In the classical theory, holomorphic quadratic differentials are tied to a wide range of objects, e.g. harmonic functions, minimal surfaces and Teichmüller space. We present a discretization of holomorphic quadratic differentials that preserves such a rich theory. We introduce discrete holomorphic quadratic differentials and discuss their connections to the surface theory and Teichmüller theory. On one hand, holomorphic quadratic differentials are related to discrete minimal surfaces via a Weierstrass representation. On the other hand, they arise from deformations of circle packings on surfaces with complex projective structures.