This chapter is about young men’s desire to belong through economic exchanges amid their struggles to become autonomous individuals. The ethnographic case studies from Cape Town, South Africa, show how hustling made young men feel a sense of belonging across the divides of race, class, and gender. Although it assumed different meanings among White, Colored, and Black men, belonging was always tied to overcoming individualism through reciprocity and the provision of goods and skills. Hustling was not just about making money in the face of poverty and social exclusion. It included empathy that was tied to a positive sense of manhood through responsibility in moral economies. In local assemblages of masculinity, hustling was also about becoming a resourceful male patron and provider, particularly in relation to women. But access to social networks and material goods in the postapartheid city was limited and constrained young men’s sense of belonging. And the less belonging the men felt, the more they tried to be in control, and the more they potentially took advantage of others, particularly female peers and partners. This sometimes contradicted the ideal of manhood as an act of service to others and spurred men’s sense of disempowerment under democracy and its policies of gender equality.