The ability to control supramolecular and macroscopic self-assembly and disassembly holds great potential for responsive, reversible adhesives that can efficiently broker stresses accumulated between two surfaces. Here, cucurbit[8]uril is used to directly adhere two functionalized mica substrates creating surface-surface interactions that are held together through photoreversible CB[8] heteroternary complexes. Comparison of single-molecule, bulk, and macroscopic adhesion behavior give insight into cooperativity and stress dissipation in dynamic adhesive systems.