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There is a question on here asking why women is pronounced 'wimen', but what intrigues me is why is it spelled with an 'o'?

If wi was the original pronunciation for both singular and plural, why weren't both words spelled wiman/wimen?

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The original spelling "wifman" evolved during the centuries to "woman" but "the pronunciation of the singular altered in Middle English by the rounding influence of -w-; the plural retains the original vowel" (etymonline).

  • The spelling of woman in English has progressed over the past millennium from wīfmann to wīmmann to wumman, and finally, the modern spelling woman. In Old English, wīfmann meant "female human", whereas wēr meant "male human". Mann or monn had a gender-neutral meaning of "human", corresponding to Modern English "person" or "someone"; however, subsequent to the Norman Conquest, man began to be used more in reference to "male human", and by the late 13th century had begun to eclipse usage of the older term wēr. The medial labial consonants f and m in wīfmann coalesced into the modern form "woman", while the initial element, which meant "female", underwent semantic narrowing to the sense of a married woman ("wife").

  • It is a popular misconception that the term "woman" is etymologically connected to "womb". "Womb" is actually from the Old English word wambe meaning "stomach" (modern German retains the colloquial term "Wampe" from Middle High German for "potbelly").

Wikipedia

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  • Josh, do you not think “wifman” originally meant “weaving person” or “one who weaves” and morphed into “wife” in the same way that “husbandman” meant “husbanding person” or “one who husbands” and then morphed into “husband” even though “husbandman” also retains its original meaning? Nov 27, 2016 at 22:13

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