A pressure-sensitive film was used to characterize the asperity contacts along a polymethyl methacrylate (PMMA) interface in the laboratory. The film has structural health monitoring (SHM) applications for flanges and other precision fittings and train rail condition monitoring. To calibrate the film, simple spherical indentation tests were performed and validated against a finite element model (FEM) to compare normal stress profiles. Experimental measurements of the normal stress profiles were within −7.7% to 6.6% of the numerical calculations between 12 and 50 MPa asperity normal stress. The film also possessed the capability of quantifying surface roughness, an important parameter when examining wear and attrition in SHM applications. A high definition video camera supplied data for photometric analysis (i.e., the measure of visible light) of asperities along the PMMA-PMMA interface in a direct shear configuration, taking advantage of the transparent nature of the sample material. Normal stress over individual asperities, calculated with the pressure-sensitive film, was compared to the light intensity transmitted through the interface. We found that the luminous intensity transmitted through individual asperities linearly increased 0.05643 ± 0.0012 candelas for an increase of 1 MPa in normal stress between normal stresses ranging from 23 to 33 MPa.