Two-dimensional proton nuclear magnetic resonance (2D 1H NMR) relaxometry is increasingly used in the field of wood sciences due to its great potential in detecting and quantifying water states at the level of wood constituents. More precisely, in this study, this technique is used to investigate the changes induced by “natural” and “artificial” aging methods on modern and historical oak woods. Two bound water components are detected and present differences in terms of association to the different wood polymers in cell walls: one is more strongly associated with wood polymers than the other. The evolution of the two bound water types is discussed in regard to aging methods and is related to the structure of the cell wall, especially with the S2 layer and the evolution of wood chemical composition (cellulose, hemicelluloses and lignin). The evolution of hydric strains is also discussed taking into account the effect of aging methods on the two bound water components. The obtained results confirm the ability of 2D 1H NMR relaxometry to evaluate the effect of aging at the molecular level and on hydric deformation. Furthermore, this method shows that it is possible to determine the moisture content of wood without the necessity to oven-dry the wood material.