One of the most emblematic Middle Eastern love narratives in medieval period – Shaykh San??n’s love story – appears in Far?d al-D?n ?Att?r Nish?p?r?’s (1145/6-1221) Mantiq al-Tayr. Shaykh San??n is an eminent ascetic P?r who has never transgressed any of the Islamic traditions. However, when he travels to Rome after a dream, he sees a beautiful Christian girl and falls in love. He forgets Islam and its traditions, converts to Christianity and begins drinking wine, going to taverns, wearing zunn?r (belt worn by non-Muslims) and herding pigs. His conversion to Christianity was blasphemous and an absolute rebellion at the time. However, through this transgressive love, he undergoes a spiritual transformation, turning from an ascetic to a mystic. Similarly, one of the most impassioned love stories in medieval European literature is that of Peter Abelard (1079-1142) and his student, Heloise (1101-1164). The couple find themselves so attached to each other that neither can withstand the spiritual and physical desires while both know that the laws of the time forbid their relationship. Nonetheless, as in Shaykh San??n’s case, love is a power impossible to resist. Their passionate love scandalizes the community of the time; and although separated, their love endures through their letters. After nine hundred years, we can still find rigid policies resulting in theological and sexual repression in various societies. Shaykh San??n’s, and Abelard and Heloise’s love stories and their religious transgressions speak about medieval Middle Eastern and European societies’ understanding of religious tolerance, sexual equality, and power of love. From across the centuries, these stories inspire and ask us to reason and to question. I argue that the power of love allows these couples to be extraordinary; to transgress social, moral, ethical and sexual boundaries; and to realize that the reason for human existence is love. Tolerance and embrace of human diversity, and not the shoring-up of social, religious and sexual boundaries, is their way of loving divinity; their religion. From a historical point of view, their love stories are precious in showing that regardless of all the laws and prohibitions; inclusiveness (of transgressors) was thinkable in those days.