The importance of cholesterol in the molecular structure and organization of cell membranes is a topic of great research interest. It has been hypothesized that the lateral heterogeneity of cell membranes arises from the dynamic self-assembly of cholesterol enriched nanodomains. In order to elucidate the fundamental molecular interactions involved in the assembly of these nanodomains, binary lipid monolayers of dimyristoylphosphatidylethanolamine (DMPE) and dihydrocholesterol (DChol) were studied as model systems and probed using grazing incidence x-ray diffraction (GIXD). Mixed DMPE/DChol systems were shown to exhibit short-ranged lateral ordering consistent with previous data for a lipidic alloy of egg sphingomyelin and DChol that obeys Vegard's law [Phys. Rev. Lett 2009, 103, 028103]. In the presence of β-cyclodextrin (CD), DChol was selectively removed from the membrane. GIXD was used to monitor the changes of lipid ordering during CD mediated desorption of DChol to the subphase. The chemical of amount of CD to DChol was greater than a factor of 1000 and complete DChol depletion was expected. However, it was observed that a significant amount of DChol remains in the membrane during the experimental time frame of a couple of hours and this resistance to CD transfer could be due to the stability of condensed complexes formed between DMPE and DChol.