Love letters have been a means to bring distant lovers together for thousands of years, but their form has evolved along the changing modes of communication. Like other practices of love, love letters are not a given; but are entangled in the historical context in which they unfold, including the prevailing media at a given time. As John Storey and Katy McDonald observe in Media Love: Intimacy in Mediatized Worlds, “the use of media is not a supplement to contemporary practices of romantic love; it is increasingly fundamental and foundational to the construction and maintenance of such relationships” (2014, 221–222). In this chapter, I address the rhetoric of modern love correspondence—its various purposes, modes of communication, and meta-reflections on writing and media—from the beginning of the 20th century until today. I analyze how love and the beloved are mediated in the articulated desire and longing of love letters, and how love letters are used as a medium to overcome absence. I also reflect on the material status of love letters in relation to the technological development and the subsequent replacement of traditional letters by their digital counterparts, such as email, text messages, and real-time video chat like Skype.