Crib Ross Gay's Conversational Style

Last week during “Drop-In Tuesday”, we read Ross Gay’s “Tomato on Board” from his bestselling flash essay collection, “Book of Delights.” For an entire year, everyday Ross wrote down one thing that delighted him. Those delights became this book (and a second book, “The Book of More Delights”).

You can read the essay for free on the publisher’s website or let Ross read it to you! Or why not both? He’s very charming, so if you’ve not attended a reading, I highly recommend watching the Youtube recording of his reading from seven years at Algonquin Books.

During the workshop, I gave quickie lectures on three things:

For today’s newsletter, I want to share the last one (What about the other two?! Well, sometimes you just gotta be there — see you Tuesday…?).

There’s so much talk right now about AI’s writing style, but even before that janky robot writing voice came onto the scene, many people were beginning to adopt a marketing bro voice (as someone who’s done quite a bit of ghostwriting for startup founders, even I’ve been guilty of it!) or a bloggy girlypop style of writing (As someone who’s chronically online — ALSO GUILTY).

There’s nothing inherently wrong with either of these voices, if that’s your audience. But what I suspect is that most people have a desire to cast off the stilted Academic-lite voices they developed during undergrad to get through college and are justing reaching for the most prevalent, casual writing style they can to use it as a model for developing their own voice.

But, might I suggest Ross Gay as your model for a conversational writing style?

These are not hard and fast rules and you are not beholden to doing any of these things in your writing for it to be “good.” All this is is what Ross Gay does — or rather, what I think Ross Gay is doing — to write in a more conversational style.

You can try any of these tips out. Keep what works. Toss what doesn’t.

Before you read the rest of this newsletter, you’re probably going to want to pause real quick and read “Tomato on Board” first. Don’t worry, it’s super short.

If you’ve had any formal writing education, you’ve probably had it beat into you that run-on sentences are BAD. But ever since I was a kid, I’ve been enamored by lengthy, exuberant sentences that almost leave you breathless by the end of them.

Sure, there’s an argument to be made for writing sparse, bare, clipped sentences. I do a bit of that too. But what I don’t think is defensible, is teaching people an entire style of sentence is completely off limits!

What’s key to writing a strong sentence — whether it be short or long — is control. Your sentence should never read as if, you the writer have not chosen each word in that sentence with intention.

(Unless the effect you’re trying to create is uncontrolled runaway sentences, but that’s a discussion that belongs in a craft essay on writing nonfiction at the meta level, not this newsletter lol. Let’s stay focused.)

As a poet, Ross is a master of word choice and precision. Just because this essay reads like he’s telling a charming story at a sidewalk cafe with friends over espressos, does not mean that’s how it was written (or rewritten and revised and revised to perfection).

Let’s take a look at the first page. The first sentence is quite lengthy, then there’s a short lil’ three word sentence, followed by another lengthy sentence. The remaining sentences on the first page are also fairly lengthy.

The length of the sentences is what keeps the essay flowing along. The control applied to the writing of the sentence is what keeps a long sentence from getting bloated or clunky. The short little sentence puts emphasis on baby (which will be an ongoing motif throughout the essay) and it serves as a rest stop before you pull back into the frenetic pace of this essay.

The other thing that an effective long sentence does is that it doles out the information in the sentence as you need it. If someone has to read to the end of your sentence for the information that’s going to make the first part of the sentence make sense, you’ve written a confusing, convoluted sentence and this slows the flow of the reading because your reader has to keep stopping and rereading sentences once they have all the info so the sentence makes sense.

Think of it like a recipe being written out of order. You can’t get through the meal prep without constantly having to revisit previous steps and your stew burns. The recipe writer also doesn’t give you too much info upfront because they don’t want to overwhelm you. They mete out the information in a thoughtful manner, giving it to you as you need it and in an order that makes sense. Each bit of information builds on the last bit of information. Your sentences should be structured similarly.

This is honestly one of the most important things I’ve ever learned about writing clean, crisp sentences of any lengths. It’s a bit of info I pass along frequently to writers I’ve edited. But also it’s something I hate talking about because my understanding and knowledge of syntax terms is shaky.

But in one of the first courses of my MFA, the professor assigned Virginia Tufte’s “Artful Sentences: Syntax as Style.” (It’s not available on Bookshop!) I knew the book was going to be dry based on the cover alone. I couldn’t get through a single chapter without dosing off.

I couldn’t even tell you what the proper term for this is because I don’t remember and I didn’t underline a single thing in this book. But I know I learned it from Tufte and I can remember my professor touching on it in class.

In an effort to be the best version of myself, I pulled Tufte off my shelf and flipped through it. It would appear this bit of helpful knowledge appears in Chapter 9 “Free Modifiers: Branching Sentences.”

LLMs being pattern recognition machines but not having a grasp of “segmented patterns” BECAUSE AI ISN’T HUMAN is also part of why AI writing sounds like it does.

And when you write with awareness of segmented patterns your sentences tend to be stronger and your essays will make more sense at the line level.

Ross also uses a lot of repetition in this work. Repetition has sonic value and it also keeps the essay rolling along quickly. Let’s look at the first page a second time, but this time to clock the repetition.

The difference between repetition and redundancy is that (usually) one is done with intention and the other is the result of sloppy writing. Because of the frequency of the repetition — and the fact that it sounds pleasing to the ear (redundancy tends to sound clunky) — it’s clear that repeating these words over and over were an intentional choice by the writer.

People tend to repeat theirselves a lot when we’re speaking. And while just straight up transcribing speech or trying to imitate that vocal tic will likely not create a pleasing or desired effect, you can make something feel more human, more like verbal storytelling and more casual by using intentional repetition.

The frequent repetition of tomato, baby and carry are also Ross subtly braiding these three things together in the reader’s mind, so the end of this very short essay feels like the natural cumulation of this idea that all three are related and makes that last line very satisfying.

On that first page, as Ross is traveling through the airport with his tomato seedling, he encounters a security guy who says,

“I don’t know how to check that. Have a good day.”

Okay, so stay with me, because this is going to be a little weird. But yes, when we speak, we tend to repeat ourselves and double back on ideas and just kind of vomit out these long, uncontrolled sentences. But when writing dialogue, dialogue tends to sounds “more real” and authentic when we use short, clipped sentences. Especially in brief, conversations had in passing, like this one.

I don’t know why this is. Someone smarter than me who probably knows all the syntax terms and shit could likely break it down for you, but alas that’s not me. Are there exceptions to this rule? Absolutely, because this isn’t a rule. It’s just an observation and there will be instances where it makes total sense for the effect you’re trying to pull off to give a character long wordy dialogue.

In this instance, Ross is writing a flash essay. The essay moves at a quick clip. And it’s also got a kind of wholesomeness to it and is humorous. To reinforce those facets of the essay, the dialogue is short and humorous as well and briefly — very briefly, so we don’t get waylaid as readers — inserts other voices into the essay. And because the dialogue tends to be short, it also functions as a little reader rest stop, like the three-word sentence I pointed out from page one.

The dialogue is serving the essay on multiple levels. Now, don’t panic. All of this doesn’t happen on the first draft of an essay. It’s choices you layer in during the revision process to level up your writing. (Level up? See, I told you I go all marketing bro sometimes).

Writing in a conversational style creates a feeling of familiarity between the reader and the writer (which is why so much online writing and marketing is done in an accessible, conversational way).

Ross creates this feeling of familiarity in a couple different ways in this essay.

He’s using language like “li’l guy” (the pros call that move personification) and at the end of the essay when referring to the childhood family car he refers to it as “that car” as if there’s understanding between him and reader as which car he’s speaking about (the family car is written about in an earlier essay in the book).

Ross uses ample asides during this brief essay, which imitates the digression we take when telling a friend a story, but he’s mimicking it in a more controlled manner. Sometimes the asides appear between dashes like “—not comparing a tomato to a baby, but carrying the tomato onto the plane—” or is info that’s not-but-is necessary like the fact that the plant came from his friend Michael and Michael smirked a the idea of Ross getting that plant onto his flight.