Have you ever used an everyday phrase and stopped for a moment to think Wait, that doesn’t actually make sense? You will probably be right, since it turns out English is full of sayings that fall apart the moment you look them in the eye. You might be talking ten to the dozen, complaining that someone wants to have their cake and eat it, considering something to be cheap at half the price, or even feeling lucky enough to have fallen head over heels. Each of these is illogical in its own way. So how exactly have they survived this long?
The immediate answer is that they didn’t always look this way. The originals, when they first appeared, were far more straightforward. Take ‘to have one’s cake and eat it’, which sounds like a perfectly normal series of events: why else would we buy cake if not to enjoy it? But all becomes clear when you learn the earliest wording of this proverb, recorded in a collection of sayings from the 16th century: ‘Wolde ye bothe eate your cake, and haue your cake?’. This was later enshrined in English as ‘You can’t eat your cake and have it too’: illustrating the truth that you never can have everything in life. In this version the trouble isn’t in the eating: it’s the keeping of it that is the tricky part, which makes much more sense if you’re partial to a Victoria sponge.
‘Head over heels’ describes falling headlong into love and infatuation. It’s a lovely image, until you realise that we actually spend most of our lives with our head above our heels, so what’s so upending about that? Take a look at the historical dictionary and you’ll see that the earliest mention of the phrase, in the Middle Ages, was ‘heels over head’, which is much more evocative of doing an emotional somersault.

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