This work considers the nature of the intermolecular hydrogen bond in a series of 15 different complexes with OH donor groups and N, O, P, or S acceptor atoms. To complement the existing literature, room-temperature gas-phase vibrational spectra of the methanol-pyridine, ethanol-pyridine, and 2,2,2-trifluoroethanol-pyridine complexes were recorded. These complexes were chosen, as they exhibit hydrogen bonds of intermediate strength as compared to previous investigations that involved strong or weak hydrogen bonds. Non Covalent Interactions (NCI) theory was used to calculate various properties of the intermolecular hydrogen bonds, which were compared to the experimental OH-stretching vibrational red shifts. We find that the experimental OH-stretching red shifts correlate strongly with the kinetic energy density integrated within the reduced density gradient volume that describes a hydrogen bond [G(s0.5)]. Given that vibrational red shifts are commonly used as a metric of the strength of a hydrogen bond, this suggests that G(so.5) could be used as a predictor of hydrogen bonding strength.