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Q From John David Hamilton, Ontario, Canada: I have long been puzzled by the fact that woebegone is used in a sense opposite to what the word seemingly means. I grew up with the expression ‘a woebegone face’ meaning a sad, woeful, unhappy face. But if you take the word as it is spelled, it should mean ‘a happy, cheerful, optimistic face full of determined good cheer’. Why is this (and why does the dictionary give the contradictory meaning)?

A It does look as though it’s from a wish or desire: “let woe be gone”. But the story is rather more complicated, and to answer it, we have to delve into medieval English.

Woebegone is first recorded in The Romance of Guy of Warwick, of about the year 1300. At that date, people would say things like “me is woe begon”, grief has beset me. Notice the word order, with me as the indirect object of the sentence, but put first. The verb here is bego, which has been obsolete for something like four hundred years, but which in medieval times had a variety of senses, such as to go round, surround or beset.

Over time, the link between woe and begone, the past participle of bego, became so close that they fused into a single adjective, so tightly linked that they survived shifts in language and the loss of the verb bego.

For some centuries it retained this sense of “afflicted by grief”, oppressed with misfortune, distress, sorrow or grief. Shakespeare uses it this way in Henry IV:

Even such a man, so faint, so spiritless,
So dull, so dread in look, so woe-begone,
Drew Priam’s curtain in the dead of night
And would have told him half his Troy was burnt.

This quotation in particular was so well known that it contributed to a revival of woebegone in a subtly altered sense at the beginning of the nineteenth century, not meaning somebody actually beset by woes, but somebody whose appearance makes them look as though they are.

We’re now a long way from that medieval romance, but in continuing to use the word we retain a small vestige of middle English as a linguistic fossil. Several other archaic forms in woe have also survived, such as “woe is me” and “woe betide you”, presumably because there’s a continuing need for formulaic lamentatory utterances.

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