I remember when I was part of the dating scene, all those decades ago, some guy once saying that the word pretty was outdated, that no one called girls pretty anymore. I don’t know if he was right or not, but at least one contributor to Urbandictionary puts a fairly high value on the word pretty explaining that when a guy says a girl is pretty it means he really likes her, while if he says she’s hot, he’s actually less likely to really want to date her. I don’t know if that’s true either but lots of other Urbandictionary users seem to agree.

The word itself appeared first back in Old English and way back then (some years before I was part of the dating scene) it meant something quite different than our current understanding. The word is an evolution of the word prat and the Old English meaning of prat is “trick.” You can still find that word as part of our more modern word pratfall, which is a “trick fall” done by an actor. So someone that was pretty was someone who was “tricky” and the actual Oxford English Dictionary definition for the oldest meaning of the word pretty is “cunning” and “crafty.”

By the middle of the 1400s it had changed its meaning to closer to that we recognize now. Between the two, the “tricky” softened to “clever” and “skillful” and undoubtedly these are more attractive and so lead to pretty meaning “attractive.”

So the scene was set for that famous diary writer of the late 1600s Samuel Pepys to call a certain actress turned royal mistress “pretty, witty Nell.”

Nell Gwyn must have had some of the tricky elements of pretty in her as well as the clever and accomplished, besides the physically attractive, because hers is the classic rags to riches story. Her mom ran a house of ill repute and as a little girl Nell plied the customers with brandy. As a young woman her older sister got her a job selling oranges in a theatre from where she graduated to being an actress. She climbed the social ranks on the arms of various, ever increasing aristocratically elevated men until she could climb no higher because her final boyfriend was Charles II, King of England.

I guess one could say rags to riches or slept her way to the top but most people still say rags to riches because she remained very popular with the public despite her lowly beginnings and her dodgy pedigree at court. This even though she never learned to read or write. They say pretty is as pretty does.