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A recurring challenge in extracting energy from ambient motion is that devices must maintain high harvesting efficiency and a positive user experience when the interface is undergoing dynamic compression. We show that small amphiphiles can be used to tune friction, haptics, and triboelectric properties by assembling into specific conformations on the surfaces of materials. Molecules that form multiple slip planes under pressure, especially through π-π stacking, produce 80 to 90% lower friction than those that form disordered mesostructures. We propose a scaling framework for their friction reduction properties that accounts for adhesion and contact mechanics. Amphiphile-coated surfaces tend to resist wear and generate distinct tactile perception, with humans preferring more slippery materials. Separately, triboelectric output is enhanced through the use of amphiphiles with high electron affinity. Because device adoption is tied to both friction reduction and electron-withdrawing potential, molecules that self-organize into slippery planes under pressure represent a facile way to advance the development of haptic power harvesters at scale.