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it also doesn't care if i define a fake TYPE_CHECKING variable
I think that's probably a remnant of when you couldn't import TYPE_CHECKING (or MYPY, which was an earlier version of the same thing) from typing so defining a False constant with the right name was the recommended usage (see the first example in #308).
That behavior could be considered a feature if you wanted to be able to add types to Python 2 code without having to install the typing backport, but, judging from #12237, we're probably fine making breaking changes for Python 2 users.
playground
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