This dissertation examines letters as a site for the maintenance of long-distance friendship through four case studies of letter-writers spanning both poetry and prose as well as classical Latin through late antiquity: Cicero, Ovid, Fronto, and Paulinus. My first chapter argues that in letters, geographical distance can function as a cipher for other forms of distance and difference, allowing correspondents to both paper over and deemphasize inequalities of age, status, wealth, religion, commitment to the friendship, and more. Ausonius and Paulinus, for example, use the physical space between Paulinus’s family estates in Spain and Ausonius’s home in Bordeaux to talk around power differentials (Ausonius is forty years older and taught Paulinus when he was a young boy) and, perhaps most significantly, the growing chasm between their religious beliefs as Paulinus becomes more devoutly Christian. My second chapter observes that while intimacy in letters is often expressed through anticipation of physical reunion, in many cases the letter is more a site of nostalgia than of anticipation. Long-distance friends may or may not look forward to an upcoming reunion, but they frequently mythologize and look back on an idealized version of their past in-person friendship. The letter, I argue, allows fantasy to substitute for actual co-presence. Finally, my third chapter examines how the asynchronicity of letters shapes the kinds of intimacy they can foster. Ovid laments that it can take a full year for him to receive a letter in Tomis from Rome, so when he learns that Gallio’s wife has died, the asynchronicity of the letter fundamentally changes the kind of friend he can be. Such a belated consolation, he frets, could simply resurface old wounds—or Gallio could have remarried, dooming Ovid to offend the new couple by sending condolences instead of congratulations. Even in cases where the gap between written and lived time is only a matter of weeks or days, this untimeliness can create a sense of freedom that leads to greater candor, but it can also allow correspondents to avoid or ignore one another more effectively than they could in person. Once again, then, the letter becomes a way of talking about and around other forms of distance; temporal distance can exacerbate other gaps that exist between correspondents.