The collective mind often attributes the image of a modern Latin classroom to a teacher writing on a chalkboard in front of students eagerly memorising the declensions in silence. However, as part of their search for innovative and effective practices, Latin instructors have consistently expanded their gaze beyond the traditional parameters of rote memorisation for at least since the pioneering efforts of W.H.D. Rouse, looking to more innovative models presented by novel methods for inspiration and to the halls of predecessors in hopes of fostering a more engaging learning environment. Upon close comparative study between the modern pedagogical methods in Latin classrooms and the perspective of Renaissance scholar Petrarch, this study identified a commonality between the two: emphasis on dialogue between different members of the classroom and personal interpretations of preceding authors’ works for a better opportunity of comprehending the content. Grounded in the philosophies of the Socratic method, Petrarch claimed that an important element of the tradition of pedagogy finds expression in dialogues, imitation, and the significance of fully comprehending the topic in pursuit of wisdom. Likewise, many institutions of the U.K. and the United States, strengthened by the emergence of dialectic assessment applications during the Covid-19 Pandemic, are working towards a new norm in place. After conducting an in-depth interpretation of primary and secondary sources regarding Petrarch's pedagogy, as well as research of its modern developments and the applications, the comparison suggests a new direction for the Classics community to consider going forward.