This in silico survey shows that changes in the (anti)aromatic character of pi-conjugated heterocycles can be used to fine-tune their hydrogen (H-)bond strengths. Upon H- bonding dimerization, the pi-electrons of these rings can be polarized to reinforce or disrupt their (anti)aromatic re conjugated circuits (pi CCs)and stabilize or destabilize the resulting H-bonded complexes. H-bonding interactions that enhance aromaticity or relieve antiaromaticity are fortified, whereas those that intensify antiaromaticity or disrupt aromaticity are weakened, relative to analogues lacking full pi-circuits. Computed dissected nucleus-independent chemical shifts, NICS(1)(zz), reveal a uniform pattern and document changes in the magnetic (anti)aromatic character of the heterocycles considered. Recognition of this (anti)aromaticity-modulated H-bonding (AMHB) phenomenon offers insights into a range of fields from organocatalysis and self-assembly to pharmaceutical chemistry and molecular biology.