This chapter argues that the question of how one can “speak with oneself” (secum loqui) was central to Cicero’s personal, philosophical, and political projects throughout much of his career, and especially in his late works. Set against the background of scholarship on Cicero’s life and work, Petrarch’s interest in Cicero, and the wide arc of Cicero’s philosophical works, it studies Cicero’s dilations on the paradox of solitude—including Scipio’s adage, “Least alone when most alone”—in the years 46 to 43 BCE. It explores Cicero’s treatment of solitude in his letters (especially to Atticus) and in major works on either end of this period, works that rewrote social genres in solitary form: the Brutus and Orator, it shows, reimagined oratory in the deserted forum, while his Laelius de amicitia answered the question Aristotle had left hanging, and of great interest subsequently to Montaigne, whether persons can be friends to themselves.