Examining, for a symposium on xenophilia, the views of some of the period’s most open-minded and tolerant thinkers, as well as the historical development of Christian writers’ treatment of Muslims, this article considers whether the term Islamophilia can be applied to any Christian’s attitudes during the Middle Ages. The analysis considers what qualifies as an expression of love for Muslims, the distinction between positive regard for Islam and positive regard for Muslims, and whether Islamophilia essentializes Muslims in the same way that Islamophobia does. The author argues that any search for Christian Islamophilia must be broad enough to encompass evidence found in unexpected places. For instance, due to the Christian belief that Muslims who did not convert to Christianity would suffer eternally, a desire to convert them may well qualify as a stance of love toward them, despite the offense to modern sensibilities that such implies. Paradoxically, indifference toward Muslims’ religion, such as on the part of neighbors or business partners, might also have a place in a discussion of Islamophilia, precisely because it rejects essentialism.