Droplet interface bilayers are a convenient model system to study the physio-chemical properties of phospholipid bilayers, the major component of the cell membrane. The mechanical response of these bilayers to various external mechanical stimuli is an active area of research due to implications for cellular viability and development of artificial cells. In this manuscript we characterize the separation mechanics of droplet interface bilayers under step strain using a combination of experiments and numerical modeling. Initially, we show that the bilayer surface energy can be obtained using principles of energy conservation. Subsequently, we subject the system to a step strain by separating the drops in a step wise manner, and track the evolution of the bilayer contact angle and radius. The relaxation time of the bilayer contact angle and radius, along with the decay magnitude of the bilayer radius were observed to increase with each separation step. By analyzing the forces acting on the bilayer and the rate of separation, we show that the bilayer separates primarily through the peeling process with the dominant resistance to separation coming from viscous dissipation associated with corner flows. Finally, we explain the intrinsic features of the observed bilayer separation by means of a mathematical model comprising of the Young-Laplace equation and an evolution equation. We believe that the reported experimental and numerical results extend the scientific understanding of lipid bilayer mechanics, and that the developed experimental and numerical tools offer a convenient platform to study the mechanics of other types of bilayers.