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An aza‐BODIPY dye 1 bearing two hydrophobic fan‐shaped tridodecyloxybenzamide pendants through 1,2,3‐triazole linkages was synthesized by a click reaction and characterized. 1H?NMR studies indicated that dye 1 exhibited variable conformations through intramolecular H‐bonding interaction, which is beneficial for the polymorphism of aggregation. The thermodynamic, structural, and kinetic aspect of the supramolecular polymerization of dye 1 was investigated by UV/Vis absorption spectroscopy, IR spectroscopy, AFM, TEM, and SEM. Biphasic aggregation pathways of dye 1 , leads to the formation of off‐pathway, metastable Agg.?I and thermodynamically stable Agg.?II with distinct H‐aggregation spectra and nanoscale morphology. The living manner of the supramolecular polymerization of dye 1 was demonstrated in seeded polymerization experiments with temperature‐modulated successive cooling–heating cycles.