Halogen bonding (XB) is often described as an intermolecular attraction between an electron rich species and a covalently bonded halogen atom that has an area of positive potential, as known as a σ-hole. This model suggests that there is a connection between the strength of the XB and σ-hole on the surface, whose size can vary greatly depending on the molecule. Theoretical studies have shown that polarization plays an important role, but there has been little experimental data to back this up. In this project, we examined competing halogen and hydrogen bonding (HB) and established the effects that polarization plays on both the hydrogen and halogen bonding for a number of halogenated compounds by comparing formation constants for the XB and HB complexes with the values of maximum electrostatic potential on the surface of the halogen and hydrogen atoms, VmaxX and VmaxH, respectively, for both the isolated and polarized molecules. The halogenated compounds (XB donors) used were iodoform, bromoacetonitrile, bromonitromethane, and diiodomethane. As the XB acceptors, iodide, bromide, and chloride anions (taken as salts with tetrapropylammonium or tetrabutylammonium counter-ions), as well as 1,4-diazabicyclo[2.2.2]octane (DABCO) were used. Competing HB and XB characteristics in solutions were characterized using a combination of 1HNMR and UV-Vis measurements because XB causes an upfield shift in 1HNMR spectra and a new absorption bands in UV-Vis spectra while HB causes a downfield shift and no new absorption bands. This in conjunction with computational data helped determine the formation constant and ε values for the systems studied. It also showed that there is a correlation between the Vmax of a polarized molecules and their binding energy that is not in the Vmax of the individual molecule.