Friendship was a recurring motif in the literature of the Medieval period. This introductory chapter makes the argument that exploring the topic of friendship within the context of the literature of the turbulent Middle or Dark Ages is of contemporary relevance as we are faced in the twenty-first century with increasing global uncertainty. Friendship is seen as a concept that can bring people together peaceably. Just as we are still learning from the writings of Classical Greek and Roman philosophers, so were Medieval writers developing their ideas by interacting with the ancient works. A brief introduction to the writings of Antiquity that were influential on Medieval writers from Christian, Islamic and Jewish religious traditions and secular literature is provided, followed by some discussion of the importance of the role of friendship in the period before the Renaissance.