Recently I bumped into two words「断り」and「惜しい」.

  • Accordingly to Jisho:「断り」can mean permission; consent​ but it also can mean rejection; refusal; nonacceptance; declination; declining​...
  • As for「惜しい」 it can mean regrettable; disappointing; unfortunate​ or also precious; dear; valuable​...

Of course, in the case of 「惜しい」 these meanings are not exact opposite but still one conveys a positive connotation and the other a negative. I'm aware that any language has some words with polar meanings.

My question is, besides context, in Japanese is there a rule of thumb that one could use to identify if the connotation is positive or negative?

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