The synergistic effect of surface texturing and lubricants with various viscosity and polarity properties is an attractive and unexplored topic. In this study, surface texturing characterized by circular dimples has been manufactured on steel surfaces in advance, which can improve the lubrication of frictional units compared with the bare disc under different lubricants. Then, three lubricants, low-viscosity and nonpolar white oil, high viscosity and nonpolar silicone oil, and highly viscous and polar castor oil, were used to evaluate the interaction between surface texture and the lubricating oil. The contact angles of each lubricant on the textured and bare surface were measured to investigate the lubricant intermolecular force and wettability. The oil film thickness simulation and tribological experiments were conducted. The tribological results indicate that lubricants with varied characteristics work differently due to their different properties on textured surfaces. Castor oil exhibits the best tribological properties of the three oils used to supply the textured surfaces, which may attribute to its ability to generate strong boundary adsorption films as well as a thickened interfacial layer, and it could reduce the intensity of asperity interaction.