A commonly accepted interpretation of how Christians and Muslims perceived and responded to each other during the medieval period remains elusive. While broad surveys have established the existence of dominant perspectives and trends, smaller-scale studies are revealing that responses could be much more complex and nuanced. This article attempts to negotiate a middle ground to examine the perceptions of Islam and Muslims of three mendicant friars. The study demonstrates that direct encounters with Muslims, and their customs, practices, and beliefs, or active engagement with Greco-Arabic philosophy, or both, provided these three men with new means to rationalise the reality of Islam and its followers, breaking the bonds of traditional ideological responses and enabling them to produce novel and more informed perspectives on both. It indicates the potential impact that inter-cultural engagement may have had on the inter-religious perceptions of mendicant friars in the latter part of the thirteenth century.