The special attention of this paper is centered on Czech adolescents during a decade of political, economical, and social changes (1992 and 2003). We summarized results of two projects. The first one was a based on empirical research comparing data collected in 1992 and data collected 2001. Both samples were reported in regard to their daily activities, future expectations, daily problems, and well-being. The second project is four-year longitudinal study (1999-2003). This research was broadly oriented on peer, family, and school context of the adolescent psychosocial development. Compared to generation of adolescents from the beginning of nineties, the present generation has grown up in a democratic society, and post-totalitarian, post-communist influences are not evident in their everyday life. As empirical results indicate, their greater need for stability, rules, and positive norms correspond with their reported higher level of commitment. Compared to the post-totalitarian generation, this generation is more aware of their own needs and desires. They seem to be more pragmatic, less optimistic and more realistic in respect to their future. Not surprisingly, they are more satisfied with their present lives and future options.