Positive Youth Development (PYD) addresses young people from their potential, strengths, and assets, in contrast to the deficit view that focuses on their weaknesses. The PYD model promotes constructive behaviours in youth by underscoring positive attributes usually found during the transition from childhood to adulthood in order to foster healthy development. In a nutshell, PYD comprises five key competence (5C), forty developmental assets, and the flourishing model. In the present study, 261 participants were approached by an online survey (nWomen= 189, nMen = 72, MeanAge= 22 years old), as part of the Cross-national project on PYD (CN-PYD), which included several measures, among which those included in the research were: The Developmental assets Scale, the Short-form of the Five Cs, and the Mental Health Continuum Short-Form (MHC-SF). Emotional, Social, Psychological and General Wellbeing scores were tested on the premise that females would score significantly lower than male participants (H1). In addition, two multiple regression models were tested with the first wave of the Chilean PYD project on the premise that Positive Identity, Confidence, Character, and Connection would predict the variance of General Wellbeing (H2), and Psychological Wellbeing (H3). The findings provided total support for H1 and H2, and partial support for H3. Overall, the research complements previous investigations conducted with Latin American and Chilean Youth, stressing the importance of researching Latin-American adolescents’ developmental assets, PYD competence, and the varieties of subjective wellbeing.