Significant information about the topology of a bounded domain $\Omega$ of a Riemannian manifold $M$ is encoded into the properties of the distance, $d_{\partial \Omega }$, from the boundary of $\Omega$. We discuss recent results showing the invariance of the singular set of the distance function with respect to the generalized gradient flow of $d_{\partial \Omega }$, as well as applications to homotopy equivalence.