In this study, the vapor phase lubrication of interacting gold surfaces has been investigated on the atomic and molecular level using the quartz crystal microbalance (QCM), atomic force microscopy (AFM) and scanning tunneling microscopy (STM). These techniques have provided a fundamental understanding of the molecular nature of adsorption, adhesion, and current flow occurring at gold interfaces through the formation of self-assembled monolayers (SAMs) of conjugated aromatic thiol molecules. The issues of static adhesion and contact performance have been addressed simultaneously in relation to the nature and composition of the interface. Maps of both current and adhesion demonstrated the potential of using conjugated species with fluorine substituents on the basis of their tribological and electrical behavior as candidates for lubricating Au/Au interfaces in MEMS devices. Although they do not form a closely-packed geometry compared to n-alkanethiol SAMs, they however provide hydrophobic, Teflon-like surfaces which accounts for the observed low adhesion.