So as I said in the title- I'm talking about the covariance of $X$ and $Y$.
Also, is it correct to say that if I know that $Y>0$ iff $X>0$, and also $Y<0$ iff $X<0$ then $\operatorname{cov}(X,Y)>0$?
It makes sense to me but I just can't see it by the definition of covariance.
This is certainly true when the expected values of $X$ and $Y$ are both $0$, as is easily verified.
Now consider $\{(-1,-1)\} \cup \{ (j,1000-j) : j=1,\ldots,1000\}.$ Software is telling me the correlation is $-0.9939881.$ Look at the graph.