Chalcogen⋯chalcogen interactions were investigated within four types of like⋯like and unlike YCY⋯YCY complexes (where Y = O, S, or Se). A plethora of quantum mechanical calculations, including molecular electrostatic potential (MEP), surface electrostatic potential extrema, point-of-charge (PoC), quantum theory of atoms in molecules (QTAIM), noncovalent interaction (NCI), and symmetry-adapted perturbation theory-based energy decomposition analysis (SAPT-EDA) calculations, were executed. The energetic findings revealed a preferential tendency of the studied chalcogen-bearing molecules to engage in type I, II, III, or IV chalcogen⋯chalcogen interactions. Notably, the selenium-bearing molecules exhibited the most potent ability to favorably participate in all the explored chalcogen⋯chalcogen interactions. Among like⋯like complexes, type IV interactions showed the most favorable negative binding energies, whereas type III interactions exhibited the weakest binding energies. Unexpectedly, oxygen-containing complexes within type IV interactions showed an alien pattern of binding energies that decreased along with an increase in the chalcogen atomic size level. QTAIM analysis provided a solo BCP, via chalcogen⋯chalcogen interactions, with no clues as to any secondary ones. SAPT-EDA outlined the domination of the explored interactions by the dispersion forces and indicated the pivotal shares of the electrostatic forces, except type III σ-hole⋯σ-hole and di-σ-hole interactions. These observations demonstrate in better detail all the types of chalcogen⋯chalcogen interactions, providing persuasive reasons for their more intensive use in versatile fields related to materials science and drug design.