Where does woe is me come from?
English speakers have been using the phrase woe is me since Old English. The phrase notably appears in Shakespeare and in several editions of the Bible.
To many modern ears, woe is me may sound ungrammatical. Former New York Times Book Review editor Patricia T. O'Conner even published a book about grammar called Woe is I, mocking pedantic hyper-corrections that mistakenly hold woe is me should be woe is I.
The phrase woe is me, however, preserves an old dative case in English, and so literally means something more like "Woe is to me," that is, "I am distressed or afflicted." While English lost its dative case, woe is me has survived as a stock phrase in English, though its antiquated-sounding form has largely lent it to humorous hyperbole.
Google searches for woe is me mostly center around the alternative rock band Woe, Is Me. Searches for the phrase spiked in September, 2011 when the band announced a new lineup and again in November, 2012 when they released a new album.
Who uses woe is me?
The connotation of the phrase woe is me changes most notably depending on whether the speaker is directing the expression at themselves or at someone else.
When someone says woe is me about themselves, they are most likely using the phrase in a comical way. They might respond to an insignificant problem—if not highlight relative privilege and luxury—with woe is me as a playful overreaction. Someone could use woe is me in a similar way to "first world problems," (e.g., Should I get the black iPhone or the rose gold one? I can't pick. Woe is me!). In some situations, woe is me can also be used to sarcastically belittle someone else's "misery" in a similar tongue-in-cheek way.
Saying that someone else has a woe-is-me attitude or personality is saying that they are too self-pitying, succumb to a negative situation, act like a victim, or expect success to be handed to them. Most speakers who attribute a woe-is-me attitude to someone else are using the phrase to disparage their perceived weakness or softness.
It's so annoying when guys play the "woe is me" because they're single; chances are they're the ones that ruined their own chances 😂😭
@Christina_Teeee, March, 2018
The “struggle” of the cruise life: taking a shower at around 4pm and deciding if I should get dressed for dinner early, or put on regular clothes for like an hour. Woe is me!
Matt Hochberg, Royal Caribbean Blog, March, 2018
Lack of self-control while trying to do things our own way causes us to miss the blessings that come from fully trusting in the lord. Then there comes the woe-is-me factor as if the lord is against you in some way. Now, here comes the pity party and lack of faith in that which you know is true.
Edith Nevis, Houma Today, March, 2018