How young people think of themselves as humble plays a critical role in their ability to read the minds and emotions of others and engage in social interactions. This study explored the interconnections among mindreading, humility, and social anxiety in adolescence. Adolescents 11-18 years (N=326; 167 female, 145 male, Mage= 14.57, SD = 2.37) completed on-line tasks to measure mindreading or Theory of Mind, and self-report questionnaires on humility and social anxiety. Results showed that one's ability to read the minds of others increased throughout adolescence, although feelings of anxiety and fear around others remained consistent throughout the teenage years. Proficient mindreaders were more likely to hold high perceptions of humility, and experience different feelings of social anxiety around others depending on their gender. Separate gender mediation analysis showed that high levels of mindreading related to high levels of humility and social anxiety for girls, but low social anxiety for boys. The present findings contribute to research on mindreading, humility, and social anxiety, and hold implications for positive youth development and gender-sensitive social-emotional learning programs. Results extend theoretical models of adolescent development by clarifying the dual role of humility, and suggest new directions for intervention strategies that promote healthy social self-concepts in youth.