While therapy culture has long been a part of the repertoires through which people think about and practice their romantic relationships, it has been less prominent in how they envision friendship. However, based on our interviews on experiences of friendlessness in an Atlantic Canadian city, we show that therapeutic styles increasingly shape how people orient to friendship, even as friends rarely seek formal therapy to manage their conflicts. This article focuses on how modern therapy culture, with its emphasis on individual wellbeing, self-knowledge, and ‘healthy’ rather than ‘toxic’ relationships, presents people with conflicting cultural imperatives for how to practice their friendships. On the one hand, therapy culture encourages people to seek out friends to whom they can disclose their most intimate feelings and experiences – friends who will offer support, understanding, and validation. On the other hand, therapy culture equally cautions that one must maintain ‘boundaries’ to protect oneself from friends’ personal revelations or ‘traumas.’ We ask what these dual imperatives mean for modern friendship and how people experience the tension between them. We argue that one reason modern friendship can be difficult is that divulging one’s intimate feelings or experiences to a friend can be interpreted as either building intimacy or burdening others with one’s problems, or crucially, both at the same time. Our findings lead us to ask how therapy culture might increasingly turn friendship into a reflexive object or something else to ‘optimize’ rather than providing an escape from relationships that demand ‘work.’