We herein report the mixed micelle and monolayer formation of mixtures of a biocompatible and cleavable oxy-diester twin tailed (gemini) surfactant, 2,2′-[(oxybis(ethane-1,2-diyl))bis(oxy)]bis(N-hexadecyl-N,Ndimethyl-2-oxoethanaminium) dichloride (16-E1-16) with the triblock copolymer, P123 (HO(CH2CH2O)20(CH2CH(CH3)O)70(CH2CH2O)20H) using tensiometry, dynamic light scattering (DLS), and rheology. It was observed that P123 and 16-E1-16 have strong interaction and form small mixed micelles with similar micellar composition throughout the bulk mole fraction range with insignificant counterion binding. Besides, P123 and 16-E1-16 mixed surfactant system forms thermodynamically stable mixed monolayer that is rich in P123. Variation of viscosity with shear rate revealed better injectable property of the formulations of binary mixtures of P123 and 16-E1-16 compared to pure P123. Also, below α16-E1-16 = 0.3, all the mixtures were in the form of sol which transform into a weak gel at physiological temperatures making these formulations relevant as injectable delivery system. Solubilization capacity of these mixed micelles towards ibuprofen (IBU) showed that addition of 16-E1-16 to P123 micelles reduces its solubilization capacity but with the advantage of making the formulation injectable due to their favorable shear induced viscosity changes and thermogelation properties. Mixed micelles showed faster drug release rate predominantly following Fickian mechanism with negligible contribution of relaxation process in the release phenomena. There is no report showing interaction of biocompatible and cleavable gemini surfactant 16-E1-16 with P123 in mixed micelle and monolayer formation with detailed rheological, drug encapsulation and release studies even though this amphiphilic system has a potential to act as an injectable drug delivery system.