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This article offers philosophical background to Seneca’s letters on friendship and Cicero’s dialogue Laelius de amicitia, with a particular focus on Stoic theory. Recent scholarship has revised the view that Stoic friendship is impersonal or that friends are interchangeable; instead, Stoics can love friends for their own sake, and even as moral goods. In an attempt to clarify why only the wise can be friends, according to the Stoics, the article highlights two core values of Stoic friendship: reliability and mutual assistance. Reliability is grounded in the wise person’s inner coherence: only the sage has stable, non-conflicting beliefs, making genuine trust and steadfastness possible. Stoic reflection on the need for mutual assistance has a Platonic-Aristotelian pedigree in the question whether friendship arises from need or human nature. Seneca grapples with this problem in a few of his letters: while the wise are self-sufficient for happiness, they not only need other people in order to live, but they also can make good use of the uniquely rational assistance given by their wise friends.