Enantioselective wetting of a chiral polymer film was demonstrated. The contact angle of chiral liquids on the film was strongly dependent on their chirality although their physical properties including surface tension were identical. Such wetting behavior resulted from the enantioselective surface reorganization involving local conformational change of the polymer chains at the liquid interface. The concept of "dynamic interface for chiral discrimination" has possible potential for the development of materials capable of chiral sensing, optical resolution, and asymmetric synthesis.