The de-wetting process of Zdol-type lubricants on hard disks has been studied at the molecular scale with scanning polarization force microscopy (SPFM) and ellipsometry. It was found that de-wetting occurred over hours to days when the initial lubricant layer was thicker than one monolayer (similar to 20 Angstrom thick). De-wetting was found to take place in a layered fashion for Zdol-TX and Z-Tetraol, with weakly bound second layers accreting into droplets, however, no layering was seen for Zdol during de-wetting, only droplets. The droplets eventually grew to the point where they could be observed by optical microscopy. In all cases, the first monolayer remained bound to the surface. Although the atomic force microscopy (AFM) tip could easily penetrate this first layer, it did not remove it.