The search is on for stable isolated borylenes. Potential roles in modern synthetic chemistry for boron analogues of carbenes continue to motivate interest in locating them. Using density functional and ab initio methods, we posit and examine the thermochemistry, and chemical bonding, including aromaticity, of several classes of 5- and 6-membered borylenic rings. In these systems, cyclization relies on dative bonding (ouroboric coordination) and π donation to a monovalent boron center from an adjacent O center. Certain neutral five-membered rings (heterocyclic cyclopentadienyl analogues) in particular are found to exhibit exceptionally strong preferences for the singlet multiplicity, each with singlet–triplet (S–T) gaps in excess of 40 kcal·mol–1. The singlet five-membered rings with the largest S–T gaps and some of the six-membered rings show evidence of weak aromaticity. Relationships of the form N = A·r –b , in line with Gordy’s and other functions linking bond order, N, and covalent bond length, are identified for dative B←O contacts, r, reinforced in rings by π-delocalization.