It ought to be an ongoing effort by all scholars/researchers to question the validity, legitimacy, and purposes of their own discipline because we live in an ever-changing world and must regularly reflect upon our academic self-justification. This also applies to the field of Medieval Studies that faces considerable difficulties and challenges today with declining numbers of students enrolling in respective classes and lacking support by university administrators. This study begins with a general consideration on where we are today in terms of justifying the humanities at large, that is, of the study of literature particularly, and hence of medieval literature. Then this paper focuses on two universal themes, tolerance and then love. While love has always been associated with the courtly world since the twelfth century, toleration and even tolerance do not seem to fit within the medieval context. However, the discussion of both phenomena can be utilized as a particularly effective catalyst for further investigations of medieval culture and literature within the framework of modern and postmodern responses to the Middle Ages. The exploration of this theme as it emerged already at that time offers intriguing opportunities to make the study of medieval literature relevant and important for us today, as does the examination of the love discourse through a historical lens.