Chemical, physical, and mechanical aspects determine the interaction between an adhesive and a substrate. In the case of pavement materials, where the binder acts as an adhesive and the aggregate acts as a substrate, a good interaction will depend to a large degree upon their chemical composition. For such a reason, the importance of the molecular interactions that take place on the surface of materials is recognized, because they define the quality of a forming interface. To analyze this topic deeper, this study explores the effect of manipulating the polarity of binders on their adhesion characteristics. Furthermore, the stripping potential (considered here as a combination of adhesion and debonding in the presence of water) was estimated by means of surface energy measurements. The findings suggest that it is possible to enhance the binder-aggregate interfaces by means of modifying their dispersive and polar components. The results in this study intent to help design binder-aggregate pairs with improved adhesion and water-resistance characteristics.