This paper draws on the story of "Mikael", a schoolboy from northern Finland, to examine how his affective ties of compassion and his pursuit of dominant forms of masculinity evolve in his journey from middle childhood to young adulthood. In his earlier years, Mikael's speech regarding his relationships with peers and family members indicates a non-hierarchical sympathetic orientation, enabling sensitivity to diverse vulnerabilities. Over time, his speech reflects more and more the ideals of dominating masculinity and hierarchical relationality, and it is marked by "inner-circle" compassion that excludes people considered vulnerable and/or "Other". The authors argue that the challenge of balancing compassionate concern, masculinity and social position generates heavy costs, imposing on young men not only the heavy burden of fulfilling the requirements of culturally esteemed masculinity, but also a partial loss of being in touch with one's inner faculties of emotions and imagination.