Liposomes based on hydrogenated phosphatidylcholine (PC) incorporating dihexadecyl phosphate (DHP) and 1-(4-(dihexadecylcarbamoyl) butyl)guanidinium p-toluene sulfonate (DBG), respectively, were mixed in aqueous dispersion at room temperature, and their molecular recognition effectiveness was investigated by turbidimetric measurements, microscopy, DSC, and isothermal titration calorimetry. Because of the high binding efficiency of the incorporated recognizable lipids, accurate results could be obtained for low DHP/PC and DBG/PC molar ratios (19:1), especially for enthalpy change measurements. The liposome-liposome interaction was further investigated as a function of the cholesterol content in mixed (PC-cholesterol) liposomes. At appropriate cholesterol concentrations, the organization of the recognizable moieties within the liquid-ordered phase of the bilayer membrane enhances molecular recognition at the liposomal interface.