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彼の性格が読めてきたような気がしないでもなかった

しない is a negative conjugation of する

And from what I understand でもなかった is the equivalent of "was not"

So it's a double denial? How does this work?

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Yes, しないでもない (≒しなくもない) is a double-negative construction, which can be seen as a set phrase used to say something less confidently, or to reluctantly admit something.

彼の性格が読めてきたような気がしないでもなかった
(lit.) It was not that I didn't feel I came to be able to read his character.
I feel I have gradually learnt how to understand his character.

Similar examples:

  • 失敗だったと言えなくもない。 ≒ 失敗だったと言えないでもない。
    (lit.) It is not that one cannot say it was a failure.
    One could argue that it was a failure.
  • 100万円はなくもない。 ≒ 100万円はないでもない。
    (lit.) It is not that I don't have one million yen.
    (Admittedly,) I have one million yen.

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