This chapter applies the 5Cs model of PYD comprising competence, confidence, character, connection and caring among 1403 youth (M = 18.91 years) in Bulgaria (n = 196), Italy (n = 354), Norway (n = 564) and Romania (n = 289). These countries offer a novel and unique context to apply PYD as related comparative work with youth samples is rare across Eastern (Bulgaria and Romania), Southern (Italy) and Northern Europe (Norway). Further, Bulgaria and Romania are emerging nations following the collapse of the communism in late 1980s in contrast to Italy being a traditionally patriarchal country and social equity driven Norway. The chapter presents an empirical example that evaluates the factorial structure and measurement invariance (i.e., the degree to which the scale measurements conducted across different populations exhibit similar psychometric properties) of the 5Cs model. The results of confirmatory factor analysis (CFA) supported the 5Cs as well as a second-order 5Cs of PYD factors, suggesting that the 5Cs model is a reliable and valid measurement tool in the four European countries investigated. The chapter concludes with an exploration of relevant implications for research, policy, and practice.