Why I Started Writing Crossword Puzzles

I wasn’t good enough to solve in pen—I’m still barely good enough to solve in pencil—but in the summer of 2019, I started doing the New York Times daily crossword puzzle. I’d strip the puzzle section from the office newspaper in the morning and keep it at my desk all day, peeking at it during long phone meetings. During a mundane workday, the satisfaction of puzzle solving was irresistible.

It took me a while to finally solve a puzzle. At first, I even struggled with the Monday puzzles—the easiest in the week. As I started reading clues, I realized I had never heard of common clues like ALEE (the side of the ship sheltered from the wind) or the Eugene O’Neill play ANNA Christie (embarrassing, since at the time I was working at a theater). Even though I was unable to complete them without a couple of hints, I immediately understood the appeal of a crossword. The puzzle had a beginning and an end, and you either got it or you didn’t. If you did, it chimed. Rarely are we given a problem with a solution that can be literally spelled out. My rat brain was listless and in search of a quantifiable reward.

It became an obsession. I’d try to think through gaps I’d left in the puzzle at my desk. If I was reading and stumbled on a peculiar word or piece of trivia, I’d wonder how it could be incorporated into a puzzle. I started an Excel sheet to store possible answers, sorted by length. Most of them I wouldn’t ever use, but I imagined SLEEPERCELL and BEDROOMPOP, tied together by SHUTEYE as the reveal for a slumber-related puzzle. I was dreaming in tiny black and white boxes.

*

In 2019, I had very little interest in writing publically, despite being extremely jealous of anyone who described themselves as a writer. I had kept a journal on and off, had experimented with writing a summer newsletter to friends, but still, writing terrified me. I had just left my first job in the book industry and had seen the depths of bad prose in the slush pile. I’d watched my coworkers bicker in endless email chains, sniping at each other over comma placement and em dashes on the company’s blog. I did not have the confidence to get torn apart in Track Changes and wanted no part of it.

And most importantly, I had internalized the message a lot of women and women of color receive when they express interest in writing: Our words are not universal. No one is interested in our writing. What we’re often asked for instead is stories about our pain or our trauma, and I had no interest in narrating the tragedy of my mixed Blackness. What I wanted to write was criticism about film and fiction, but I didn’t know who would want to read it.

 I was dreaming in tiny black and white boxes. 

So instead of writing what I wanted to write, I turned to crosswords. My fascination had morphed into a curious admiration: I didn’t just want to solve them; I wanted to untangle how they were created. I had to understand how it was possible that someone could ever make something so brilliant, and so I started trying to make my own.

To me, a crossword puzzle is one of the most elegant forms of writing, as mathematical as it is artistic. It’s not just about the beauty of a word in meaning or in appearance; it’s about its length, where in the word the vowels sit, how the word can interlock with another. Not just language, but logic. Looking at a truly perfect block of a crossword, where the clues are snappy and the fill is unforced, is like looking at a honeycomb or a four-leaf clover. It’s so satisfying, it seems impossible that it could have ever been created by something and not just dropped, flawless from its inception, into the world.

I immediately loved the playfulness of the crossword, how it seemed divorced from the strictness and formality of language that I had started to fear working in publishing. I had forgotten how malleable English could be, that there was not one inherently correct way to write and express something, that there could be style even in the shortest phrases. A great crossword clue was simultaneously coherent and bewildering. Like the best writing, crosswords embraced misdirection and the unexpected. “Summons before congress:” BOOTYCALL. “Digital art:” FINGERPAINTING. “Function with no limits:” ORGY. When I stumbled on one of these clues I was annoyed before I laughed. This type of wordplay was what had first enticed me about language when I started reading as a kid, and it was what I missed as an adult. The more crosswords I solved, the more interested I became in their complicated syntax.

*

I initially didn’t think much of seeing ENID Blyton appear frequently in the puzzle. She is a writer I only knew by name; I knew she wrote children’s books and mysteries. I did not know she has been repeatedly criticized, throughout her lifetime and after, for her deeply racist portrayals of Black children. When I say deeply racist, I mean she straight-up named one of the Black characters the N-word. Reading this, and realizing how many times I’d happily filled out her name, made me feel a little sick.

Blyton is perhaps the most common ENID you’ll find in a crossword puzzle. I’ve seen Blyton many more times than hints that reference the city in Oklahoma or the minor woman in Arthurian legend. But should she be? Do we continue to memorialize her in the puzzle just because her name is convenient, and if we do, do we need to indicate something more than a banal clue like “children’s author Blyton?”

For very good reason, I did not grow up with Blyton’s books, but seeing her so frequently made me question if the crossword expected its readers to have more than a passing familiarity with her name. It would be foolish to say that inclusion in the crossword is an endorsement, but it is an acknowledgment of someone’s relative cultural importance. Was I taking it too personally? And if I was going to make my own puzzles, was I going to include her?

An increasing number of crossword enthusiasts, both solvers and writers, have talked about the secret bigotry in the crossword. Much like the blank spaces in an unsolved puzzle, crossword writers and editors are pretty white. While there are plenty of other newspapers that publish popular daily or weekly puzzles, like The New Yorker or The Wall Street Journal, which intentionally cultivate a distinct tone from the Times, they have a similar audience and constructor base. That same overwhelming white maleness is reflected in the puzzles. At times, this means clues and answers are simply unnecessarily obscure to those outside that demographic of baby boomers; at others, they’re outright offensive and use archaic and racist terms.

The very concept of the crossword relies on the belief that there is a body of common knowledge that most people will or should know. A Monday puzzle in The New York Times assumes that most of the people solving it will know most of the answers, and the difficulty and obscurity of the clues increases each day. But who decides what’s common knowledge? Crosswords, especially the New York Times crossword, which has a subscriber base of half a million people, have a hand in standardizing what we remember and what we forget.

What does it mean to appear, repeatedly, in The New York Times—if only as trivia? I know what the EDSEL is, a short-lived and unsuccessful Ford car, because it appears in crosswords—and it only appears in crosswords because, structurally, it’s a useful word: two Es, ends in an L. The ALOU brothers were the first all-brother outfield in Major League Baseball, an interesting fact that few would argue is essential information—but they regularly appear in crosswords. I’m sure there are plenty of other baseball players who are more significant that I’ve never heard of because their names aren’t three-quarters vowel. Never mind that their home country of the Dominican Republic remembers them as the Rojas brothers, and it’s only because baseball managers didn’t understand matronyms that we know them as the Alous. And because L is a more useful letter than J, and ALOU is a more structurally useful fill than ROJAS, the New York Times crossword continues to call them the ALOUs. Which means other crosswords and puzzle makers call them the ALOUs, and now it’s just necessary to remember Matty, Felipe, and Jesús Alou if you want to solve the puzzle.

Maybe this common-knowledge question is why it wasn’t until 2019 that I became interested in crosswords. I remember watching adults do the puzzle as a kid and wondering how anyone could remember this much about old television shows and dead senators. I continued to assume I didn’t have the right knowledge and therefore wasn’t smart enough to solve them until I actually started trying.

But crossword puzzles are not a measure of intelligence; they’re an exercise. Solving a crossword does not mean anything other than that you can solve that crossword. It’s not important to the crossword that you know where ALOE grows or are familiar with the taste of an ACAI berry, but if you’re going to solve the puzzle you should know these words were used at least twenty times in the New York Times crossword just in 2021. This is how the body of common knowledge is created and established. Clues and fill get reused constantly, and there’s a reason. They work. You need words like ALOE and ACAI to prop up longer, more interesting fill—there’s only so many common words in the English language that are this vowel heavy. The question of common knowledge reenters when deciding what clue will be used to identify a fill.

But who decides what’s common knowledge? 

Take ARI, another extremely popular answer. I got so used to seeing “Shapiro of NPR” or “Grande, to fans” or even “Cardinals on the scoreboard” that I would fill this clue out without even thinking. But I started to wonder why I saw Ari Shapiro so much and not, say, Grammy-nominated R&B singer Ari Lennox or actress Nicole Ari Parker. One set of clues is mainstream, the other is niche—and unsurprisingly, it’s the body of knowledge that’s often associated with whiteness and wealth that’s reflected in The New York Times. Now that Nicole Ari Parker is in the Sex and the City reboot And Just Like That . . . , will she start showing up more on Mondays and Tuesdays than she did when she was on Empire? When I started making puzzles and found ARI slotted nicely into a line, who was I going to pick? But I’m never going to remember that there’s not just a baseball team called the Cardinals but also a football team, and so I had to go in a different direction when it came to my own construction.

I had plenty of other crossword puzzle makers outside of The New York Times to serve as role models. The Inkubator, a subscription service that publishes puzzles by nonbinary and female constructors, is one of the most popular homes for high-quality puzzles. Crosshare is a free, user-generated community of puzzle makers with a weekly newsletter guest-written by users who share their favorite puzzles. Blogs like Rex Parker Does the NYTimes Crossword Puzzle or Crossword Fiend showed me what puzzles people enjoyed and what solvers hated. I was lucky. I had stumbled into crosswords in the middle of a new golden era of indie puzzling.

*

In 2019, as I was still just learning how to solve, I started making miniature five-by-five crosswords before working up to the standard fifteen-by-fifteen grid. The clues were extremely specific to Minneapolis, where I was living at the time. HAI HAI, a popular Vietnamese restaurant that had opened recently, was vowel-heavy enough to be versatile in the grid. DANEZ Smith and HIEU Nguyen, two young poets who had just published collections with local presses, made appearances. A lot of the puzzles I made I didn’t finish. I just needed exercises to practice filling out the space.

One of the first puzzles I completed was Prince themed—RASPBERRY, “color for a beret,” COMPUTER, “blue item in Purple Rain?” The second one almost felt like one that could appear in a real puzzle, the color theme hopefully misdirecting the solver from immediately recognizing Purple Rain as a film title and “Computer Blue” as one of the songs that appears in it. Getting these two answers to sit across from each other, even in a lumpy, asymmetric grid I’d slapped together in Excel, was immensely satisfying. I wasn’t quite there yet, but I was starting to find that linguistic joyfulness that had first appealed to me. I knew these clues were well outside of general knowledge—that was the point. I wanted the specific and the niche. I knew who my audience was.

This was the final step because crosswords are meant to be solved by other people. I did something I had struggled to do with my own writing and shared what I made. And when I started asking other people to solve them, I realized that my interests that might have been dismissed as niche or frivolous were actually helpful. I couldn’t write the clues that The New York Times was full of—I’d never seen Colombo and had no interest in the great golfers of today, much less the 1960s. So as I moved from five-by-five to ten-by-ten puzzles, I wrote clues for Megan Thee Stallion (HOTTIES, “stans of savage singer”) or ’90s Black sitcoms (LATIFAH, “queen of living single”).

What makes a crossword go from good to great is the creator’s originality—their willingness to try a strange word, to develop a different theme at the risk of alienating part of the audience. As I said previously, clues and answers are reused frequently; it’s just the nature of English and our pesky attachment to vowels. Filling an animal-themed grid with OKAPIs or GECKOs seems like fun until you have to deal with those Ks and their refusal to precede most consonants. You’re better off with TAPIRs and GNUs and the rest of the tried-and-true menagerie of flexible and unfussy vocabulary. There are plenty of helpful crossword puzzle apps and dictionaries that will guide you into creating a puzzle; some even have an autofill to help you navigate tricky corners and write the clues for you. At a certain point, construction can become less an art than an act of dry mimicry.

One of the most frustrating things about making a puzzle is realizing that an answer you desperately want to use simply won’t work and you have to find a way around it. I have fallen into the trap many times of trying to force an answer, cramming it among other bad fill and explaining it away with convoluted clues—the squarest peg in the roundest hole. But what has always made the best puzzle is embracing the white boxes. You have to become unafraid of erasing all that hard work and continue to try something new, until you’ve made something better.

Once I started making crossword puzzles, language stopped being an unfriendly and amorphous beast. It was again a pleasure, a joy, something that was meant to be played with and shared. My interest in the subjects I included in my crosswords only deepened. Now I wanted to write more than three-word clues about them, and I wasn’t afraid to share what I had to say. And all the things I had learned from crosswords—to be unafraid of prickliness, to take indirect routes, to write and prioritize what I cared about, to be okay with a bunch of blank space—were now guiding my own narrative writing. I’m not good enough at making or solving puzzles to be precious about it. I just had to try—and it was the same way with writing.

There is more to learn from the crossword than trivia. I don’t do the crossword as frequently anymore, but every time I work on one I turn on that constructor part of my brain. I still don’t just want to solve it; I still want to understand it. Sometimes I’ll roll my eyes at an answer and figure out what I would change to make it work better. Other times I’ll admire a particularly ambitious gimmick and study its execution. The crossword sharpened my desire to construct better, to solve quicker, to understand not just if something works but why. I think most writers are motivated by that same desire. It’s why I keep trying to write more and write better, even if I never learn to solve in pen.

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