THE RIDDLES OF THE SPHINX: Inheriting the Feminist History of the Crossword Puzzle (2024), by media scholar Anna Shechtman (a former editor at Los Angeles Review of Books and currently an editor at large), is both a memoir and a cultural analysis of American crosswords from the 1910s through the 2010s. The book is also itself a kind of crossword, bringing together worlds that might not otherwise exist in the same place at the same time. Shechtman is a longtime crossword constructor, and constructors love answers that are 15 letters long because they traverse a standard American-sized puzzle grid. These answers, called grid-spanners, also often illuminate a larger theme or serve as seed entries from which the puzzle grows. Shechtman’s book has its own reveals and surprises too: one is CROSSWORD PUZZLE (15); another is ANOREXIA NERVOSA (15). Shechtman’s exploration of puzzle logic and anorexic thinking—and how she learned, physically and psychologically, to tease them apart—is the real enigma of her book-as-crossword.

Shechtman’s history is actually a “group portrait,” focusing on “women, [herself] included, who have attached themselves to language rules.” She begins by spotlighting Ruth Hale, a feminist activist who founded the Cross Word Puzzle League of America in 1924 and established bylaws that still characterize the game: interlocking, symmetry, and accessible words. On the surface, Hale—also the president of the Lucy Stone League, which advocated for married women to keep their last names—seems like a paragon of women’s liberation. Yet Shechtman astutely observes that Hale was also strictly rule-abiding: she eventually leaned so far into progressivism that, for her, even freedom became regulated. Hale’s diagramless puzzles, Shechtman points out, thus embody the paradox of her strict progressivism: “What looks like a wide-open grid, an expanse of freedom, is rigidly, but subliminally, rule-bound.”

Margaret Farrar, editor of Simon & Schuster’s crossword book series and the first puzzle editor at The New York Times, then takes center stage in Shechtman’s exploration of crosswords and domestication. Farrar shepherded the game from 1920s craze to household staple. Expanding on Hale’s rules, Farrar set a gold standard for grids and championed creativity, encouraging constructors to find new clueing angles, steering away from recycling (say, “World War II Battle” for BULGE) and toward fresher word choices, even if PROTUBERANCE or the spicier CONVEXITY seemed strange at first. As Shechtman writes, during the 1950s, Farrar began encouraging constructors to include themes, like Harold T. Bers’s feline-focused “Catalogue,” featuring KITTY ALLEN, KRAZY KAT, PUSSY WILLOW, and THE CATS MEOW. Yet Farrar chronically undersold herself, even crossing picket lines because she didn’t identify crossword-making as “labor.” At this point, for Farrar and the culture at large, puzzle construction was considered a leisure activity, so even when women were paid for the task, they were still not considered a part of the workforce. Not long after, when crosswords and puzzles became viable business ventures, and puzzle-making became a real job, women would find themselves on the other side, systemically barred from leading the crossword world that Farrar had helmed.

Shechtman’s most ambitious section is her discussion of sexual politics and semiotics. As she pointed out in an earlier essay on the subject published by The New Yorker, Jacques Lacan’s advice to budding psychoanalysts was “Do crossword puzzles.” Shechtman speculates about the connection between puzzles and analysis, writing in the essay that, “[l]ike Freudian analysis, or a linguistic Rorschach test, the puzzle creates meaning out of the chance encounters between words and images, proper and sometimes improper nouns, and acts as a window into our fantasies, tastes, and unyielding fixations.” In the book, she also elucidates the role of serious wordplay in the critical practice of écriture feminine, and explores how wordplay that might seem trivial in a crossword grid actually worked to undergird New Wave feminist theory. Shechtman focuses on the work of Julia Penelope, an activist and a “cunning linguist” who seemed to consolidate all of these ideas in her puzzles, creating crosswords with spellings like “wimmin” and deliberately arcane clues such as “___ and Melita (companion lovers who lived in Pelasgia) Answer: THALIE.” And yet, Penelope’s inflexible commitment to a lesbian lexicon and her politics as a lesbian separatist (as well as racist and transphobic statements), ended up alienating her from her peers. Words build worlds, but taking letters too literally promotes isolation.

Shechtman brings readers into the 21st century through her own story and her internship with legendary New York Times crossword editor Will Shortz. She held this position in 2013 and 2014, when the crossword world was undergoing many seismic shifts. Construction software was becoming ubiquitous, paralleling a rise in major outlets publishing the work of mostly male constructors. Though independent crossword puzzles were being published online at an increasing rate, offering new platforms for more diverse voices in puzzling, this very discrepancy between the major outlets and the indies exposed the implicit male domination that had taken over the landscape. Gone were the days of Ruth Hale and Margaret Farrar.

The personal side of the book is also the A plot of Riddles—a story of language rules, gender norms, and anorexia. (Shechtman wryly dubs herself “Anna Rexia,” riffing on rex, a male king: “I wanted to be both the hottest girl in school and a boy.”) Shechtman discusses the ways she herself has been written about (full disclosure: my own book on crosswords, which opened with an analysis of Shechtman’s influence, is discussed in one of the later chapters here). Shechtman is very much aware of how her own work and persona have situated her in the history of puzzling. Shechtman also ruthlessly depicts the connection between crosswords and the strictures of her eating disorder. As she recovered, she learned how to untether herself from the dangers of literalism. “Intellectualization” isn’t being an intellectual; “perfectionism” doesn’t mean perfect.

Shechtman’s depiction of her current relationship to crosswords has the elegiac tone of 1 Corinthians 13: “When I became a man, I put away childish things.” She mourns the primacy that software places on cultivating word lists—that is, continuously adding to and tweaking a weighted bank of words and phrases that the software uses to suggest fillers for the grid. Constructors use these lists to make certain that exciting phrases float to the top by virtue of their scores, but, perhaps more crucially, they use the scored-list system to suppress certain words, such as awkward abbreviations or very obscure terms that might be vowel-rich but that very few people will know. Shechtman calls construction “no longer a ‘space’ but an ongoing activity.” Yet crosswording has always been a state of mind. Farrar herself used an address book for her own proto–word list. And there’s this: today, more women than ever lead the puzzle vanguard, including Shechtman herself and Liz Maynes-Aminzade at The New Yorker, Patti Varol at the Los Angeles Times, Juliana Pache with her Black crosswords, and so many others.

Shechtman is delightful when sly—the “dic(k)tionary”!—and she sees the implications in every bit of linguistic play. From “Paradise” (rehab) to “Pleasantville” (her internship with Shortz), she has a preternatural gift for perceiving perfectly placed pieces of language. At the same time, linguistic games that seem to be the most fun also contain dangerous undersides—hence the CROSSWORDPUZZLE/ANOREXIANERVOSA double bind. Yet I found myself wishing that the book could crack into spontaneous joy. Paradoxically, where I do find some of that spontaneity is in arguably the most formally wound part: a crossword itself. Shechtman opens Riddles with an excellent original puzzle titled “I Pronouns Thee” that (spoiler warning!) features double-faced rebus squares that read one way going down and another across. This puzzle is complex but not convoluted, providing just the right kind of aha! moment. When you see through a grid, darkly, you can still have fun.