Even as friendship carries overwhelmingly positive connotations, the categories of “fair-weather friend” or “frenemy” indicate that less-than-ideal friendship is commonplace. What remains poorly understood is how people make sense of the persistence of their imperfect friendships. Drawing on studies of difficult friendships and friends who cohabitate, this chapter offers an interpretive perspective on how and why friendships that people characterize as difficult persist. Using the concept of the “good enough friend,” we unsettle ubiquitous yet simplistic directives of modern therapeutic culture to “cut off” difficult relationships. We argue that the potential for ease and difficulty are equally inherent to what friendship is, and that by attending to “difficult” ones and how people evaluate their worth, we can better understand how people navigate concord and conflict in personal life. We advance the intervention that a critical friendship must resist hierarchies of intimacy inherited from Western philosophical traditions that rank easy, pleasurable friendships as inherently “better” than ambivalent ones, which may also have core places in people’s lives.