Breaking Down Woebegone

At first glance, woebegone looks like a word that has its meaning backwards; after all, if begone means "to go away," shouldn't woebegone mean "devoid of woe," or "happy"? Not exactly. The word derives from the Middle English phrase wo begon. The wo in this phrase simply means "woe," but begon (deriving from Old English began) is a past participle meaning "beset." Someone who is woebegone, therefore, is beset with woe. Since the early 19th century, the word has also been used to describe things that appear to express sadness, as in "a woebegone face."