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Antennary oligoglycines are synthetic products, obtained as a result of preliminary molecular design. Equal‐length antennae are built of glycine residues joined through the C end to an oligoamine branching core with an amine group at the N terminus exposed outside. The results of systematic research on the properties of aqueous solutions containing two‐antennary oligoglycine with four glycine portions are reported. The central feature is the competition between amphiphilic self‐assembly and formation of polyglycine II motifs. A combined procedure is developed to characterize bulk and interfacial structures and coatings. It includes registration of bulk aggregates, examination of interfacial layers at solution/air and solution/solid boundaries, drainage, and stability of liquid films. The obtained results provide new insight into the structure–property relationships in these smart fluids and give essential hints about key factors allied to possible applications in medicine, pharmaceuticals, and environmental protection. Oligo lightly: Equal‐length antennae are built of glycine residues joined through the C end to an oligoamine branching core with an amine group at the N terminus exposed outside. The properties of aqueous solutions containing two‐antennary oligoglycine with four glycine moieties are reported. The central feature is the competition between amphiphilic self‐assembly and the formation of polyglycine II motifs. [ABSTRACT FROM AUTHOR]