This paper seeks to understand He Xinyin’s reassessment of the notion of friendship and its subversive dimension in several of his major essays. This reassessment was part of an increase in discourses on friendship in China in the 16th-17th centuries, which was in some ways prompted by the decay of traditional structures, particularly the family structure, that served as the basis for the social functioning of the empire. He Xinyin was one of the most innovative and radical thinkers whose redefinition allowed friendship to take, for the first time, a foremost place among the five social relations, to be conceived as a subjective relationship where the individual emerges as a primary entity, and to form the ground of two major freedoms, the freedom of expression and the freedom of association.