The subject of youth and masculinity is not the most popular linkage in the social sciences. Both terms give rise to a number of questions, debates, and ironies. There are ongoing disputes about the boundaries between these terms and how heuristic they are. Even the question as to how boys become men sounds primitive and absurd. On the other hand, the answers turn out to be so contradictory and confused that doubts arise as to whether it is even possible to explain the social placement, the process of maturation and development, by means of these concepts. In this article the author attempts to arrive at a partial answer to this question and, based on the materials of a survey, illustrates how one can make use of these concepts in sociological practice. This article is based on a collective study conducted in 2007 in the framework of a comparative project titled "Society and Lifestyles," in which the Region Scientific Research Center served as one of the Russian partners, and also on the basis of the author's research devoted to aspects of masculinity in youth groups. The focus of the present article is the gender approach to the analysis of youth identities, specifically practices of masculinity in youth groups. The thrust of the study focuses on youth groups, which are key agents in the socialization of young men and women. In this regard, as well, gender is one of the most significant identities, playing a decisive role in the lives of young men and influencing the character of their maturation. Survey data show that young males in Russia develop their sense of maleness from the set of social relationships and group experiences to which they are exposed, in addition to their personal life aspirations. (Contains 3 notes.)