The energetics of intramolecular hydrogen bonds (H-bonds) is a subject of fundamental importance in chemistry and biochemistry. In contrast with intermolecular H-bonds, whose enthalpy can be determined by experiment or accurately evaluated through a supermolecular approach, there is no general accepted procedure to determine the enthalpy of an intramolecular H-bond. In this work, different ways for assessing the energetics of intramolecular H-bonds of selected aromatic systems were applied and compared. They include the widely used conformational analysis approach (cis-trans method), a recently proposed isodesmic reaction method, and a new procedure that we designate as the ortho-para method. Energy calculations were carried out at several theory levels, including a modified complete basis set extrapolation method (CBS-QMPW1), in which the geometries are based on MPW1PW91/aug-cc-pVDZ density functional theory optimizations. The obtained results, together with a simple dipole-dipole interaction model, help to explain why the enthalpies of intramolecular H-bonds are often overestimated by the cis-trans method. The results also show that intramolecular H-bond enthalpies based on the isodesmic reaction method may be unreliable. The orthopara method, which can be applied when accurate theoretical or experimental standard enthalpies of formation are available, is probably the best way of estimating the enthalpies of intramolecular hydrogen bonds. Finally, our results illustrate the important role played by intramolecular H-bonds in the energetics of homolytic dissociation reactions involving di-substituted benzenes.