In this article Natalia Yakubova explores the interactions between theatre and literature as between an actress on one side and a man of letters on the other. The interactions discussed here came at a particular historical moment, when the transition from an actor-centred to a director-centred hierarchy was taking place, and the article deals with the letters written by actresses to the men who were playwrights and/or theoreticians of the new theatre: Eleonora Duse writing to Gabriele D’Annunzio, Vera Komissarzhevskaya to Valery Bryusov, Irena Solska to Jerzy Żuławski, and Gertrud Eysoldt to Hugo von Hofmannsthal. In each case study, attention is paid to the characteristics of the relationships between a given actress and a particular writer, their attitudes towards theatre reform, the way in which the actresses evaluated the literary status of their letter writing, and, significantly, the stylistic features of their writing. Natalia Yakubova is a senior researcher of the State Institute of Art Studies in Moscow, and was Marie Curie Fellow at the Institute of Literary Studies of the Polish Academy of Sciences between 2013 and 2015. She is author of O Witkacym (2010) and Teatr epokhi peremen v Polshe, Vengrii i Rossii 1990-ye–2010-ye (2014), and has published numerous articles in Russia, Poland, the USA, and Canada, among other countries.