“Capturing the zing of conversation requires attentive listening and painstaking revision.
It comes from connection,
from the narrator subtly reaching out to the reader and saying, ‘We’re in this together.’”

Sin and Syntax: How to Craft Wicked Good Prose, by Constance Hale, is one of those rare grammar guides you can take pleasure in reading front to back because it’s so engaging, witty, and illuminating.

I own plenty of grammar manuals, but this is a far more inspiring creature that goes beyond just the rules. It teaches not only how the cogs and inner devices of sentences work, but how they can be fitted together to create beauty, suspense, and drama.

“Phrases can build grace into sentences. Taut declarations lend clarity, but too many of them can start to sound like a Dick-and-Jane story. A strategically placed phrase can turn a staccato burst into a more lyrical sentence. This is what we mean by ‘turning a phrase’ — using our command of language and mastery of the rhythms of a sentence to affect style as well as substance.”

Just like with everything else, it takes a lyricist to reveal the Truth: metaphors just fit better into the human mind.

For example, compare these definitions from the Chicago Manual of Style (AKA the “editor’s bible”) with those from Sin and Syntax (the self-described “hip bible and essential covenant for crafting stylish prose”). This is not to say the CMS is bad; I couldn’t be without it — but it has a different purpose. It’s an operating manual for editors, whereas S&S is an ode to grammar for writers and readers too.


“A pronoun is a word used as a substitute for a noun or, sometimes, another pronoun.” (CMS)

“Pronouns are proxies for nouns. They stand in willingly when nouns don’t want to hang around sounding repetitive.” (S&S)


“An adjective is a word that modifies a noun or pronoun; it is often called a “describing word.” An adjective tells you what sort, how many, how large or small, whose, and so on.” (CMS)

“Adjectives are consorts, never attending a party alone, preferring to hook themselves on the arm of a sturdy noun. Adjectives embellish their companions, defining the qualities of the person, place, or thing they’re escorting, and sharing relevant details whenever possible.” (SMS)


“A verb denotes the performance or occurrence of an action or the existence of a condition or a state of being, such as an emotion. … The verb is the most essential part of speech—the only one that can express a thought by itself (with the subject understood).” (CMS)

“[Verbs] add drama to a random grouping of other words, producing an event, a happening, a moment to remember. And they kick-start sentences: without them, words would simply cluster together in suspended animation, waiting for something to click.” (S&S)

Sin and Syntax is divided into three parts: WORDS, SENTENCES, and MUSIC. The first two parts deal with the anatomy of language, while the last part unravels the secrets of melody, rhythm, and in a writer’s voice.

I love that Hale uses examples from how humans actually speak in Modern Day as well as well as the more traditional prose of the past, which is what many of the more prescriptive grammar books concentrate on. Hale happily uses examples from everything from the Bible to WIRED magazine and Twitter posts to illustrate the playfulness of how we use words. She doesn’t shun traditional grammar at all, but incorporates everything to give a wider-than-usual view.

There are some great passages on editing and revising too. She did a lot of research to find out how writers actually hone their manuscripts; for example, she pored over Mark Twain’s draft manuscripts preserved in a library to analyse which words he crossed out and what he replaced them with, and then explained why he might have made these choices.

Since I read Sin and Syntax, I’ve been enjoying reading a lot more and just listening to people talk too; it’s helped me appreciate even more deeply why people say what they do and the alchemy of language. I highly recommend this book not just for editors and writers, but for readers too… and anyone who loves the art of conversation. Basically, humans should own this book.