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In chapter 6 of Alice’s Adventure’s in Wonderland the enigmatic Cheshire cat makes an appearance and the oft-quoted exchange takes place:

Would you tell me, please, which way I ought to go from here?”

“That depends a good deal on where you want to get to,” said the Cat.

“I don’t much care where ―” said Alice.

“Then it doesn’t matter which way you go,” said the Cat.

They talk on for a little while and then the Cat vanishes

beginning with the end of the tail, and ending with the grin, which remained some time after the rest of it had gone.”

It’s very tempting to think that the Cheshire cat is Lewis Carroll’s invention but it’s not. The phrase to grin like a Cheshire cat (=to have a broad smile on your face) was already in use towards the end of the 18th century.

As you may know, the English county of Cheshire is famous for its cheeses, and it’s said that in the past they were either made in the shape of a cat or had the head of a cat stamped on them.

Another story goes that a Cheshire sign painter was commissioned by a local noble family to depict their coat of arms featuring the lion rampant. However, whether due to lack of talent or inspiration, the results of his labours looked like a grinning cat rather than a roaring lion, much to everyone’s amusement.

Alternatively, the phrase may owe its origins to a Cheshire gamekeeper of King Richard III. His name was Caterling and he found great pleasure in seeing poachers being hanged, which would bring a nasty grin onto his face. Originally people would say to grin like a Cheshire Caterling but over time Caterling was shortened to cat.

Did any of these stories make you grin like a Cheshire cat? Let me know!

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