The advent of positive psychology has increased awareness of factors that lead individuals to thrive in life, allowing for a more comprehensive model of mental health service delivery. However, while measurement and understanding of character strengths and well-being have improved over the last decade, the interaction of these factors with social risk factors is not entirely understood. The current study analyzed an archival dataset consisting of self-report data from 425 high school students, to examine the extent to which high school students' specific character strengths (i.e., social competence, self-regulation, responsibility, and empathy) are associated with positive psychological outcomes (i.e., gratitude, life satisfaction, and hope), and moderate the relationships between positive psychological outcomes and relational and overt peer victimization. All measured character strengths were positively associated with life satisfaction and hope except for empathy, which was negatively associated with both in multivariate analyses. Social competence and self-regulation were positively associated with gratitude. Relational victimization (but not overt victimization) was inversely associated with life satisfaction and gratitude, and indirectly predicted hope as mediated by gratitude. Gratitude and hope predicted life satisfaction in both models, and served as partial mediators of character strengths and relational victimization. For overt victimization, social competence served as a protective factor and self-regulation served as a risk factor to gratitude. For relational victimization, self-regulation served as a protective factor to gratitude. Implications for research and practice are discussed.