The Riddles of the Sphinx: Inheriting the Feminist History of the Crossword Puzzle

by Anna Shechtman

Combining the soul-baring confessional of Brain on Fire and the addictive storytelling of The Queen’s Gambit , a renowned puzzle creator’s compulsively readable memoir and history of the crossword puzzle as an unexpected site of women’s work and feminist protest. The indisputable “queen of crosswords,” Anna Shechtman published her first New York Times puzzle at age nineteen, and later, spearheaded the The New Yorker ’s popular crossword section. Working with a medium often criticized as exclusionary, elitist, and out-of-touch, Anna is one of very few women in the field of puzzle making, where she strives to make the everyday diversion more diverse. In this fascinating work—part memoir, part cultural analysis—she excavates the hidden history of the crossword and the overlooked women who have been central to its creation and evolution, from the “Crossword Craze” of the 1920s to the role of digital technology today. As she tells the story of her own experience in the CrossWorld, she analyzes the roles assigned to women in American culture, the boxes they’ve been allowed to fill, and the ways that they’ve used puzzles to negotiate the constraints and play of desire under patriarchy. The result is an unforgettable and engrossing work of art, a loving and revealing homage to one of our most treasured, entertaining, and ultimately political pastimes.

Genres: Nonfiction, History, Memoir, Feminism, Audiobook, Biography, Biography Memoir

288 pages, Paperback

First published March 5, 2024

Reviews

[Stephanie · Rating 1 out of 5]

I really wanted to like this one, but it’s officially joining the DNF pile today.

A book about the largely-unknown feminist history of the ubiquitous crossword puzzle, written by one of the few women to have made it in the very male and very white field of crossword publishing? That totally sounds like something I’d find interesting!

And to be fair, the parts where Shechtman talks about the history of and the social conditions in which crosswords really took off early in the 20th century are truly interesting.

Where she lost me was the frequent discussions of her experience with anorexia. Although she ties that in with how and why crosswords became a natural fixation and gift for her, I just honestly found there to be too much discussion of that and found it tedious. While I absolutely believe it is important to talk about and share our experiences with the difficulties we face, especially ones that are still a bit taboo, and wholeheartedly support people that do, this just didn’t feel like the right avenue for it.

I have no doubt that there are plenty of people who will love this book - I’m just not one of them.

My life is too short and my TBR pile is too tall to force my way through books that don’t resonate with me.

[Olivia Solbrig · Rating 4 out of 5]

When Abby brought this book home for me from the library, she said she thought this book was “made for me.” Which, TRUE!

I thought this was such an interesting and emotional combination of the history of crossword puzzles, the experience of anorexia, and growing into womanhood. I really enjoyed learning about the intricacies of constructing crosswords, and the intersections where that constructing meets culture, gender, privilege, and politics.

Minus one star only because I didn’t enjoy the third portion of the book. It felt far too long. This section focused on the French feminists and their ideas about language. Not only did I think it veered too far from the original topic, but it also felt like reading a textbook. The other sections of the text didn’t feel this way.

Overall I recommend this to a very specific audience.
1) If you are interested in the intersection between gender and language as it pertains to a “frivolous” pastime .
2) If you based your teen personality on being smarter than other people (me).
3) If you want an in-depth history on some of the major names in crossword history.
4) If you like in credibly niche non-fiction.

[Sarah-Hope · Rating 3 out of 5]

The Riddles of the Sphinx offers an interesting exploration of the role women have played in the invention, development, and popularity of the crossword puzzle. This is a hybrid sort of read: part history, part memoir, as the author, Anna Shechtman, is herself a creator of crosswords. The historic portions surprise and are contextualized in ways that connect the world of puzzling with key moments of 20th Century history. The memoir sections varied in their effectiveness. At times Shechtman's reflections illuminated her topic—at others, they illuminated her personal story more than the history of crosswords and felt extraneous.

I received a free electronic review copy of this title from the publisher via NetGalley; the opinions are my own.

[Mare · Rating 5 out of 5]

My friends, this book will not be for everyone.

In fact, this book is probably not for you.

But it found its way to me, and I found it extraordinary and difficult and beautiful.

Do you, like me, like books about complex, difficult women?

Are you, like me, still grappling with your internationalized misogyny after years of trying to adhere to feminist principles?

Did you, like me, avoid your feelings in your teen years by becoming the Smart One who does nothing wrong and only wants to achieve? To then discover somewhere along the way, you developed a completely unhealthy relationship with food?

Do you enjoy puzzles?

Well then, if you made it this far, hello! I hope you’re doing well. I’m also sorry. We deserved better, and we deserve to be better. (Also thinking about your feelings is not feeling your feelings - you feel them in your whole body. I know, I know, it’s weird at first but you’ll be fine.)

Reading this book was exhilarating. I inhaled it in two sittings - it’s a memoir about the devastation of eating disorders, loneliness, and obsession but also a thoughtful cultural history of the crossword puzzle. I love a book where an intelligent woman tells you a true story and tells you about all the parts of herself.

Anna is sometimes sarcastic and acidic, but able to make you feel for her and these complex women. Some paragraphs made me cry, and some made me laugh. But I was just utterly transfixed.

I’ve just finished the book, so maybe I’ll return to this review to flesh out my thoughts. But I really want this book to end up into the right hands - us smart, obsessive ladies in our twenties or thirties who’ve been told that we have to be smart to be valued, using our intellect to push people away when we’re really just really fucking lonely. I felt seen, and I hope you feel seen, too.

[Kendra · Rating 2 out of 5]

This is an ARC and will likely get copyedited, but: the clue for 1 Across in the frontispiece puzzle is incorrect. The place in question is where another diner orders "what she's having"; not Sally herself. The tone is prickly and snooty throughout, which made a lot of it off-putting. I don't need an author to constantly be showing the reader how smart they are compared with everyone the discuss in the book. Schechtman opens by connecting her nascent puzzle-making with her anorexia, and draws a lot of striking parallels, but the writing here feels disjointed and loose; again, I'm sure copyediting will help with that. I do think pitching this as a memoir that also documents the work of other women puzzle constructors would be better than marketing it as a book about the crossword and feminism.

[Elaine · Rating 3 out of 5]

I am sorry, but I don't even know what to say about this book. Is it meant to be an autobiography on the author's battle with anorexia? A discussion on feminism? On French feminists? A little of the history of crossword puzzles? I found this to be a difficult book to read as I had a difficult time following the thread of this story - or stories. While I appreciate that the author is a very educated woman who is intimately involved with the world of crossword constructors, I am not certain I agree that anorexia plays a role in this history. I found the individual sections describing some of the feminists' struggles to be quite interesting, and the discussion about the more recent feminists to be fascinating, but I found other, earlier sections to be a difficult, very 'high brow' read, as if the author was more interested in proving her 'smarts' as opposed to giving a more straightforward history and discussion. I did like the analogy of the female constructors fitting into the crossword squares, it's an interesting comparison. There are some bright spots in this volume but I can't wholeheartedly recommend it.

This ARC was provided by the publisher and by NetGalley, the opinions expressed herein are strictly my own.

[Sarah · Rating 3 out of 5]

I think this book is branded really surprisingly—rather than a text about the feminist history of crossword puzzles, this is primarily a memoir, largely centered on the author’s struggles with anorexia, her experience constructing puzzles, and her attempts to make sense of the world by reading different feminist philosophers. A lot of the crossword content is quite oblique/indirect, which I was disappointed by. Shechtman does acknowledge that her tendency to intellectualize led her “to believe I could describe my past (my eating disorder, my crossword puzzles) as a memoir deflected away from feeling, a memoir wrapped in a cultural history” which I think sums it up pretty well. I wish she had had a little less muddled idea of what this book was supposed to accomplish!

[Jessica J. · Rating 3 out of 5]

This is a mixture of memoir and the history of women in crossword puzzle construction. The history part is fascinating; the memor often feels shoved in awkwardly. Schechtman leans really hard into literary theory and psychoanalysis in a way that felt rather...detached? I think she wanted this to help tie the two parts of the book together, but I don't think it does so successfully. I'd read the history and skim over the memoir and theory.

Note that the description of this book fails to mention that the memoir portion focuses very heavily on disordered eating (the author's struggle with anorexia) so insert content warning here.

[nomi]

feminism, psychoanalysis, and puzzles… so me fr

[Ben · Rating 3 out of 5]

Thanks to NetGalley and HarperOne for the ARC of this title.

I think the subtitle and blurb-y/PR info on this title are going to do it a disservice to potential readers. Everything is focusing on the _crossword_ bit, when that feels ultimately secondary to the memoir parts of the book. I feel like the readers who come to this for the crossword side are going to be unfulfilled, and not enough is playing up the memoir side to bring in the potential audience there.

There's two strands of narrative going on throughout the book - the author's process of dealing with anorexia and how crossword construction played into that on both sides of that journey, and the stories unsung women who either affected the development and popularization of the crossword, or used it as a tool for further exploration of feminism. There's attempts to braid these together in each chapter of the book, but I almost feel if the personal memoir bits and the historical research-y bits (which are really good, and show the author's skill for highlighting these women's contributions) should have been further separated into their own chapters - there's not quite enough braiding these together, and alternating these in the book could have helped strengthen both sides for me.

[Ashley D · Rating 3 out of 5]

i wanted to LOVE this book but i simply did not. i was unaware when i started it (stuck in the airport…bad omen) that it would be part memoir. that was the absolute worst part for me. she discussed her eating disorder for easily half of this book and i get that for her it is intertwined with her puzzling background but i just hated it. found it deeply upsetting and i didn’t love reading about it. the actually history and feminism i enjoyed and the actual puzzling i enjoyed which is what saved this from a 1 or 2 star review. but i just didn’t love this the way i wanted. i also read over half of it the first day i read it and then didn’t touch it for like two weeks which also …not a good omen. idk overall i found this disappointing but a saving grace is that at least it wasn’t freakishly long so i didn’t have to suffer through like 500 pages of it. also last thought is i distinctly remember some freud psychology in there like psychoanalysis and i just can’t take that seriously either bc the man was a freak

[Drew Praskovich · Rating 4 out of 5]

From the moral panic at the origin of crosswords and Freudian analysis for eating disorders and French feminism.

Shechtman’s has forever changed how I will look at these puzzles. Far much more nuances than a simple black and white grid.

[Jennifer · Rating 5 out of 5]

This book felt very purpose-written for me. It was like a quick review of the waves of feminism, of feminist and literary theory, plus of course crosswords (one of my favorite things). Big big trigger warnings for her personal account of anorexia, but I found this absolutely delightful. Like going back to grad school (the English program) for a few days, with all the good parts and little of the bad.

[Beau Pennington · Rating 2 out of 5]

I’m convinced non fiction is not for me. This book is about the history of crossword puzzles and the women who influenced it. It’s a very niche book with a variety of themes discussed including feminism, sexuality, psychoanalysis, anorexia and the influence of language. There were a few parts that were interesting to me. Mostly got this book to listen on my walks and it would have been hard for me to finish it if I was reading it.

[Liz Mc2 · Rating 4 out of 5]

I didn’t read the description carefully and wasn’t expecting the parts about the author’s struggle with anorexia—so a warning if that’s a topic you’d prefer to avoid. This was a fascinating and wide-ranging book, including biographies of women who were foundational to the establishment of crossword puzzles (now seen as very much a male preserve), feminist crosswords, meditations on the wordplay of French feminist theory and James Joyce, and the author’s own experience of making crosswords and working for Will Shortz. Shechtman draws so many interesting connections, including how both her anorexia and her crossword constructing were about her desire to prove herself as a good, smart girl, and to exert control. I really enjoyed it. (Because I listened to a library audiobook I missed out on the crossword she included).

[Carolyn · Rating 3 out of 5]

I listened to this on audio which reaffirmed my inability to comprehend anything I hear. One moment she’s talking about feminism or a constructor of crossword puzzles and the next it was about her time at an anorexia treatment center. Maybe I would have liked it more if I read it, but it might have been too dull for me.

The best part about this was her saying it is okay to look up crossword clues to learn something, as I usually leave the ones I don’t know blank since it feels like “cheating” to look things up.

[Emma Lester · Rating 1 out of 5]

Couldn’t finish this book. Disappointing bc it came recommended but was (weirdly?) mostly about her eating disorder and not about writing crosswords which is what I was interested in.

[Amanda · Rating 3 out of 5]

2.5, rounding up. I put this on hold because I thought it was more about the history of the crossword, and there is some of that, with profiles of important women who played roles in shaping the crossword as we know it today. However, there's also a lot of French feminist literary theory (and theory in general), and a pretty intense memoir of the author's experience with (and recovery from) anorexia. The description doesn't mention any of that, which isn't the author's fault, necessarily, but I felt misled and considered not finishing this. I kind of feel like this needs more clarity in the description, or at least some sort of content warning. I did like the crossword-related parts, though.

[Selina · Rating 5 out of 5]

a bit of a dense read and only worth it if you're either into crosswords or have some deep perfectionist tendencies. i've never seen myself so clearly reflected in a book and schectman does a great job connecting disparate themes into one cohesive narrative

[Madi Macera]

I stumbled upon Anna Shechtman several years ago when I revived my love of crosswords. I have completed several puzzles by her and enjoy her constructions and wordplay. I think this book is masterful for a few reasons. Shechtman’s story being so inherently tied to crosswords and her ability to express herself while deep-diving into the fascinating intersection of the female impact (and really inception) of what we know as the crossword is lovely.

She hails many women constructors while recognizing equally the limited view of this being largely cis white women (and transitioning massively into dominated by cis white men). It is a strong narrative and commentary of mental illness, history, sociology, and linguistics. It would be a disservice for me to not let a few quotes speak for themselves.

“Passion projects are a social privilege, and as most women are still expected to do the majority of childcare and housekeeping as well as work full-time, few find time for this rarified, underpaid work… But like botany, film editing, library science, and computing before it, it was once a form of feminized labor.”

“The crossword puzzle, under Margaret's stewardship-and today, according to her legacy—is a conservative cultural product. Conservative in both senses of the word: traditionalist (few create or solve crosswords to change the culture but to assert their fluency in it) and self-preserving a crossword is a coping mechanism, a way of feeling in control of the culture, even when you've lost it or could never lay claim to it to begin with).”

“…[She’d] like to think that language's potency is its most brilliant resource. We can use its constraints to harden our self-conceptions, to resist the painful ineffability of embodied experience, and to crystallize our difference from others. We can wound, and we probably always will, but we can try not to.”

"’So much of crossword-making is gatekept. Something you notice about people who value intellect is that there is this pride in being the 'only person' who can do something. [It cultivates] the idea of genius, which I understand to be related to access and privilege.’"

"’[She] was robbed of a chance to learn about crosswords at a young age in part because crossword culture does not encourage learning —rather, it rewards already knowing.’”

“To ask these questions is to concede to such a thing as women's language, a separatist lexicon that maybe shouldn't be used by or for men. It is to sit between unsavory cultural stereotypes, on the one hand, and gender essentialism, on the other…How can women fight for cultural equity without conceding their difference in the very terms that would objectify them? Can women ever create in a culture that is not properly their own? These were the very questions that plagued the French Feminists, the American sociolinguists, and their critics fifty years ago. They puzzle me now.”

Lastly, the detail of included a crossword in the front is incredible. I ended eyes-open; I felt emboldened, enlightened, attuned, seen, and ready to solve some puzzles.

[Lucy Johnston · Rating 4 out of 5]

My mom got this for me and it was a 🎯!

A couple times, I questioned the conclusions the author was drawing. I'd be with her point by point, but then we'd arrive at a perfect feminist-crossword intersection and I'd get skeptical. "Oh really, crossword solvers in the 20s were viewed as wildly oversexed? 🙄 Awfully convenient for the point you're trying to make in this chapter."

And THEN, I'd turn the page and she's inserted a political cartoon from the time that completely proves her point. Something like a flapper saying "I think the answer to 4-across is 'naughty' 😉😘🫦" Like okay, how about I sit down and shut up, because she clearly knows what she's talking about.

Other ones that got me:
- "She's for sure overstating how much people associated crosswords with hysteria." Crossword Sanitorium. "Ok never mind."
- "The black/white of the crossword reflected the racism of the time? That's a stretch." Super racist cartoon about the difference between black and white squares. "Never mind."
-"She's making too much of the connection between early programming and crosswords." Programming recruitment questions. "Yeah how about I just listen from here on out."

A lot of the Freud/French feminism stuff went over my head, but you know what, I'm not about to doubt its relevance! Great read

[Emma · Rating 3 out of 5]

I did not know exactly what this was when I picked it up. But it turns out the book didn't, either. The subtitle does describe some of the book: it's partly about the women who helped shape crossword puzzle culture in the U.S. Many of these women have interesting stories, and I enjoyed learning about them.

What I wasn't prepared for was for this to be an anorexia memoir. The author spends almost as much time musing over how and why she became anorexic, and how she evaded and finally sought treatment, as she does writing about crosswords. Which, after all, are the thing in the title! She goes into so much detail on anorexia that I really think it should have been a bigger part of the marketing for the book. I can easily see how someone in recovery could pick this up thinking it would be about crosswords and get triggered.

Even if the book had been marketed better, I would still think it was too meandering. The connections to anorexia are often tenuous at best, but I have a feeling this wouldn't have been long enough for a book if they were removed. One of the later chapters about women working as "human computers" was great, and I wish the whole book had been like that. Still an enjoyable read, especially if you're constantly getting asked for help with crossword puzzle clues by your father.

[jasper · Rating 4 out of 5]

3.5. this book was a much deeper meditation on gender and/in media than I expected to get. I found myself realizing in the early chapters that no one has ever given me a particularly serious explanation for having decided to pursue crossword construction. shechtman's is striking and somewhat startlingly familiar — she sees some things about self-expression and purpose in the grid that I recognize but hadn't been able to articulate. combined with the historical analysis of what crosswords meant for the early women who pioneered and edited them, and what that reveals about the wider genre, this is quite an original contribution to the ecosystem. I'm not as sure what someone with no interest in the context around puzzles, or particularly a sense of the inside baseball around editing tugs-of-war that shechtman touches on from time to time, would get out of this, but a provocative read in any case.

[Neil Fitzgerald · Rating 2 out of 5]

Declaring bankruptcy on this one, DNF after 100 pages.

The premise sounds amazing: a semiautobiographical feminist psychoanalytic history of crosswords by a pro constructor? Hell yeah. Unfortunately, while the raw material is frequently interesting, the disparate threads don't add up to more than the sum of their parts. This book feels like a really cool pitch in search of a thesis. Toting this book around New York did net me some juicy gossip about indie crossword constructors, but that was probably the best part about it.

If you're in the market for a playful and political reflection on wordplay, though, may I recommend Counterfeit Monkey ?

[elizabeth · Rating 5 out of 5]

→ 4.5 stars (★★★★.5)

my dad recommended this book to me, and i loved it! it was very informative and interesting, and i enjoyed the synthesis between the history of crosswords and the author's eating disorder. i also appreciated how Shechtman discussed both the contributions and the shortcomings of the feminist figures she highlighted; i think it's important to celebrate feminist progress without overlooking the racism, transphobia, and other bigotry that many of these women perpetuated. overall, a great read!

[Jo · Rating 3 out of 5]

Less than half of this book was about crosswords, which was disappointing.  As many other reviewers have noted, the marketing should have been more clear about this being primarily a memoir about anorexia. The non-crossword stuff was interesting at times, but the weird French feminists piece in the middle felt out of place and snobbish, and it was unclear how the entire second section was linked to puzzling.

[Kaitlyn Andrey · Rating 4 out of 5]

The Riddles of the Sphinx was about as tailored to my interests as a memoir adjacent book could possible get. I did struggle to get through some parts but overall this book neatly explored many of the concepts I like to consider as an avid puzzler/newbie constructor/feminist. The author has earned all of her accolades and undertook an important project in describing a piece of our lost history.

[Diael Thomas · Rating 4 out of 5]

Loved it for the deep dive into the history of crosswords and intersection with second wave feminism. The book did an amazing job explaining how language can be transformed to subvert the patriarchal origins and recognize marginalized identities. Buuuuut I would have liked a trigger warning for the discussion of the authors eating disorder which was central to and woven through the whole book.

[Megan · Rating 5 out of 5]

Audio. I simultaneously loved and hated this book. I enjoyed learning about the seamy underbelly of the crossword world, but hated the endless chapters on French Feminist theory, despite the two being linked carefully by the author. I did appreciate her discussion of how word lists are created and how they can further marginalize already marginalized communities. An excellent read, despite my conflicting feelings.

[Isabel · Rating 4 out of 5]

Like some other reviewers said, this book is definitely not for everyone. It's extremely niche, partially a feminist history of crosswords, and part memoir. At times, it was tough to read because of the academic language. Lots of theory (Freudian and French feminist). Despite this, it was a fascinating read.
I hadn't expected the memoir aspect of it to be so personal, but I still found it interesting.