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.