An auto-antonym (or, more properly, autantonym), or contronym (sometimes misspelled contranym) is a word with a homograph that is also an antonym. Variant names include antagonym, Janus word, and self-antonym. It is a word with multiple meanings, one of which is defined as the reverse of one of its other meanings.

For example, the word "fast" can mean "moving quickly" as in "running fast," or it can mean "not moving" as in "stuck fast." To buckle can mean "to fasten" when used transitively or "to bend then break" intransitively. To weather can mean "to endure" (intransitive) or "to erode" (transitive). "Out" can mean both shining, as in "The stars are out tonight," or it can mean the opposite, as in "Please turn out the lights." Weedy can mean overgrown (the garden is weedy) or stunted (he is weedy). To overlook can mean "to inspect" or "to fail to notice." This phenomenon is also called "enantionymy" or "antilogy."

The terms "autantonym" and "contronym" were originally coined by Joseph T. Shipley in 1960 and Jack Herring in 1962, respectively. A related term, pseudo-contronym, was coined by David Morice in 1987.

Some pairs of contronyms are true homographs, i.e., distinct words with different etymology which happen to have the same form. For instance cleave "separate" is from Old English clēofen, while cleave "adhere" is from Old English cleofian, which was pronounced differently. Other examples include let — "hinder" (as in tennis) or "allow". This is related to false friends, but false friends do not necessarily contradict.

Other contronyms result from polysemy, where a single word acquires different, and ultimately opposite, senses. For instance quite, which meant "clear" or "free" in Middle English, can mean "slightly" (quite nice) or "completely" (quite beautiful). Other examples include sanction — "permit" or "penalize"; bolt (originally from crossbows) — "leave quickly" or "fixed"; fast — "moving rapidly" or "unmoving". Many English examples result from nouns being verbalized into distinct senses "add to" and "remove from"; e.g. dust, seed, stone. Some contranyms result from differences in national varieties of English; for example, to table a bill means to put it up for debate in British English but means to remove it from debate in American English.

Often, one sense is more obscure or archaic, increasing the danger of misinterpretation when it does occur; for instance, the King James Bible often uses "let" in the sense of "forbid."

An apocryphal story relates how an English monarch described St Paul's Cathedral as "awful, artificial and amusing", meaning "awesome, clever and thought-provoking."

Auto-antonyms also exist in other languages. For example, in French hôte may mean either "host" or "guest", and in Hindi कल (kal, kʌl) may mean either "yesterday" or "tomorrow" (disambiguated by the verb in the sentence).

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