The article comments on an incomplete collection of German letters exchanged in the years 1925–1933 by the poet and Catholic priest Jakub Deml (1878–1961) and the philosopher, publicist and follower of Judaism Theodor Lessing (1872–1933). It introduces an edition of a few selected letters preserved in the Literary Archive of the Museum of Czech Literature in Prague. The author notes the critical events which both marked the correspondents’ friendship and determined the topics of their correspondence (German students’ attacks against Lessing in 1925 - the death of Otokar Březina in 1929 - the political persecution, exile and assassination of Lessing by the Nazis in 1933). She also focuses on the shared themes and motifs in their poems and prose. In addition, Deml turned Lessing into a character of his documentary books. Overall, he repeatedly defends Lessing as a dear friend and victim of contemporary ideology. However, in the period from 1930 to 1940 he also repeats statements made about Lessing by another mutual friend, Otokar Březina, in a way that chimes with the antisemitic prejudices of the time. The reader is then confronted by the fact that Deml’s characters do not agree with one another either in word or in thought but in practice they act mostly independently of their ideas and follow basic sympathies or imperatives, such as the duty to help one’s neighbour in need. In the end, in Deml’s writing Lessing played not only the double role of a beloved friend and a rejected Jewish philosopher but also the role of an ideal reader capable of accepting this contradiction and rising above it. In comparison with Deml’s books, the extant letters express a much less complicated and much more straightforward mutual friendship which stands out in Deml’s expansive epistolography thanks to its rare lack of ambiguity.