woebegone

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The Word of the Day for June 14 is:

woebegone   \WOH-bih-gahn\   adjective
     1 : strongly afflicted with woe : woeful
    *2 : exhibiting great woe, sorrow, or misery
     3 : being in a sorry state

Example sentence:
     Jerry's face had the woebegone expression of a man who had just lost a 
beloved pet.

Did you know?
     At first glance, "woebegone" looks like a word that has its meaning 
backwards; after all, if "begone" means "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 literally 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."

*Indicates the sense illustrated in the example sentence.