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I would like to say: "He never comes to Osaka (no matter what)"

彼は決して大阪に行かない。

To express the "never" part, I know there are words like 決して、絶対に、全然、全く, but which sound more natural to the Japanese ear when spoken and when written? And are there other words to express this as well?

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If saying "no matter what" is important, 絶対に is the most natural option in speech. Both 絶対に and 決して will work fine in written text, but the latter would sound a bit more formal. This is one of the exceptions where a kango version sounds less formal. Other idiomatic options include:

全然 and 全く just mean "at all", but they do not mean "no matter what." They are often used for something you can count or measure. In this context, using 全く/全然 would imply he is expected to go to Osaka on a regular basis, but don't do so even once.

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"He never comes to Osaka (no matter what)"

どれがnaturalかは状況に応じますので明確に言えません。
以下の( )の中に、各々に対して私の感じを書きますので参考にしてください。

  1. 彼は決して大阪に行かない。(本人の意志が固い。客観的に見て行かない理由もなんとなく分かる。2より上品な/穏やかな表現)
  2. 彼は絶対に大阪に行かない。(本人の意志が固い)
  3. 彼は全然大阪に行かない。(客観的に見て行く気配がない)
  4. 彼は全く大阪に行かない。(客観的に見て行く気配がない。3より上品な/穏やかな表現)
  5. 彼は頑として大阪に行かない。(本人の意志が1,2より固い)

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