These are dramatically philosophical, but also dispatched by epistemologists for a long time now. 1. "Isn't its very meaninglessness its meaning" is a confusio

These are dramatically philosophical, but also dispatched by epistemologists for a long time now. 1. "Isn't its very meaninglessness its meaning" is a confusion of reference and sense. The quoted sentence "Colorless green ideals sleep furiously" interpreted as an object in its own right holds meaning as a common example of syntax and semantics but if you "remove the quotes" and interpret its sense then we run into problems... and obviously that's what everyone is talking about when they bring it up. 2. "Is it in this way that it fails to have meaning and so will always continue to fail to have meaning?" Yep. If we assert that we're stating this sentence as an assertion or judgement of reality then we would like to evaluate its "truth". Even without getting too mystical it's a long established sense of the definition of truth that it ought to somehow correspond with reality and that any notion of truth which does not is hypothetical or meaningless. This is encapsulated in Dummett's C and discussed by Per Martin-Löf here: https://michaelt.github.io/martin-lof/Truth-and-Knowability-On-the-Principles-C-and-K-of-Michael-Dummett-1998.pdf https://michaelt.github.io/martin-lof/Truth-and-Knowability-...