UV-Vis absorption spectra and emission peaks of indole and 7-fluoroindole are measured and it is observed that 7-fluoroindole quenches the fluorescence signals significantly compared to indole. This observation is elucidated via reconstruction of the potential energy surfaces, determination of the conical intersections, and dynamical studies. It is observed that a single fluorine substitution on indole leads to the appearance of several accessible low-energy conical intersections that cause fast nonradiative decay. In this paper, we have investigated the nonradiative processes of Ind and 7F-Ind theoretically using high-level methods, such as EOM-EE-CCSD, SA-CASSCF, MS-CASPT2/6-311++G(d,p) levels of theory, to study these pathways and their feasibility.