It seems negative lookbehind expressions (which should be valid in both Ruby and JS flavors of regex, the latter as of ECMAScript 2018) don’t work in Watched Words.
Here’s an example:
(?<!new\s)\bcar\b should match instances of car that are not preceded by new.
E.g. it should match car in this sentence:
He drives a car
But not in this sentence:
He drives a new car
However, it returns the following error when adding under Watched Words:
Interestingly, it seems to be browser-dependent. I get the error in Safari, but not in Chrome. When adding it in Chrome and viewing the list in Safari the error shows up there.