Flexibility and chirality of molecules are two cornerstones of modern chemistry, underlying vast array of biochemical and biological processes that take place in living organisms. The former concept and its role in this respect has been investigated and documented for over 70 years, including its critical role in the interactions occuring between enzymes and their substrates and, more generally, between receptors and ligands. Flexibility thus represents one of the mainstays of a generalized catalytic mechanism. While the concept of chirality has been introduced more than a century ago, certain manifestations of this phenomenon have been properly investigated for a relatively short period of time and, despite recent experimental and theoretical efforts, the complete understanding of this phenomenon is yet to be accomplished. Interestingly, although it is precisely the interplay between the two that plays a crucial role in the fields of biochemistry and molecular medicine/pharmacology, e.g. being necessary for the development of conceptually novel systems for targeted drug delivery, it is also significantly more scarcely investigated and understood than either of the two underlying concepts.