Steady-state and time-resolved spectroscopic studies demonstrate that two members of the coumarin class of dyes, coumarin 7 (C7) and coumarin 30 (C30), undergo self-aggregation in water. The development of hypsochromically shifted new absorption bands in addition to the existing monomer bands with an increase in concentration of the dyes in an aqueous medium suggests that the aggregates are of H-type. An absorption-based kinetic study reveals that the rate of aggregation of C30 is an order of magnitude faster than that of C7. Second-order rate kinetics, as obtained from the half-life (t1/2) data, implies that the aggregates are dimeric in nature. Observations of isosbestic points in area-normalized absorption spectra (ANAS) and isoemissive points in area-normalized fluorescence excitation spectra (ANFES) and time-resolved area-normalized emission spectra (TRANES) establish that ground-state monomer ⇌ dimer equilibria for both of the systems are preserved in the photoexcited state. The present study further establishes that β-cyclodextrin is the most efficient of the three common cyclodextrins in shifting the equilibria toward the monomer by encapsulating the monomers within its cavity, making β-CD a convenient modulator to control the self-aggregation process. Dynamic light scattering (DLS), quantum chemical calculations, and molecular docking studies provide further support to our propositions.