The Quranic discourse on Christians is paradoxical because its narratives express both compliments and condemnation, reproach and rapprochement. Scholars debate the sentiments behind the Quranic assertion that Christians are “certainly nearest in friendship” to the Muslim believers (Q 5:82). While some believe that this forms an incentive for rapprochement between Muslims and Christians, others interpret it in completely the opposite way. As such, this study aims to answer the fundamental question of whether Christian-Muslim friendship is possible. To come to a conclusion, it will examine the pros and cons of Christian-Muslim friendship that are detailed in both classical and modern exegeses concerning the nature of such friendship, the reasons behind it, and the identity of the friendly Christians mentioned in the Quran. It is expected that the result of this study will contribute to revising current understanding of Christian-Muslim relations.