The chapter describes, with two ethnographic cases, how hegemonic masculinity exerts influence during teenage boys’ formative years and their responses. There is a focus on failure or inadequacy, rather than the usual accounts of hard work and academic success in related Chinese literature. The boys' perceived docile and unmanly characters concern their parents, but the boys choose to exercise their agency to develop alternative masculinities, including interpreting androgyny and effeminacy as desirable male models, rather than conforming to the hegemonic ideal. The one-child policy and volatility created by the countrywide rural-to-urban labour migration are identified as affecting the lives of boys in 21st century China and leading, amongst other things, to large numbers of left behind children and only sons.