In this manuscript we analyze the Cambridge Structural Database (CSD) to compare the relative importance of halogen, chalcogen and pnicogen bonding. The three interactions can be explained in terms of electrostatic effects, considering the halogen, chalcogen or pnicogen as a Lewis acid due to the presence of a sigma hole (σ-hole). We have studied the behaviour of the three interactions considering two types of Lewis bases: amines and arenes. Combining the CSD search and a comprehensive theoretical study (DFT-D3) we conclude that the halogen bonding interaction is the energetically most favourable when the electron donor is an amine. In contrast, the pnicogen bond is the most favourable if the Lewis base is benzene (pnicogen–π interaction).