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The nature and strength of the interactions between the 1,3-bis(dimethylhexadecyl)propanediammonium dibromide (16-3-16) gemini surfactant and a homologous series of nonionic polyoxyethylene (20) sorbitan ester surfactants having laurate (Tween 20), stearate (Tween 60), or oleate (Tween 80) alkyl tails has been investigated. The critical micelle concentration (cmc) values of the mixed gemini–tween systems were determined using the du Noüy ring surface tension method, and the results have been analyzed using Clint’s, Rubingh’s, Motomura’s, and Maeda’s theories for mixed micellar systems. The results demonstrate a synergistic mixing behaviour between the Tween surfactants and the 16-3-16 gemini surfactant, where the strength of interaction is dependent upon the chain length and saturation of the Tween alkyl tail.