How could a fervent skeptic (as Cioran was in his youth) engage with a religious philosopher with systematic tendencies like Nae Ionescu? A detractor of philosophy with a philosophy devotee? Such are the questions we have to begin with when considering the challenging connection between the two. The conclusion will be that, despite the friendship between the two thinkers, they had rather different philosophical views. However, even though they stand at opposite ends from the perspective of these questions, we can find a fundamental common element in the two great Romanian thinkers, and they can also be joined philosophically, not only through the friendship relationship between a teacher and one of his favorite students: this common element would be an interest in religion, but from fundamentally opposite positions, one being a believer, the other a non-believer.