The association of the like and unlike configured propeller and butterfly conformers of unionized and bay-ionized 7,14-, 1,6-, and 1,7-tautomers of hypericin was investigated by means of semiempirical calculations of the MM3 type. From the various possible stack dimers it was found that the homodimer with like configurations of the propeller conformations of unionized hypericin was the most stable one, making them strongly stabilized over any coplanar arrangements. Oligomerization led to further stabilization of the stacked homoassociates up to five units. Adding more units did not lead to further stabilization. Accordingly, dispersion forces between the aromatic systems dominate in associate stabilization, with hydrogen bonding playing a marginal role only. These findings were compared with the rather scarce experimental evidence.