Dialogue has become an important principle of communication with the world for the Orthodox theology in the West. Orthodox thinkers, who found themselves in Western societies that were predominantly secular or Protestant and Catholic, sought the ways to witness their faith to the world and remain connected to the others in the same time. So, many of them independently resorted to a dialogue as a mean of building bridges. Metropolitans Kallistos Ware and Anthony Bloom were most prominent Orthodox thinkers in the United Kingdom in the 20th century. They both were active supporters of dialogue, either ecumenical or with secular society. However, they explained the need for dialogue with different theological assumptions. Metropolitan Kallistos Ware, in general, was an adherent of the Orthodox kind of dialogical personalism that presupposes that a human being as the image and icon of the Holy Trinity becomes the real personality only in relations with others. Considering this and other reasons, he opted for ecumenical and inter-Orthodox dialogue. Metropolitan Anthony, though supporting dialogical personalism as well, put main emphasis on common faith in Christ and human dignity, when he spoke about ecumenical dialogue or dialogue with secular society respectively. In other words, he suggested as primary standpoint for the dialogue that all Christians believe in Christ, while all people of good will believe in a man and seek for common good. In my paper, I will analyse the reflections of these two prominent Orthodox bishops on dialogue in detail and try to figure out their relevance for the challenges of the present day (inter-Orthodox tensions, growing fundamentalism and secularization).