The molecule l-H-pyrrolo[3,2-h]quinoline (1-HPQ) (alternatively pyrido[3,2-glindole) and its 1-methyl derivative (1-MPQ) are shown to exhibit a pronounced dipolar-relaxation red shift of their principal fluorescence in protic solvents. For 1-HPQ, the red shift is Delta v = 2232 cm(-1), comparing methanol with methylcyclohexane solutions (lambda(max) 363-395 nm for 1-HPQ, 298 K). For 1-HPQ a second, weaker long-wavelength fluorescence is observed at lambda(max) 565 nm in methanol at 298 K, a shift of 7617 cm(-1) from the fluorescence band maximum of the normal tautomer (at 395 nm); this is shown to be a proton-transfer tautomer fluorescence. The dual fluorescence of 1-HPQ in protic solvents is evidently the result of an unusual competition between the competing pathways of dipolar relaxation and excited state proton transfer. Two models are discussed for the excitation dynamics, leading to the conclusion that two populations of solvated 1-HPQ molecules exist in protic solvents, one promoting excited state double proton transfer catalyzed by a solvent bridge, and the other permitting primarily dipolar relaxation.