We propose D-FLIP Paintings, a dynamic, flexible, and interactive display method of paintings aimed at education of art appreciation. This system dynamically makes a flexible layout of hundreds of paintings in real time according to the variety of interactions among the users. It is expected to provide proactive learning and new insights through dialogues among students for communicative art appreciation. To clarify the performance of a system using this method, we conduct a comparative experiment on practical teaching in the field by using our system and existing inflexible digital media. The results show that D-FLIP Paintings is useful for communicative art appreciation. In using D-FLIP Paintings, students proactively choose paintings of interest from a large body of paintings, and the dialogue among students during their group appreciation sessions is more active.