Queen Jelena is one of the most interesting personalities of Serbian Middle Age. She lived in Serbia from about 1250 to 1314, and took prominent role in Serbian foreign and internal affairs during the rule of Serbian kings Stephan Uroš I (1243–1276), Stephan Dragutin (1276–12829 and Stephan Uroš II Milutin (1282–1321). Jelena participated in the creation of Serbian politics towards West and Roman Catholic Church and ruled her own territories at Zeta, Trebinje, areas around Plav and Upper Ibar after 1276. The most interesting is her own close cooperation with both Serbian Orthodox and Roman Catholic Church. This paper considers two possible datings of her letter-oath to Dubrovnik – one in 1267–1268, and the other, after 1276. Different datings of the letter lead us to different interpretations of queen Jelena’s stands towards politics of her husband, king Uroš, and son, king Dragutin.