The electronic structures of tetrachalcogen tetranitrides, E4N4, and octachalcogen dications, E-8(2+), and the nature of their intramolecular E center dot center dot center dot E interactions (E = S, Se) was studied with high-level theoretical methods. The results reveal that the singlet ground states of both systems have a surprisingly large correlation contribution which functions to weaken and therefore lengthen the cross-ring E-E bond. The observed correlation effects are primarily static in E4N4, whereas in E-8(2+) the dynamic part largely governs the total correlation contribution. The presented description of bonding is the first that gives an all-inclusive picture of the origin of cross-ring interactions in E4N4 and E-8(2+); not only does it succeed in reproducing all experimental structures but it also offers a solid explanation for the sporadic performance of different Computational methods that has been reported in previous studies. Furthermore, the theoretical data demonstrate that E center dot center dot center dot E bonds in E4N4 and E-8(2+) are unique and fundamentally different from, for example, dispersion that plays a major role in weak intermolecular chalcogen ... chalcogen contacts.