Although the there are several definitions in the dictionary:

  * my condolences
  * that's too bad
  * my sympathies

What does お気の毒に literally mean? I'm guessing that it might have something to
do with "poisoned ki".

After checking the dictionary, this phrase seems to be said to someone who has
had a death in their family. Is it also used in other situations, such as:

  * To someone who has a family member with a terminal illness (cancer), just diagnosed with cancer, living with cancer, dementia, parkinson's, etc?

  * Said directly to the person who has the disease or debilitating condition?
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2011-12-28T03:05:52.547
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2011-12-29T05:11:54.423
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meaning idioms metaphor
What is the meaning of お気の毒に and how is it used?
The literal meaning of the phrase is 'poisonous for your mind'. I think you
are trying to literary understand the `毒` 'poison' part, but that is just a
metaphor. The expression is not limited to medical situations. It means
'unfortunate' and is used generally.
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2011-12-28T03:28:42.193
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This was an interesting question. I see this in movie subtitles all the time
when the English line is along the lines of, "sorry for your loss."

The "best answer" on this provides some more insight to the answer already
given: <http://detail.chiebukuro.yahoo.co.jp/qa/question_detail/q119850871>
But the answer below that, where the guy talks about the origin in 江戸時代 is
also interesting. Basically in summary between the two posts, it's the
opposite of 気の薬, which in Edo times was something given to the sickly. I'd be
curious to know just WHAT 気の薬 was (a drink? a food? a pill?). Since it was
something good and given to cure sickness, poison (the opposite of medicine)
was used to express something bad such as 不安 or 困ること. And today it's used to
express sympathizing with someone for their loss.

To be honest, I still felt pretty unsatisfied with the answer, so I asked my
fiancee (Japanese) just now, what the origin and original meaning of お気の毒に is,
and she had no idea beyond that it's just a set phrase you say when to express
sympathy for someone's loss.

To address your question about other uses, she was able to say that you indeed
can say it to sick people expressing sympathy for their condition, IF the
condition is light/curable/will get better soon. She said that you can't
really say it to someone with a terminal or debilitating illness, because then
it's kind of just reminding them of the crappy situation they're in. Whereas
if someone breaks a bone or has a cold, well, they'll get better, and they're
just down and out temporarily, so it's kind of like, "dang, that sucks that
you got sick." Example sentence that I vaguely remember being told one time by
a Japanese co-worker a few years ago: お気の毒に…こんな忙しい時期に風邪を引いちゃうって、最悪だね,
expressing sympathy for the fact that I was sick, but I had my plate full and
had to continue working anyway.

It can also be used somewhat sarcastically, but it's not that common. It will
generally draw a chuckle if you use it for something like say, a close friend
(definitely not a co-worker or someone you don't really know) lost their phone
because it was their own fault/they were being a drunken idiot/etc.
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