The article concerns the problem of developing online technologies for adolescents’ career guidance and professional consultation with regard to their huge interest in computer programs (games and other entertainments) on the one hand, and the apparent lack of science-based computer methods of professional self-determination, on the other hand. We analyze the positive and questionable aspects of the design and the practical use of online technologies in professional counseling compared to existing technologies used in the professional consultation. We also consider the capabilities and limitations of these online technologies in solving the basic problems of vocational guidance (information, diagnostic, moral and emotional support of the client, assistance in decision-making and career planning). For example, the development of the author's methodology of “Choose and Go” designed for adolescents’ online use, shows the problem facing the designers of such software products, solutions to these problems. The basic ideas of this methodology are: comprehensive assessment of select work on the basis of full consideration of the psychological structure of the work; the use of expert assessments of the extent to which components of professional activity correspond to the official list of the integrated groups of specialties; the use in the modes of the real and online professional counseling; the account not only the desires of a teenager, but his/her current and potential abilities.