrections! :)
No worries. I dig the username, btw. :)
Most hyphenation in compound adjectives occurs when the compound adjective comes before the noun, that is, in the attributive position. As a broad rule, when a compound adjective appears after the noun it modifies, that is, in the predicative position, it will not be hyphenated.

That is so arbitrary. Your source and the OP's source are linguistically prescriptive. Prescriptivism is unscientific and it leads to endless spats between groups of people that think the way they learned to speak and write is somehow superior. A better approach is to look at the reality of how native speakers of a language use, pronounce, and write words (descriptivism) and agree that some uses are standard, and some are non-standard.

Here are some screenshots of collocation searches involving post-adjectival 'looking' from the excellent COCA...

'good':

http://s9.postimg.org/r4cok4spb/good_looking.png

'nice':

http://s9.postimg.org/kcm9ha3pr/nice_looking.png

Here's one for your author's example, "well known" (or "well-known"):

http://s9.postimg.org/64wksmr0v/well_known.png

Notice that the reality bears almost no resemblance to the prescriptive idea of what's correct and incorrect.

No, if you read your own link, the exception identified is for adverbs that end in "-ly" that are part of a compound adjective. "Friendly", though it ends in "-ly", is an adjective, not an adverb.

The "Friendly-looking" in "Friendly-looking couch" is an "adjective + participle" construction, which is hyphenated before the noun.

http://www.chicagomanualofstyle.org/16/images/ch07_tab01.pdf

That rule applies to adverbs. The distinction is admittedly subtle, but this page lists the exception you cited (in rule 5), but also uses "friendly-looking" in an example (in rule 4):

http://www.grammarbook.com/punctuation/hyphens.asp

Is it common to use "she" for punctuation marks? Or is it a perversion of the current trend in mixing he and she randomly?

Oh, and is "looking" really an adjective? It must be: this author is lecturing us about English usage, I can't believe she wouldn't tell adjectives and verbs apart.

The point is if you left the hyphen out, looking could be interpreted as an adjective, and therefore there must be a hyphen between friendly and looking.
> Oh, and is "looking" really an adjective?

Among other things.

"looking" is a actually a present participle; this form functions as a part of a compound verb used in forming continuous tenses, as a noun, and as an adjective.

http://en.wiktionary.org/wiki/present_participle

This thread is way off the front page so maybe you won't see this but I thought you might find it interesting.

'look', when not part of any phrasal verb ('look at', 'look for'), is actually a copula in English. A copula is a linking verb, the paradigmatic example being 'to be', that can occur in the pattern (subject) (copula) (adjective).

That's what is happening in sentences like

"The man (subj) looks nice (adj.)"

Whereas with any noncopulative verb we need an adverb

"The man ran quickly.", "The stocks fell rapidly.", etc.

http://en.wikipedia.org/wiki/List_of_English_copulae

What's interesting is that if you look at the list of English copulae above, you'll notice that many of them ('smell', 'sound', 'feel', 'taste', and 'seem') are capable of the same kind of inversion as 'look' in their participle forms. So...

"The chicken tasted funny." and "The chicken is funny tasting."

"This song sounds sad." and "This song is sad sounding."

It's a little more awkward to think of examples with 'seem', which is curious since it's the only one of those six copulae mentioned that isn't sensory in meaning.

TL;DR: 'looking' is definitely not a standard adjectival participle, since it can't function as an adjective on it's own, but instead needs to follow another adjective. Another excellent example of how words do not conform neatly to part of speech categories.

Ok, then looking is not an adjective, it forms an adjective compound with another adjective.
Correct, a member of the same small POS group as 'smelling', 'feeling', 'sounding', 'tasting', and 'seeming'.
The problem for me is remembering how to create the various dashes on a typical keyboard.
I type Ctrl+Shift+U 2014 Space (U+2014 EM DASH) surprisingly regularly. (That's with Ubuntu.) U+2013 is EN DASH and U+2010 is HYPHEN.

Does anyone else find that they know dozens of Unicode code points purely by accident? Other useful ones in that block are U+2018, U+2019, U+201C and U+201D, the left and right (first and third) single and double quotation marks...

In the end, though, I really wish everything supported Vim's digraphs. (e.g. Ctrl+K l * produces λ.) I know even more of those than I know numeric codepoints…

I find using the compose key easier than remembering Unicode points. For em dash: `Compose - - -`, for en dash: `Compose - - .`.
Didn't know about C+S+U - thanks!
Macs are great for this. Option-hyphen gives you an en-dash and option-shift-hyphen gives you an em-dash.
The linked Wikipiedia article has some shortcuts further down: http://en.wikipedia.org/wiki/Dash#Rendering_dashes_on_comput...
That's was I was wondering. How do I write an Em dash on a keyboard? I've always just used a hyphen for this (but I'd like to do it right).
I have used MS's Keyboard Layout Creator to add those — and many others — to my keyboard. Right-alt-minus for en–dash and shift-right-alt-minus for em—dash.

What I really want is for my keyboard to act like my mobile phone keyboard — a long press to see similar characters. Anybody care to code it?

Custom layouts FTW. I have the following line in my layout configuration (Linux/xkb):

    key <AE11> { [  minus,          underscore,     endash,         emdash          ] };
That's what my Macbook does. It actually drives me crazy because you lose key repeat. You have to furiously mash keys in vim, no holding them down.
Macs do that??? I'm surprised that I never discovered it on the wife's Mac. I deal with other languages so much, this might be the one thing that tips me toward using one.

    defaults write -g ApplePressAndHoldEnabled -bool false
It should be easy to use a meta key to specify you want a menu. I wonder if anyone's made the option.
While I think that proper em dash usage—like this—looks fantastic, I'd be happy enough if somebody just ran s/ - /--/g on the internet.
Note that different style manuals will suggest em-dashes set closed for that use or en-dashes set open; either is better than hyphens (open or closed).
Oh bother. Use `-` for hyphen and `--` for dash. That's it and that's all you need. If a style transformer wants to convert `--` to &ndash; or &mdash;, fine whatever. But f* the difference between the two.

Please, stop making things more more complicated than they need to be! It is so f*ing tiresome.

My character set has 7 bits -- and that's the way I like it.
What was that green bar flashing across the top of the screen while I was trying to read the article?
And what symbol is used for the "minus" operator?
Ah, for minus you should probably use &minus; (U+2212), which will typically display at the same width as numerical figures.

Next question: should you use the same character for unary minus and binary minus? That is, to represent negative numbers and subtraction? ;)

This leaves out hyphens at line breaks for long words.