The Cloud of Unknowing is an anonymous work written in the second half of the fourteenth century in north-east England. It is an epistolary-form guide to contemplative prayer, which is deeply connected to contemplative life as its formal framework. Through its four chapters, this paper analyses the communitarian dimension of contemplative life and examines its particularities. The first chapter provides an overview of previous research. Not only is there a lack of previous research on this topic, but the scope of issues covered by the studies that do exist is very limited. In addition, the issue of communitarian dimension of contemplative life has been completely bypassed. In the second chapter, after discarding the concept of “mystical problem” as a relevant approach to the issue dealt with in this paper (which either directly or indirectly represents the focus of scientific literature on the work The Cloud of Unknowing), we define the terminology and methodology used to address the issue of the communitarian dimension of contemplative life. Contemplative life is also differentiated from solitary life, a form of life that is narrower and more limited. Furthermore, we then consider the place that contemplative life occupies within the context of the Christian call, its formation as well as two methods – the cloud of forgetting and the cloud of unknowing – which, according to the anonymous author, endow the contemplative life with its distinct and specific features. In the third chapter, we analyse the communitarian dimension of contemplative life with respect to God, who represents the very source of contemplative life and who is also a communion within Himself. Participation of a person practicing contemplative prayer in the divine union is interpreted through theological virtues; in addition, it is argued that even the divine darkness of unknowing represents a form of union between that person and God. The fourth chapter analyses the communitarian dimension of contemplative life with respect to interpersonal relationships. These relationships can take three forms. The first form is ecclesiastical communitarianism, which implies that the person living a contemplative life is inseparably connected to the Church: professes its faith, participates in the liturgy, eases the hardships of the Church Suffering and multiplies the joy of the Church Triumphant. The second form is the institution of spiritual direction, which is a simultaneous expression of ecclesiastical and individual, i.e. personal communitarianism. The third form is social communitarianism. Charity is the fruit of contemplative love: a person practicing contemplative prayer is focused on the wider community to which he or she belongs. The community satisfies his or her existential needs, whereas the person practicing contemplative prayer through their spiritual experience and, if necessary, through concrete expressions of divine mercy, demonstrates the sublime nature of contemplation – naked desire for God Himself, detached from all things created. It is thorough this kind of prayer that he or she unites with God in spirit, love and will, loving all people with the same love that God has for everyone, which in turn makes contemplative life a supreme form of self-giving communitarian form of life.