The Serbian princess (despotica) Jelena Mrnjav evi (c. 1349-1404), later known as the nun Jefimija, was a noble woman whose great piety and artistic talents inspired the creation of a number of precious devotional objects. The focus of this thesis is a small enkolpion diptych, a pendant icon, 1367-71, that was originally presented to Jelenas son Ugljea Despotovi on his christening day by the Metropolitan of Serres, Teodosije (c. 1366-after 1371). When Jelenas son died prematurely at the age of four, the mother composed a poem expressing her sorrow over the loss of her son. The poem was engraved on the back of the diptych. The diptych resides in the Hilandar monastery, Mount Athos, where Jelenas son is buried. The purpose of the present study is to discuss the iconographic program of the diptych and examine the meaning of this iconography and Jelenas literary composition in relation to the different contexts in which the Metropolitan and the Mrnjav evi family found themselves.