Between the Black Squares and the Blank Ones

Somewhere between the black squares and the empty ones, Anna Shechtman found a structure she needed long before she understood why. The Riddles of the Sphinx begins with that recognition, tentative at first, then sharp, as she looks back at the grids she built as a teenager and sees not a hobby, but a blueprint for how she learned to manage a self she feared might collapse. The book presents itself as a history of crosswords, a memoir, a feminist inquiry. What it actually becomes is a story about control, language, and the fragile balance between the order we seek and the order that begins to seek us.

Shechtman started constructing puzzles at fifteen. Most people chalk that up to precocity, but she treats it as something more pointed: an early instinct to retreat into systems where rules never shifted, and logic could be trusted. She was nineteen when The New York Times accepted her first puzzle, a milestone that should have felt like an arrival but instead deepened the split she was already feeling. Her world narrowed into the grid on one side and anorexia on the other, both offering precision, discipline, the illusion of mastery. She writes about this not as a metaphor but as lived architecture. The symmetry calmed her. The rules sustained her. The consequences were something she only understood years later, when she had to separate the language she loved from the system that was consuming her.

Before she lets you into that private reckoning, she maps the lineage of women who shaped the crossword long before men formalized it as a cultural trophy. Ruth Hale stands first: a feminist activist with a near-religious devotion to language rules. Hale founded the Cross Word Puzzle League of America in 1924 and established the bylaws that still define the American puzzle’s grammar. Her politics leaned radical; her structure leaned rigid. It’s a tension Shechtman grasps immediately: Hale promised freedom while enforcing constraint, creating diagramless puzzles that looked open but were quietly governed by invisible strictures. For Shechtman, Hale’s paradox lands close to home, the way a pursuit of clarity can become a cage when you cling to its rules too closely.

Margaret Farrar follows, the steady hand who shaped the puzzle’s midcentury identity. As the first crossword editor of The New York Times, she championed themes, freshness, and originality. She pushed constructors toward riskier vocabulary rather than stale clues. Yet while she elevated the puzzle into an intellectual ritual, she didn’t claim the authority she held. She saw her labor as leisure; she dismissed her influence even as she set the standard that others followed. When crosswords became a business, men assumed the professional mantle, pushing women to the margins of the very world they had built. Shechtman doesn’t sermonize about this. She simply shows the pattern: women stabilizing a form, then quietly stepping aside when that form acquires prestige.

Julia Penelope enters next, a voice both brilliant and uncompromising. A linguist, theorist, and lesbian separatist, Penelope built puzzles as political statements, spellings like “wimmin,” mythic lovers from arcane genealogies, lesbian-coded clues designed to disrupt mainstream expectations. Her puzzles were worlds, but hermetic ones. The same devotion to linguistic purity that made them radical also made them isolating. Shechtman handles this with honesty, acknowledging the power of Penelope’s project while tracing the cost of reducing language to ideology. Words can liberate; they can also narrow until they shut out the very community they’re meant to serve.

Only after she builds this portrait of her predecessors does Shechtman shift the lens toward her internship with Will Shortz, where the 21st-century crossword world reveals itself as something far more fractured. Construction software was on the rise, word lists were becoming standardized, and editorial culture at major outlets was heavily male. Independent puzzles thrived online with a more diverse range of voices, but the mainstream remained stubbornly narrow. Shechtman understood early that she was both heir and outsider, inheriting a lineage that the contemporary puzzle world rarely acknowledged. The dissonance left its mark.

This is where the book turns inward, where her own story becomes the quiet force guiding everything else. She writes with startling clarity about how anorexia wound itself around her identity, how its ritualistic logic mirrored the mental grid she inhabited as a constructor. There is nothing melodramatic in how she tells it. If anything, the restraint is its own form of truth-telling. She describes how perfectionism masqueraded as strength, how she mistook control for competence, and how literalism turned into punishment. Shechtman’s recovery becomes less about abandoning rules and more about learning which ones were never meant to govern her life in the first place.

The intellectual spine of the book, its semiotics, psychoanalysis, and feminist theory, supports, rather than overshadows, the personal narrative. She resurrects Lacan’s advice to analysts, “Do crossword puzzles,” and follows it into an exploration of how puzzles mimic the associative play of the unconscious. She connects crossword wordplay to écriture féminine, showing how seemingly trivial manipulations of language can disrupt patriarchal meaning structures. Nothing in her analysis feels ornamental. She isn’t padding the text with theoretical citations; she’s illuminating the political and psychological stakes of a form most people treat as background noise.

Her critique of the construction software era carries a different kind of sadness. She mourns the intimacy that was lost when puzzles became partially automated. The craft used to rely on the constructor’s ear, on human resonance, and risk. Now, scoring systems and word lists decide which entries rise to the top. Shechtman doesn’t treat this shift as a catastrophe, but as a loss of texture, a soft erosion of the personal voice that once defined the best puzzles. And yet she acknowledges the continuity. Farrar kept her own analog word list. Every era has its tools; every era tries to refine the balance between freedom and constraint.

The book’s emotional register is clearest when she writes about what crosswords offered during the pandemic: a quiet distraction, a momentary grid of order against a backdrop of chaos. Margaret Farrar once said, “You can’t think of your troubles while solving a crossword,” and Shechtman sees the truth in that. But she also understands the tension inherent in that relief. A crossword presents a world where every blank has an answer, where every letter belongs somewhere. Real life never cooperates like that. Maybe that’s why she kept returning to the grid. It wasn’t escape; it was rehearsal for the courage she would eventually need.

By the time the book reaches its final third, Shechtman has learned to tell the difference between the systems that protected her and the ones that harmed her. She doesn’t present recovery as triumph. She presents it as understanding, understanding that perfection isn’t strength, that language doesn’t exist to shrink our world, that order should help us breathe rather than deprive us of air. She writes with a voice sharpened by scholarship and softened by experience, and that combination gives the book its resonance.

For me, this was a four-star read: intelligent, complicated, sometimes wound tighter than it needs to be, but undeniably worthwhile. The book succeeds because it doesn’t pretend puzzles are trivial. It takes seriously the idea that the systems we cling to, grids, rules, rituals, tell us more about our fear than our intellect. Shechtman shows that crosswords can be escape hatches, intellectual playgrounds, political battlegrounds, or mirrors, depending on who’s holding the pencil. But above all, she shows that language, even in its most orderly form, is not what saves you. It’s what helps you find your way back to yourself once you decide to stop living inside the empty squares.

Image © Shutterstock, Asset ID 2691960557, uploaded October 18, 2025. Used under license.

Hameltion. Anna Shechtman at the 2024 American Crossword Puzzle Tournament. 6 April 2024. Own work. Licensed under Creative Commons Attribution–ShareAlike 4.0 International (CC BY-SA 4.0).