We have studied the linear optical response and orientational relaxation dynamics of a family of rhodamine dyes in which there is substantial variation in the chromophore structure. For these chromophores, the identity of a substituent at the center ring (1) position mediates the linear optical response of the chromophore, and semiempirical calculations provide agreement with experimental data. This phenomenon can be understood in terms of the extent of conjugation of the chromophore ring system. The reorientation data for these chromophores in several polar protic and aprotic solvents are nominally consistent with the predictions of the modified Debye-Stokes-Einstein (DSE) model. In several cases, polar aprotic solvents are found to interact more strongly than polar aprotic solvents with the rhodamine chromophores, despite the difference in the nature of intermolecular. interactions in the two types of solvents. The terminal amino functionalities on the rhodamines exhibit stronger interactions with protic solvents than the analogous chromophores that have been structurally modified to constrain amino group rotation. The data point to the importance of both site-specific solvent-solute interactions and dipole-dipole interactions in mediating the solution phase dynamics of rhodamines.