Ducks in a row, sinking.
Dear Word Detective: I told my boss something was “squared away” and suddenly wondered where that phrase comes from, and why it’s a good thing for a person, in this case, thing, or situation to be squared away. I fussed around the internet and came away with three options: it means old fashioned as in “square” music; it refers to boxing or wrestling where opponents “square off” against each other, or it’s the dreaded “nautical term” meaning the sails are at right angles to the deck of a ship in relationship to wind direction (or some such) and therefore in good order. Sadly, I want it to be the nautical definition because I just don’t see how getting ready to get pounded to a pulp or twisted into a knot is a good idea. For that matter I don’t know how one sail position is better than another unless it just satisfies a sense of order, but there you go. That’s those nautical phrases for you. — Victoria Ayers.
Indeed. As a matter of fact, since we’re on the subject, I’ve often thought life would be much simpler if nothing floated. Absolutely nothing at all. If even a feather sank like a stone in water. I imagine ducks would hate it and some fish would be inconvenienced, but I think it would be worth it just for me to never have to type the phrase “of nautical origin” again. Plus which, I imagine the folks on the Titanic would have been much happier staying home: “Ocean voyage? How would that work? Don’t be silly! Smithers, fetch us more nachos.”
Oh well, I’ve just been informed of the appalling amount of paperwork it takes to modify a basic law of physics, so I guess I’ll stick to answering your question. Our English word “square” first appeared around 1300 as a noun meaning “an implement for determining right angles,” more or less what we would now call a “T-square.” We adapted our word “square” from the Old French “esquire,” which was based on the Latin “ex” (out) plus “quadrare,” make square (from “quadrus,” a square). The use of “square” to mean a geometric shape made of four right angles developed by the end of the 14th century, and a wide variety of other meanings (e.g., a number multiplied by itself) had developed by the 16th century. “Square” also came to mean “a standard or rule; a guiding principle,” in reference to those T-squares used to verify a proper right angle. A “square meal” is one that is nutritious and complete.
Incidentally, our modern English “esquire” is unrelated to that Old French “esquire.” Our “esquire” comes from the Old French “escuyer,” meaning “shield bearer,” an “esquire” originally being a knight’s assistant.
“Square” as a verb appeared in the late 14th century meaning simply “to make square,” but quickly acquired a wide range of figurative meanings. “Square” in the sense of “old fashioned” or “clueless” appeared as slang in the late 1940s, originally designating some geezer who didn’t “get” jazz. The term is said to have come from the rigid hand motions of an orchestra conductor keeping an un-cool traditional four-beat tempo. To “square off” comes from boxing and refers to a fighter adopting a wide stance with arms cocked in preparation for the start of a match.
Meanwhile back at the dreaded “nautical origin” possibility, as of the early 17th century “to square” meant to align the sails at right angles to the keel of a “square-rigged” sailing ship, the optimal arrangement (with the wind from aft, presumably). “Squaring” other parts of the ship’s rigging meant to put them in correct order and position. That would tend to suggest a nautical source of “squared away.” But “to square” had also come to be used to mean “to put in proper order, to reconcile, settle,” as we speak of “squaring” accounts by settling debts, balancing the books, etc. This usage clearly referred back to the use of the noun “square” to mean “guiding principle, proper order,” and had nothing to do with sailing ships.
In any case, the phrase “square away,” meaning “to put in proper order, to tidy up,” first appeared in print in 1909, in a notably non-nautical context (“She had a head on her, Barbie had, an’ when she got squared away, she made ‘em all get down an’ scratch”), and has been in wide use ever since. My sense is that while some people may think of sailing ships when they hear it, the phrase itself is more tied to the accounting use of “square” to mean “in proper order.”