Nobody started it. It’s a natural language development to shorten people’s names in familiar contexts.
Some English names are very old, and have had a lot of time to go through various changes. Pronunciation of English has also changed at the same time, leaving remnants in some of these names. That’s how we got Richard -> Rich -> Rick -> Dick.
Chuck is a term of endearment (e.g. like “babe” or “dude”) in parts of England, and was incorrectly assumed to be a shortening of Charles at some point in 19th Century America.
Jimmy means “little James”, from Hebrew, and that was shortened to just Jim.
From my understanding it was common to have a lot of people with the same name. So that you needed nicknames to separate them out. off of it was just a diminutive form but then they are going to rhyming to expand the number.
Robert was a common name. Robert, Robbie, Robby, Robin, Rob, Bob, Bobby, Nob, Nobin, Hob, Hobbes.
My name is Richard. I’m 85 years old. I’m named after an uncle, who was always called “Dick.” When I was little I was called “Dickie.” As I got bigger this transitioned to “Dick,” which persisted into my late 50s, early 60s. Then I noticed that people more than 20 years younger than I were uncomfortable with my nickname. They called me “Richard.“ It’s what everybody calls me now.
Seventy years ago “Dick“ had already begun to be slang for “penis.” The latter was rarely used. There were slang equivalents at least as common as my nickname, if not moreso. If people tried to make a joke of my nickname, I told them they could say it with a straight face. At sixteen I was six feet, four inches, and weighed 195 lbs, big for 1953.
Nowadays my nickname not only denotes the male organ, for years it has been an insult.
My fanciful story of the shift in meaning is that it originated in the Tudor English monarchs’ efforts to blacken the reputation of their predecessor, hunchback Richard III. There is an old ballad, “Crooked Dick, the bastard King of England.”
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