We aim in this manuscript to describe a specific notion of geometric positivity that manifests in cohomology rings associated to the flag variety $G/B$ and, in some cases, to subvarieties of $G/B$. We offer an exposition on the the well-known geometric basis of the homology of $G/B$ provided by Schubert varieties, whose dual basis in cohomology has nonnegative structure constants. In recent work [22] we showed that the equivariant cohomology of Peterson varieties satisfies a positivity phenomenon similar to that for Schubert calculus for $G/B$. Here we explain how this positivity extends to this particular nilpotent Hessenberg variety, and offer some open questions about the ingredients for extending positivity results to other Hessenberg varieties.