This study explored the family context, the parent-adolescent relationship, and the ways in which Canadian adolescent youths conceptualized, understood, and viewed self-criticism and self-compassion in their everyday lives. Ten immigrant youths (five Filipinos and five Africans) aged 12-18 years old, were interviewed about feeling down, disappointment, failure, as well as the ways in which they felt or experienced positivity and their relationships with their parents. Qualitative thematic analysis was used to analyze the youths’ responses. The youths discussed a broad range of concepts, views, and ideas connected to self-criticism, self-compassion, and parent-adolescent relationships including re-focusing to an optimistic perspective during tough times, negative states of laziness and overthinking, conflicts with peers and parents and how these stresses are internalized and felt, feeling consumed by sadness and mistakes, anger and regret from mistakes, acknowledging distresses as temporary, feeling heard and understood by their mothers, and speaking to fathers only when permission was required.