This paper is an afterword to the articles by legal scholars M. A. Krasnov and A. P. Semitko published in this volume of Koinon. Based on the materials from these works, the author suggests a culturological vision of same-sex marriage problem. In his view, the main controversy of contemporary man’s life is the controversy between the past and the today-emerging future originated from large-scale comprehensive radical changes in the sociocultural world; between the old experience embedded in the traditions, norms, mental matrices, habits of culture and a new, currently gained experience that differs radically from the past and that forms new notions, values, modes of activities and human relationships. This new experience brings about yet-unseen perspectives for society and the individual but it also gives birth to a novel, yet-unutilized complexity, uncertainty of a future, often incomprehensible and even unpredictable risks and threats. The radical revolution of today’s mankind, thus, creates new complex challenges to society, man, culture on a daily basis. The problem of same-sex marriages in the given context appears to be one of the challenges generated by an accelerated evolution and the contradiction between the past and the future produced by it. An essential link of the paper’s concept is the reporting of an ambivalent significance of the cultural past generated by the accelerated development. On the one hand, it is perceived and works as inconsistent and therefore unnecessary for the present and the future, as an obstacle to the development of society and the individual. On the other, in the context of uncertain prospects and risks of largely unpredictable radical evolution, it acquires a new value as a reservoir of the life-tested experience, as an essential factor of society’s self-preservation in its anthropological and social specificity, in its regular, proven-in-practice relations with nature. From this point of view, the author treats a moderately conservative stance of M.A. Krasnov whose appeal to the Judeo-Christian moral origins of law, and, based on this, a critical attitude to same-gender marriage calls for a calm, balanced analysis of their possible consequences that are currently unclear, as worthy of careful consideration and useful in finding the best solution to the complex problem of same-sex marriages. Responding to this implicit call of Krasnov and, on the other hand, to the right antithesis of A.P. Semitko about the historical changeability of moral foundations of law, the author defines the most problematic zone of same-sex families: the socialization of children which, throughout all the preceding history, has been implemented by different-sex couples whose specific features and distinctions have largely determined the reproduction of the fundamental anthropological specificity of mankind and human race. That is why the emergence of same-sex parents cannot help being anthropologically essential. But there is a lack of reliable information about how exactly it is. Eventually, the author identifies three most significant aspects of the challenge posed by the problem under consideration: the challenge that requires thorough, comprehensive analysis of the experience obtained by same– gender families in the socialization of children; the challenge that requires joint efforts of proponents of different views and approaches to the problem and genuine dialogue between them, civilized discussion; the challenge that requires practical culture-making: finding and implementing a way to optimally solve the problem in a harmonious unity of the interests of individuals and society.