Adolescence is a complicated, full of challenges and explorations period in life on the way to adulthood. The behaviour of adolescents is considerably re-configuring under the pressure of biological, psychological, and social transformations, and the internalization of community rules and values, as well as the adoption of desirable behaviours, is not always easy or successful. During adolescence, anomie can easily become an attractive status quo, but it can also evolve, however, relatively easy, to delinquency. This exploratory study, part of the Planet Youth project, is based on an analysis of 17 items from a questionnaire applied to a sample of 2,694 young people in Bucharest, Romania, in 2018, high schoolers in grades 9-11. The main objective of this approach was to assess the impact of some socio-cultural factors regarding school, family, peer group, and neighbourhood on the adoption of deviant and delinquent behaviours among Bucharest teenagers. For data analysis, two dependent variables were built by aggregating items in the questionnaire: the level of anomie (composed of 8 items) and deviant behaviour (composed of 17 items). As independent variables, 17 predictors composed from 67 questions from the questionnaire were used. The main results reflect a high level of anomie among the adolescents of Bucharest and a low level of deviance, and a weak link between these two variables. On the other hand, adolescent anomie and deviance are favoured by anger management, perceived peer attitudes to substance use and digital leisure, together with low parental surveillance.