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The present research aimed to assess and compare the perspectives of teachers, parents, and youth regarding the main positive aspects and concerns they have about youth in Macao, namely: (1 and 2) What are the main positive aspects/concerns Macao teachers, parents, and youth focus on? And (2 and 3) How aligned are teachers, parents, and youth in Macao regarding the positive aspects/concerns? We applied a quantitative methodology based on a quantitative content analysis of open-ended questions included in the Macao validation (Simões et al., Unpublished report) of the Achenbach System of Empirically Based Assessment (Achenbach, 1991; “what are your concerns regarding your child/your student/yourself”, and “what are the most positive aspects about your child/your student/yourself”). We found alignment regarding positive aspects, with youth, parents and teachers focusing on personality, abilities, and attitudes, and parents additionally on independence. Regarding concerns, there was less alignment. All mentioned academic performance and interpersonal relationships, but parents and teachers also mentioned health, morality, attitudes, and teachers’ class engagement concerns. Teachers and youths mentioned future planning, while only the youth mentioned school activities and facilities, their abilities and character and class rules and assignments. These categories are aligned with development models, including ecological systems theory (Bronfenbrenner, 1994), social learning theory and social cognitive learning theory (Bandura, 1977, 1986), moral development perspectives (Mead, 1928; Gilligan 1933), self-determination theory (Deci & Ryan, 2000) and positive youth development perspectives (e.g., Lerner, 2005). The main practical implications are that (1) youth should have a greater awareness of their physical and mental health; (2) parents should build up a support system to enhance autonomy (3) schools play a crucial role in promoting students’ health by creating a supportive environment; (4) counsellors should promote re-connection between youth and their parents or teachers; and (5) decision-makers should invest in mental health education awareness to diminish the stigma, de-emphasise education strategies based on standardised testing, and address broader social and economic inequalities to reduce disparities and academic pressure among youths, parents and teachers.