Bilayer graphenes are dimeric assemblies of single graphene layers bound together by π-complexation interactions. Controlling these assemblies can be complicated, as the layered compounds disperse in solvents or aggregate into higher columnar configurations and clusters. One way to assess the interactions that contribute to the stability of the layered compounds is to use molecular simulation. We perform pulling molecular dynamics on bilayer graphenes with different sizes and obtain the normal and shear force profiles of dissociation. We generate pathways of dissociation along the two directions and calculate the binding free energies of the structures with umbrella sampling simulations. We show that the dissociation process is direction-dependent. Along the shear direction, we compute the same free energy for the different samples, which validates the consistency of our simulations. We notice that the dissociation is less adiabatic on the normal than the shear direction, having an entropic contribution to the Gibbs energy. This contribution is more enhanced for the larger bilayer graphenes.