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I'm kind of beginner so maybe I'm wrong, but I understand it as "The LATAM sky sadly blue" but I don't really get the meaning behind the words. Since Japanese language is a lot about context, I will publish the whole sentence.

街並みがあまりにもヨーロッパに似ているのも、それなのにくっきりと濃い、南米特有の悲しいほど青い空に、ジャカランダの木が枝を伸ばしているのも、新鮮だった。

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  • ほど is used for comparison in this case. 悲しいほど青い空 means "sky so blue that it is sad"
    – andrewb
    Jun 21 at 15:06
  • Thank you @andrewb , I didn't know this usage of ほど. I thought it could be an expression but at the end it's just the image that we have of the color blue
    – Ryu
    Jun 21 at 15:17
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    Note that 悲【かな】しい doesn't just mean "sad" -- the underlying meaning is more like "moving, emotionally affecting". C.f. the intro to the entry in the 広辞苑【こうじえん】 dictionary: 「自分【じぶん】の力【ちから】ではとても及【およ】ばないと感【かん】じる切【せつ】なさをいう語【ご】。悲哀【ひあい】にも愛憐【あいれん】にも感情【かんじょう】の切【せつ】ないことをいう。」 ("Word expressing a kind of heartrending-ness/deeply moving-ness that feels beyond one's own power. Indicates the heartrending/deeply moving sense of emotion in both sadness and compassion/pity.") Jun 21 at 18:33
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    Thank you for the details on the definition of 悲しい @EiríkrÚtlendi
    – Ryu
    Jun 22 at 15:50

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It basically means the writer (or the character in focus) is being overwhelmed or upset at something, "the blue sky" in this case. I think there often is a certain sense of conflicted emotion with this 悲しいほどに, like "I should like it but this is too much", when used with normally positive concepts. It's also a bit unusual, poetic expression. You are more likely to see it in songs and novels, than in daily conversation and a (non-artistic) professional setting. If I were to translate it, I might choose "disturbingly" or maybe "overwhelmingly" rather than something that involves "sadness".

悲しいほどに美しい is another typical phrase that uses 悲しいほど in this sense. It can be used to describe an ephemeral/stoic kind of beauty, rather than one that (merely) provokes pleasure.

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  • Oh wow, I can't up vote your answer at the moment because my account is new, but thank you for this enlightenment. And I can see it now that you've mentioned it, I suppose she's kind of upset because people in town are white, building very European and yet this blue sky is South American. 教えてありがとうございました。
    – Ryu
    Jun 23 at 22:54

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