This paper aims to explore Christopher Marlowe’s rendering of the irony of forbidden desire and his understanding of the Reformation and Renaissance humanism by examining The Tragedy of Doctor Faustus and Edward II. Faustus and Edward, alter egos of the playwright, lead a life full of transgression by building forbidden bonding either with a demonic agent or with a homoerotic friend, a kind of homosociality with pernicious companions. Ironically, however, their transgression raises questions about a fundamental meaning and nature of faith and friendship. As a sympathetic desire sharer with Mephistopheles, Faustus betrays his skepticism about the authenticity of the faith system of his times, developing a spiritual homosociality with the fallen angel, though their communion leads to the freethinker’s damnation. Edward’s homoerotic friendship with low-born Gaveston and the nobles’ repulsion toward them reflect the tension between a king’s two bodies, particularly underlining the impaired and languished authority of monachical sacrality in the period of transition from divinely-ordained kingship to Machiavellian realpolitik. Though failed as a monarch, however, Edward’s pursuit of friendship makes a sharp contrast with power-oriented and self-serving peers, all of which emphasizes the value of human relationship in the play.