For alkyne-containing compounds, we devised an alternative method for determining sp -hybridization of atoms involved in an alkyne to ultimately reveal a conjugated pi system in the compound that agrees with our inclusive vs. non-inclusive steric number calculation. This approach involves the idea that the pi electrons of a pi bond within an alkyne that are not involved in the conjugated pi system (due to these p-orbitals being perpendicular relative to the parallel p-orbitals contributing to conjugation 4 ) can occupy a single atom in the alkyne, but the specific atom they occupy is unclear. Therefore, we present a "lone pair hybrid" that accounts for both atoms being equally able to receive the pi electrons as a lone pair. These hypothetical lone pairs are localized due to an alkene still bonding the atoms and makes the steric number calculation for both the inclusive and non-inclusive approach 2 sigma bonds + 1 lone pair = 3, sp , making the atoms sp 2 -hybridized and thus revealing the conjugated pi system. The lone pair hybrid model utilizes the inclusive vs. non-inclusive steric number calculation method to (1) confirm that the atoms involved in the alkyne in the original structure are now sp 2 -hybridized and (2) determine the most stable aromatic configuration of alkyne-containing compounds. This model is an alternative approach from performing homolytic cleavage to turn the carbon atoms involved in the alkyne into radicals, which are sp 2 -hybridized . While both approaches reveal conjugated pi systems, the lone pair hybrid model is able to be used in conjunction with our inclusive vs. non-inclusive steric number calculation method to further determine the aromaticity of the compound.