This paper presents findings from a study conducted to evaluate changes in the microstructure of asphalt binder resulting from aging as well as the effect of these changes on the evolution of damage resulting from tensile deformations. Two types of asphalt binders were aged with the rolling thin film oven and pressure aging vessel aging techniques. The microstructure and the microrheology of the six binders were obtained with atomic force microscopy (AFM) imaging and creep indentation experiments. This information was then used to perform numerical simulations to examine the effect of tensile strains on the internal stress distribution in the binder. Experimentally, a microloading apparatus was used to induce tensile strains in the samples of the asphalt binder while the binder was observed for damage with the use of AFM. The damage and changes in the binder microstructure resulting from the tensile load observed experimentally were compared with the results from the numerical simulations. Results suggest that localized regions of high stress intensity between different domains act as damage nucleation sites. Results also suggest that the differences in the rheological properties of the microdomains reduce with aging. As a result, the internal distribution of stresses becomes less heterogeneous, the magnitude of stress localization decreases, and there are fewer sites where damage nucleates.