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HEAD OVER HEELS IN LOVE means to be madly, out of control in love; totally and hopelessly smitten.

"It's obvious that they're head over heels in love with each other."

Often used with "fall" to describe the beginning of a relationship: 

"They met at a nightclub and instantly fell head over heels for one another."

But think about it. Why "head over heels"? Shouldn't it be "heels over head" instead? After all, our head is normally over our heels. Let's start at the beginning though. 

"Now, I'm head over heels in love with Sandra."

When first coined, it referred exclusively to being temporarily the wrong way up, tumbling upside down, head first, topsy-turvy, topple up tail, ass over tea-kettle, ass over tit, bass-ackwards, base over apex, etc.

"She tripped and rolled head over heels down the hill."

Later it also started to mean at top speed, in great confusion or disorder, frantically, full tilt, full throttle, like mad, etc. 

"Hearing the noise in the dark, the children ran head over heels back home."

Probably that, in its turn, led further to mean "downright, completely, thoroughly, deeply, utterly, etc.," in common use, departing its literal meaning.

"He was head over heels in debt."

The first mention of love comes after the time that the phrase had crossed the Atlantic. The lack of quotation marks or explanation in this example suggests that the expression was in common usage by that date:

"About ten years ago Lotta fell head over heels in love with a young Philadelphian of excellent family." [The Lebanon Patriot, Indiana, June 1833]

The most interesting fact is that the expression did originate in the 1300s as HEELS OVER HEAD which makes far more sense than "head over heels" when you think about the physics of a somersault. "Heels over head" is more literally accurate, as "head over heels" is the more standard state of being. That said, doesn't "head over heels" sound much better?

"I'm absolutely head over heels for you." 

"Heels over head" evolved into "head over heels" probably for reasons of pure phrasal elegance. Its long history of usage and abundance in pop culture as a title for numerous songs, albums, movies and books is a good example of how language can communicate meaning even when it makes no literal sense.

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