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This paper investigates views on the possibility of friendship with the powerful in Roman imperial society, in particular in the works of the Stoic philosophers Seneca the Younger and Epictetus, and contrasts their perspective with those of Pliny the Younger in his Panegyricusand Plutarch in his political essays. Both Seneca and Epictetus caution their philosophically minded students to avoid the company of the politically powerful, lest they be corrupted by their ambitions and desires. Seneca the Younger entertains the possibility of teaching the emperor in his De clementia, but powerfully argues for example in his de brevitate vitaethat engagement with public affairs leads one away from his own self (7.3-8). Epictetus specifically addresses the discomfort that arises from being one of the emperor’s friends (Discourses 4.45-50).

Unlike in some of his philosophical works (e.g. De tranq. animi467D), Plutarch’s political essays advocate for philosophers to engage with rulers in the kind of teaching relationship usually reserved for philosophically minded friends or students, in order to spread the benefits of philosophical learning to the widest possible audience by shaping their leader’s perspective (Roskam 2002). From again a different perspective, Pliny’s Panegyricusclaims that Trajan restored the emotional content of friendship to the amici Caesaris(85).

These perspectives obviously partake in the rich variety of content and emotion that always shaped notions of friendship with the powerful in the Roman world (Williams 2012: 46-54). They can also be understood within the framework of the notions surrounding the ideal ruler, which evolve in this period, especially with regard to the Greek reception of Alexander the Great (Zecchini 2002). I argue, nevertheless, that these imperial texts reveal a particular tension between the philosophical ideals of friendly relations between teacher and student, and the political ideal of educating those in power in order to shape and enhance their rule. The philosophical ideal, at least in its imperial form, thrives on the critical aspects in friendly relations which are supposed to support the enhancement of the self and its truthfulness, but at the cost of psychologically cutting off relations with those in power. The political ideal might rely on a vocabulary of friendship and reciprocity in order to mask any potential sense of criticism, which imperial power cannot tolerate in a direct form, but it also allows for reasonably courageous interactions with the powerful (if not necessarily telling the truth to them). The paper concludes by situating this distinction in relation to previous scholarly thinking on parrhesiain the Roman empire, especially in the wake of the work of Michel Foucault (Foucault 2010); and I discuss how this splitting of truthfulness to oneself from the hopeful act of interacting with those in position of (autocratic) power complicates our understanding of imperial selfhood.