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We here present how rebalancing the interplay between H‐bonds and dispersive forces (Van der Waals/π–π stacking) may induce or not the generation of kinetic metastable states. In particular, we show that extending the aromatic content and favouring the interchain VdW interactions causes a delay into the cooperative supramolecular polymerization of a new family of toluene bis‐amide derivatives by trapping the metastable inactive state. [ABSTRACT FROM AUTHOR]