We study questions of stability of two types of singularities encountered in geometric evolutionary PDE, one in Ricci flow and the other in the context of the Einstein field equations in vacuum. In the first part of the thesis we introduce certain spherically symmetric singular Ricci solitons and study their stability under the Ricci flow from a dynamical PDE point of view. The solitons in question exist for all dimensions $n+1\ge 3$, and all have a point singularity where the curvature blows up; their evolution under the Ricci flow is in sharp contrast to the evolution of their smooth counterparts. In particular, the family of diffeomorphisms associated with the Ricci flow ``pushes away'' from the singularity causing the evolving soliton...