To be woebegone is to be sad, forlorn, or heartbroken. The woebegone expression on your face tells everyone how totally bummed out you are.

The word woebegone doesn't make its meaning clear at first glance: it seems to imply that woe, or extreme sadness, is gone. This adjective actually stems from a Middle English phrase, wo begon, "beset or surrounded by woe." So if you see your friend looking upset or glum, you might want to ask, "Why so woebegone?"

Definitions of woebegone
  1. adjective
    affected by or full of grief or woe
    “"his sorrow...made him look...haggard and... woebegone"- George du Maurier”
    synonyms: woeful
    experiencing or marked by or expressing sorrow especially that associated with irreparable loss
  2. adjective
    worn and broken down by hard use
    “a woebegone old shack”
    synonyms: creaky, decrepit, derelict, flea-bitten, run-down
    affected by wear; damaged by long use
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