In this paper we present our experience in building a visual file manager, VennFS2, that offers to users an adaptive interface toward access to files. Our file manager was originally designed to overcome some of limitations of hierarchical file systems, since it allows users to categorize files in such a way that files may belong multiple categories at once. Based on the past history of the files that were opened and modified by the user, VennFS2 graphically presents the user a small number of choices of the next file the user will modify. Some preliminary testing with interesting hints are also reported. Categories and Subject Descriptors H.5.2 [User Interfaces]: Interaction styles General Terms Venn diagram Keywords Set, Venn, User Interfaces, Adaptivity