This paper adds ammunition to recent arguments for the possibility of online character friendships in the Aristotelian sense. It does so by exploring sustained and deep email correspondence or epalship as a potential venue for the creation, development and maintenance of character friendships, and by drawing an analogy with a historically famous example of penpalship: that forged between Voltaire and Catherine the Great. It is argued that epalships allow for various technological extensions in the cyberworld of today that were not available to Voltaire and Catherine; and that augmented with those extensions, there is even more reason for seeing epalships as potentially making the grade as true character friendships than traditional penpalships. However, despite being potentially categorisable as character friendships, mature epalships are vulnerable to the same problems and pitfalls as other examples of character friendships, and perhaps even more so: pitfalls that were mostly overlooked by Aristotle himself.