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An interesting paradox occurs when a word evolves to become its own antonym. How does this happen?
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You can see a list of contronyms (antagonyms) gathered here.  The website hyperlinked describes this as “some freak of language evolution,” but I am hoping to find a more precise explanation in this forum.  Examples from the linked website provided include:

  • anabasis – military advance, military retreat
  • apology – admission of fault in what you think, say, or do; formal defense of what you think, say, or do
  • aught – all, nothing
  • bolt – secure, run away
  • by – multiplication (e.g., a three by five matrix), division (e.g., dividing eight by four)
  • chuffed – pleased, annoyed
  • cleave – separate, adhere
  • clip – fasten, detach
  • consult – ask for advice, give advice
  • copemate – partner, antagonist
  • custom – usual, special
  • deceptively smart – smarter than one appears, dumber than one appears
  • dike – wall, ditch
  • discursive – proceeding coherently from topic to topic, moving aimlessly from topic to topic
  • dollop – a large amount, a small amount
  • dust – add fine particles, remove fine particles
  • enjoin – prescribe, prohibit
  • fast – quick, unmoving
  • first degree – most severe (e.g., murder), least severe (e.g., burn)
  • fix – restore, castrate
  • flog – criticize harshly, promote aggressively
  • garnish – enhance (e.g., food), curtail (e.g., wages)
  • give out – produce, stop production
  • grade – incline, level
  • handicap – advantage, disadvantage
  • help – assist, prevent (e.g., “I can’t help it if…”)
  • left – remaining, departed from
  • liege – sovereign lord, loyal subject
  • mean – average, excellent (e.g., “plays a mean game”)
  • off – off, on (e.g., “the alarm went off”)
  • out – visible (e.g., stars), invisible (e.g., lights)
  • out of – outside, inside (e.g., “work out of one’s home”)
  • oversight – error, care
  • pitted – with the pit in, with the pit removed
  • put out – extinguish, generate (e.g., something putting out light)
  • quiddity – essence, trifling point
  • quite – rather, completely
  • ravel – tangle, disentangle
  • rent – buy use of, sell use of
  • rinky-dink – insignificant, one who frequents
  • sanction – approve, boycott
  • sanguine – hopeful, murderous (obsolete synonym for “sanguinary”)
  • screen – show, hide
  • seed – add seeds (e.g., “to seed a field”), remove seeds (e.g., “to seed a tomato”)
  • skinned – with the skin on, with the skin removed
  • strike – hit, miss (in baseball)
  • table – propose (in the United Kingdom), set aside (in the United States)
  • transparent – invisible, obvious
  • unbending – rigid, relaxing
  • variety – one type (e.g., “this variety”), many types (e.g., “a variety”)
  • wear – endure through use, decay through use
  • weather – withstand, wear away
  • wind up – end, start up (e.g., a watch)
  • with – alongside, against
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Welcome to the forum PacificJD. There’s another thread on this topic here, along with some other links.

To answer your question, we’d need an etymologist to weigh in (which I’m not). But there’s plenty of them around AWWW and maybe they can provide some clues. Would be nice to have Grant drop by and address your question, but I haven’t seem him much around here lately.

That said, I wouldn’t so much call it a “paradox” … more like just a linguistic curiosity, imho. Probably happens in other languages too. Every contronym probably has its own interesting origins. I note that many examples (weather, clip, seed) seem to come from “verbified” nouns, so, for example, whether one is attaching something with a clip, or removing something that was clipped, the ambiguity arose naturally to avoid the need for a whole new word. Sure, we have detach” as a synonym for “clip,” but I think a lot of usage just derives from expediency.

Adjective contronyms like “transparent” are a bit harder to fathom. Likewise verb contronyms like “table.”

Not sure if this helped much, but it’s the best I can do. You might find some clues here:  http://www.etymonline.com/

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Yet is not yet:

A fifth limb yet named.

A fifth limb not yet named.