Density functional theory calculations have been performed to quantify the aromaticity of 15,16-dimethyldihydropyrene relative to benzene through the dimethyldihydropyrene probe. Moreover, the strain energies in [e]-fused bis dihydropyrenes 6a–d are also calculated by comparison with a suitable reference system. The geometric analysis reveals that all isomers of the bis dihydropyrene 6 (6a–d) are strained, and the strain energies range from 5.87–11.31kcalmol −1 . The dihydropyrenes 6b and 6d show only splitting type distortion (S-) whereas 6a and 6c have additional arching type distortion (A-) which results in higher strain energies for 6a and 6c. A planar non-strained analog 7 has been proposed, and investigated to elucidate the aromaticity of dimethyldihydropyrene relative to benzene, through magnetic ( 1 H NMR and NICS) and geometric (bond fixation) criteria. The aromaticity of the dimethyldihydropyrene is estimated comparable to benzene. Moreover, magnetic and geometric parameters of 6a–d are also discussed within the context of their inability to estimate the aromaticity of dimethyldihydropyrene.