Cocrystallizing a given molecule with another can be useful for adjusting the physical properties of molecules in the solid state. However, most combinations of molecules do not readily cocrystallize but form either one-component crystals or amorphous solids. Computational methods of crystal structure prediction can, in principle, identify the thermodynamically stable cocrystal and thus predict if molecules will cocrystallize or not. However, the pronounced polymorphism and tendency of many organic molecules to form disordered solids suggest that kinetic factors can play an important role in cocrystallization. The question remains: if a binary system of molecules has a thermodynamically stable cocrystal, will it indeed cocrystallize? To address this question, we simulate the crystallization of more than 2600 distinct pairs of chiral model molecules of similar size in 2D and calculate accurate crystal energy landscapes for all of them. Our analysis shows that thermodynamic criteria alone are unreliable in the prediction of cocrystallization. While the vast majority of cocrystals that form in our simulations are thermodynamically favorable, most coformer systems that have a thermodynamically stable cocrystal do not cocrystallize. We furthermore show that cocrystallization rates increase 3-fold when coformers are used that do not form well-ordered single-component crystals. Our results suggest that kinetic factors of cocrystallization are decisive in many cases.