Is it correct to say, "He is too careless not to make such a mistake," when I mean he is so careless that he made such a mistake?

Thank you very much.

  • Please could you give some more context that explains why someone would want to say that? It's grammatically OK, but it sounds as if someone has found that a mistake was made, and wants to blame it on someone else for no better reason than that the second person is careless. – Rosie F Jul 18 at 5:42
  • Thank you. I am not sure if the "too ... not to" expression is suitable for describing a cause-effect relationship. I meant to say, "He is careless, so he made the mistake." – Kevin Jul 18 at 6:12
  • There's a bit of a double negative feel to this that makes it harder to understand. To me its says: he has a past history of being careless so it's inevitable that he will have made this particular mistake. Is that what you intended to say? – Mynamite Jul 18 at 11:03
  • Thank you. I meant to say, "It is because he is always careless that he made such a mistake." – Kevin Jul 18 at 12:15
  • I have never heard this negated expression before, and it took me a few seconds to parse it. Far more common is he is too careful to make a mistake. But while I find this negative version somewhat bizarre (because I've never encountered it before), there is nothing actually wrong with it. In a positive way, even this would sound more natural: He is too careless to do it right. – Jason Bassford Jul 18 at 21:20

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