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Does 懐かしむ suffice? Can it convey the sadness of losing someone close to you? If not, how would one express such a thing?

I'm having trouble dealing with this, as there are plenty of uses "miss" in English that carry wildly different levels of emotion, and I'm not sure if this variability carries over to Japanese.

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No, 懐かしむ is about feeling nostalgic, but not about feeling sad or lonely. Just as any dictionary says, this type of "miss" is usually translated as 寂しい, 寂しく思う, etc.

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