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From Square One: A Meditation, with Digressions, on Crosswords

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From Square One is Dean Olsher's captivating and in-depth exploration of the cultural history, psychology, and even metaphysics of crosswords -- their promise of a world without chaos and uncertainty. It is often repeated that more than 50 million Americans do crossword puzzles on a regular basis. Skeptical of that claim, Dean Olsher does his own research and finds that the number is nearly dead-on. Filled with lively, original reporting, From Square One disputes the widely held belief that solving crosswords helps prevent Alzheimer's; in fact, the drive to fill in empty spaces is more likely a mental illness than a cure. While "puzzle addiction" is usually meant as a lighthearted metaphor, the term contains more than a nugget of truth. Olsher looks into the origins and traditions of this popular pastime, which made its debut in a New York newspaper in 1913. Or did it? Along the way, he takes readers inside the making of a crossword. He also revives the quest of m

192 pages, Hardcover

First published June 23, 2009

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Dean Olsher

4 books

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5 stars
4 (3%)
4 stars
29 (28%)
3 stars
34 (33%)
2 stars
31 (30%)
1 star
4 (3%)
Displaying 1 - 30 of 32 reviews
Profile Image for Ruel.
130 reviews18 followers
February 12, 2014
I love crosswords and "From Square One" seemed to be right up my alley, but it wasn't. Perhaps I should have paid more attention to the title of this book: it's a meditation first, with digressions second, and crosswords last.

The only reason why I gave this two stars is because the information on crosswords is quite good: some history, a few amusing anecdotes, and interactions with crossword royalty (Will Shortz and others). I thoroughly enjoyed these sections, but nearly skipped anything to do with his failed radio show, marriage, and struggles with his parents. I didn't listen to Olsher's now-cancelled NPR show, so maybe I would've appreciated his book more if I was a fan. It's a quick and light read for a night, even if scattered and unfocused.

My main problem with this book, however, is Olsher's early claim that he is not an Anglophile, which then leads to him spending most of this book trying to convince us that the English version of crossword puzzles (cryptic crosswords) is far superior and must replace the inferior American crosswords. It's during these passages that he comes off as smug and unlikable.

My suggestion for fellow crossword fans: flip through this at your local library for the crossword history and anecdotes and skip everything else. Definitely worth the 20-30 minutes of your time.
Profile Image for Steve.
91 reviews15 followers
June 30, 2009
How to Write a Book About Nothing by Dean Olsher.
Profile Image for Dee.
367 reviews
January 27, 2010
Wonderfully nerdy.

p. 45: "The pleasure principle [is:] overrated. Instead, we are primarily motivated to create challenges for ourselves that we can overcome. This drive for satisfaction, which manifests itself whether we're solving puzzles, running marathons, or engaging in S&M (for some people, anyway), is hardwired into our brains."

1,598 reviews40 followers
November 6, 2019
some interesting crossword history tidbits [British intelligence in WW II used a crossword puzzle competition to select some recruits for a major code-breaking task; Merl Reagle, who went on to be Sunday Wx Post puzzle person, was recipient of a "letter to a young constructor" at age 16 [p. 88], featuring advice from some crossword vet].....

and some enjoyment of recognition (oh no, not Mel Ott or Bobby Orr again, wielding an "epee" or any of the other grossly overused clues].....

but for the most part not that coherent or engaging a book. "meditation, with digressions" is about right as a way to characterize it -- doesn't stick with any thought or issue very long.

maybe also relevant to my tepid reaction is that i totally disagree with his strong preference for "cryptic" crosswords as appear in Harper's and what not, as opposed to the standard "definitional" ones. Much much prefer the standard ones, and it's a little boring to read at length someone's expression of taste on this. It's as though i like french vanilla and he likes chocolate fudge ice cream from Baskin-Robbins and just keeps on telling me how great it is.

Profile Image for Nip.
152 reviews2 followers
March 31, 2024
A mess of a book. Pointless, disorganized, meandering. Not incidentally, Olsher closes his "meditation" by deciding he's had it with crosswords and wants to become a musician... Which he did -- according to Google -- as well as becoming a psychotherapist specializing in trauma. Probably time for me to stop trying to find a good book about crossword puzzles!
6 reviews1 follower
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March 5, 2017
Electronic Book Cards


Author Background: Dean Olsher has been a radio broadcaster for more than thirty years. He was an arts and culture Correspondent for NPR News as well as host and creator of The Next Big Thing.


Literary Time Period: the book was written in the Early 2000’s, but the time period of the story was around the mid to late 1900’s in America.


Setting: thought this was a book of more philosophy and psychological studies pertaining to crosswords, but this story also does bring up parts of Other's past but nothing to descriptive at all.


Characters: Again Since this isn't an a story book, there weren't to many key characters at all. If I had to list some thought it would be the author himself and his wife, the only two people brought up in this book.

Nothing much was said about Dean's wife, describing her as an individual. Only that she wasn’t fond of him spending so much time with his studies in literary work. Dean was a very intellectually advanced man, especially in the field of entertainment, rhetoric, and psychology. He was a thirty year broadcaster and the creator and of host of The Next Big Thing.

Theme: There was no literary theme behind this book due to it not having a storyline, this book was about the logic and psychology behind crosswords.

Plot: this book (in deep detail) thoroughly describes the logistics behind crossword, how exactly the creators of them figure out ways and words used to trick or confuse the people receiving and trying to solve them. Also somewhat of the science behind how it exactly teases the human brain and the psychological overview of how the mind works during solving them.
180 reviews8 followers
August 1, 2009
This guy was pretty obnoxious. I probably wouldn't have read past the introduction if Lani hadn't recommended it. He kept making unnecessary snide remarks about politics (Bush administration and, even less topically, Linda Tripp ... really, Olsher, not even Clinton still cares about Linda Tripp), and he kept going off into his own psychological issues and only very tentatively, if at all, connecting them to crossword puzzles. Annoying.

Oh, and he quotes T.S. Eliot saying something pretentious. Namely: "Poetry is not a turning loose of emotion, but an escape from emotion; it is not the expression of personality, but an escape from personality. But, of course, only those who have personality and emotions know what it means to want to escape from these things." And as if it isn't catty enough when Eliot says it about poetry, Olsher wants to apply the same thought to crossword puzzles. T.S. Eliot fans are jerks.

However, he did grow on me a little when it became clear that his book is really a sneaky manifesto in favor of cryptic crossword puzzles. Also, he faithfully narrated when various people he interviewed thought he was being way too pretentious and over-reaching in his analysis of crossword puzzles, which was kind of awesomely self-aware and made me like him a little more. If you can admit when people think you're an asshole, you're probably not all bad.

Plus, he interviews Colin Dexter, who apparently named Inspector Morse for a fellow puzzler he'd never met in person. He also interviews Stephen Sondheim, a guy who constructs crossword puzzles for a living, and a guy who got into crossword puzzles while in jail serving time for flashing children. Each of these interviews is individually worth sitting through at least 10 pages of Olsher's less interesting prattle, so the book balances out well on the whole.

Plus, I still have 8 hours to kill in the hotel before I go to work today, and he includes a cryptic crossword for me to do.
Profile Image for Jillian.
177 reviews5 followers
May 21, 2012
I don't always read non-fiction.

But when I do, I read about a topic I love and it's written by a former correspondent for NPR.

"From Square One" is a lovely, quick read. It's more an interesting memoir about a personal relationship with crosswords than an historical account or a philosophical explication of crossword puzzles. Olsher writes like any good radio personality speaks: never overbearing and when humorous is wittily so--those kinds of punchlines that hit you two sentences later and make you chortle to yourself even when you're in public.

The conclusion I came to after finishing is that everyone goes to crossword puzzles for different reasons, the way everyone goes to alcohol for different reasons, but we all have overlapping habits to some extent (for example, Olsher and I both make a personal rule for easier Monday/Tuesday puzzles: we only allow ourselves to solve words attached to the Across-1), the way lots of alcoholics have overlapping extraneous habits (for example, always following one drink with a second drink, or whatever alcoholics do). In any case, Olsher's personal anecdotes and his interviews/encounters with other crossword enthusiasts comforted me with a feeling of solidarity. They also challenged me to exercise my mind more. They also depressed me with a reminder that there are people like 20-year-old Tyler Hinman who can finish a Saturday "Times" puzzle in just over four minutes. (I think my personal record is thirteen words on Saturday.)

Overall, "FSO" reads easily, and if it does anything for you, it will surely make you want to go out and buy a newspaper.
Profile Image for Evanston Public  Library.
665 reviews67 followers
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July 24, 2009
Is a crossword puzzle part of your daily routine? Do you use pencil or pen? Do you time yourself (i.e., are you in some way competitive)? Do you know anything about the history of crosswords? Dean Olsher, NPR commentator, offers his take on these and other word puzzle issues, some surprisingly thorny. He suggests that for some of us puzzlers, solving a word puzzle is more satisfying than solving a number puzzle like Sudoku. Why? Well, it has something to do with the denotation and connotation behind every word we fill in. Each one evokes a story, a history, a connection to our culture even if we are only marginally aware of this as we plug in those tidy white squares. In the course of Olsher’s meditation, we follow a master puzzle creator, or “constructor,” design a complex form of crossword popular in England that uses puns, double entendres, and couched directions that Olsher would love to see gain popularity here (note: I’m good at standard puzzles, but these are beyond me). This highly entertaining treatise is a good reading choice for puzzlers and non-puzzlers alike. As one reviewer commented, “If Dean Olsher wrote a book on the history of plumbing supplies, I’d snap it up.” Me, too! (Barbara L., Reader’s Services)
Profile Image for Linda.
24 reviews
September 25, 2009
I love a good crossword puzzle, so I thought this book would provide insight into the quirky personalities who write crosswords and those who plan their days around completing them. It started off great with lots of intelligent and witty insights, but then slowly deteriorated into a rambling travelogue/monologue of the author's take on a select group of players and competitions. The rest of the book was abruptly hijacked into a revery about a certain type of crossword - the "cryptic crossword"- its vast superiority to all others, and a final chapter attempting to force the reader into the same conclusion! If you are fascinated by crosswords, and the nerds who obsess over them, skip this book and rent the wonderful documentary "Wordplay". It's a great film and will give you all the satisfaction that should have come through here.
Profile Image for Cade.
651 reviews43 followers
July 17, 2011
I am a complete sucker nonfiction, especially about my own obsessions, hobbies, and loves. So when I stumbled on this one at the Dollar Tree, how could I not pick it up? Nonfic? Crosswords? A dollar? Yes, please. Unfortunately, the book was rather disappointing. Not that it wasn't well written. On the contrary, Olsher is quite a good writer. It isn't that I wasn't interested. I love crosswords. The problem lies more in the organization. At times, it felt as though I was reading something written by a person with relatively uncontrolled multiple personality disorder. He jumps from topic to topic and back again with far too much frequency for my taste, which is really unfortunate, because I think had it been better structured, it would be a 5 star book. I did enjoy it though, if for no other reason than I learned a few bits of odd trivia.
Profile Image for Patty.
2,688 reviews118 followers
November 7, 2009
I haven't done a crossword puzzle for some time. And cryptic crosswords - I never understood them. There was a point in my life that I did the NYT puzzles, but I hadn't really missed them. Until now.

Olsher has written a book that has rekindled my interest. I don't think that was his intention. I think Olsher is just fascinated with crosswords and had to share his obsession. He did a good job of telling his story, his involvement with crosswords.

And for me, besides learning all kinds of odd facts about crossword puzzles, I finally understand cryptic crosswords. Thank you Mr. Olsher.
Profile Image for Lani.
789 reviews43 followers
September 12, 2009
While the author is rather obnoxious, the book is still pretty interesting. I'm not quite the crossword nerd that many of these people are, but I enjoy learning the weird esoteric trivia as much as the other losers.

The interviews are fun, and the discussions with Will Shortz are pretty interesting. In general I guess I had never given all that much thought to the production or development of crossword puzzles. Neat stuff!

If you're willing to laugh at the pretentiousness of the author, it's a pretty enjoyable book. For crossword dorks anyway.
Profile Image for David.
401 reviews
June 22, 2016
A book written by a pretentious crosswords snob for pretentious crossword snobs. While there we're a few interesting tidbits of information in the book-such as famous people who like crosswords, and comparisons between doing crosswords and taking a cruise as real-world escapes-the book talks about people and words that I haven't heard of. I consider myself a fairly educated, intelligent person-I have a Masters Degree and listen to NPR every day-but for those who don't do the New York Times crossword (or any crosswords-in my case). I felt like I wasn't on the author's level.
Profile Image for Jeffrey.
73 reviews1 follower
August 28, 2009
This is a frustrating book, because he talks about achieving a flow state when doing puzzles or listening to music, but the prose jumps around from topic to topic such that achieving a flow state reading the book is impossible.

There is a cryptic crossword by Francis Heaney in the back, though, which is a plus.
238 reviews10 followers
February 27, 2010
This book is partly a history of crossword puzzles, partly a collection of quotes and stories from crossword puzzle enthusiasts, and partly an attempt to find deeper meaning in crossword puzzles and the enthusiasm that they command.

I wish there was more history; then again, how much history is there? The best part of the book was the cryptic crossword at the end.
Profile Image for Cyd.
568 reviews14 followers
September 22, 2012
I found much of this book--perhaps especially Olsher's thoughts on the mental illness aspects of crossword puzzles--quite familiar. I concluded that I don't care whether periodic crossword binges are proof that I am seriously mentally ill...since that is already an otherwise established fact. Anyone who has a similar obsession with crossword puzzles will likely find this book fascinating.
Profile Image for Gloria.
861 reviews33 followers
December 27, 2015
Oh my… I'm afraid I have many similar tendencies that Olsher has… and he has succeeded in resparking my interest (and hope that one day I might solve) acrostics.... Having instructions from Ximenes regarding the types of clueing is a helpful—maybe. I still am baffled by the one included at the end of the book....
Profile Image for Turi Becker.
408 reviews28 followers
November 30, 2009
I've read a few crossword books in the past couple of years (although I haven't really been doing puzzles lately) and this one doesn't disappoint. A rambling, but always interesting look at puzzling's history and possible future, with a bit of focus on "cryptic crosswords."
225 reviews
December 29, 2009
A fun and quick read for puzzle dorks. Mostly a love-letter to the crossword puzzle and its elegance. That said, Olsher sometimes tends to get a little too dramatic and sentimental, especially when praising the cryptic crossword, which he does at great length.
Profile Image for Matt Kelly.
106 reviews2 followers
August 5, 2016
I really wanted to like this book, but it was just a meandering stream of consciousness about crosswords. Fully a third of the book is spent trying to convince the reader how great cryptic crosswords are, but as I already solve cryptics, this was not really useful to me.
Profile Image for Phillip.
2 reviews91 followers
Currently reading
May 14, 2009
so far, brilliantly written to mimic the feel and philosophy of a crossword puzzle.
129 reviews1 follower
October 13, 2009
Subtitled, "A Meditation, with Digressions, on Crosswords." Well, maybe there's just not that much to say about crossword puzzles--some amusing digressions, though.
436 reviews16 followers
March 13, 2012
There's a lot not to like in this book, but any crossword enthusiast will probably enjoy it.
139 reviews10 followers
April 8, 2010
Lots of fun. Informative about different crossword constructors and ways clues are developed.
469 reviews
June 1, 2010
I adored this -- like a long, very good radio programme on crosswords. And it taught me how to do cryptic crosswords, which I have always wanted to learn! Probably not for everyone, though.
Profile Image for Cynthia.
290 reviews4 followers
November 2, 2013
Memoir of the joys of crossword puzzles, including history, lore, and addictive qualities.
Displaying 1 - 30 of 32 reviews

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