This chapter addresses 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. It analyzes 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. The chapter also reflects 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. Another common feature of love letters and emails are accounts of the couple's shared experiences. The materiality of a love letter written on paper is indexical. A technological platform such as Skype provides some options which go beyond the words and capabilities of letters: it opens a real time window to the world of the beloved.