This chapter explores the potential and challenges of basing pedagogical, bilingual electronic dictionaries on WordNet – a comprehensive machine-readable lexical database of the English language. It introduces the specifics of WordNet’s complex lexical architecture; explores the interfaces between WordNet and humanistic, pedagogical and bilingual lexicography; and highlights the Transpoetika Dictionary – an innovative, bilingualised Serbian-English pedagogical dictionary. The chapter shows that the potential of relational lexical databases by far exceeds their exclusive application in language engineering and automatic text processing. The author argues that WordNet can not only serve as a general lexicographic framework for building humanistic eDictionaries, but also pave the way for other collaborative projects in Natural Language Processing (NLP) and pedagogic lexicography. The author also discusses strategies for expanding the scope of WordNet-based humanistic dictionaries through web services and social media platforms such as Flickr and Twitter.