Aldehyde condensation is a reaction step in the oxidization of a lubricant base stock into high-molecular-weight products, forming sludge and a paint film, which lead to the failure of lubricating oil. Calculations on the basis of the density functional theory (DFT) were employed to investigate the reaction mechanism of the acid-catalyzed aldol condensation of a lubricant base stock. Carbonyl compounds could be converted into their resonant enol structures. However, the activation energy of the process was relatively high, and it was difficult to initiate. The existence of the acid could obviously decrease the activation energy of the reaction from 269.17–287.82 kJ/mol to 177.10–177.63 kJ/mol, and it significantly reduced the difficulty of initiating this reaction. The carbocation formed by the carbonyl compounds and acid could further react with the enol and produce an intermediate reaction product in which the chain of molecules grew longer. This process was not difficult to initiate, with a reaction activation energy of 65.10 kJ/mol. The intermediate product with a larger molecular weight could be converted into carbonyl compounds containing a β-hydroxy by removing a hydrogen proton from it. The energy barrier for this process was 193.15 kJ/mol, and it was not easy to initiate the reaction.