Q From Eddie Sng: I’d like to know how the phrase head over heels came about, as in, ‘I’ve fallen head over heels in love with you’.
A That’s pretty much a set phrase these days, so that to be head over heels almost always means that one has fallen madly in love in an impetuous and unconstrained way. But by itself it can also refer to one’s state while turning a somersault or cartwheel. It’s more than a little weird when you think about it — what’s so strange about having one’s head over one’s heels? After all, we do spend most of our waking lives in that position.
It looks so odd because during its history it got turned upside down, just like the idea it represents. When it first appeared, back in the fourteenth century, it was written as heels over head, which makes a lot more sense. Logically, it meant to be upside down, or, as to turn heels over head, to turn a somersault.
It became inverted around the end of the eighteenth century, it seems as the result of a series of mistakes by authors who didn’t stop to think about the conventional phrase they were writing. The two forms lived alongside each other for most of the next century — the famous Davy Crockett was an early user of the modern form in 1834: “I soon found myself head over heels in love with this girl”, but as late as the beginning of the twentieth century L Frank Baum consistently used the older form in his Oz books: “But suddenly he came flying from the nearest mountain and tumbled heels over head beside them”. And Lucy Maud Montgomery stayed with it in her Anne of Windy Poplars, published as late as 1936: “Gerald’s pole, which he had stuck rather deep in the mud, came away with unexpected ease at his third tug and Gerald promptly shot heels over head backward into the water”.