Long molecular ligands or "tethers" play an important role in the self-assembly of many nanoscale systems. These tethers, whose only interaction may be a hard-core repulsion, contribute significantly to the free energy of the system because of their large conformational entropy. Here, we investigate how simple approximate models can be developed and used to quickly determine the configurations into which tethers will self assemble in nanoscale systems. We derive criteria that determine when these models are expected to be accurate. Finally, we propose a generalized two-body approximation that can be used as a toy model for the self-assembly of tethers in systems of arbitrary geometry and apply this to the self-assembly of self-assembled monolayers on a planar surface. We compare our results to those in the literature obtained via atomistic and dissipative particle dynamics simulations.