The phenomenon of ken lao embodies the structural tension and intergenerational ambivalence in transitional Chinese families. Two kinds of families in Shanghai that rely on parents are compared, including attitudes, response strategy to ken lao, and the impact on the intergenerational relationship. In order to discuss the coexistence of conventionality and modernity in today’s Chinese family life, the interaction and tension among the pursuit of material goods, values, and affect are analyzed. The findings of this research suggest that the reflexive change in urban families has not resulted in familial individualization. On the contrary, the ethics of intergenerational responsibility have been reconfigured in individual reflexivity and negotiated practices. The emotional structure of parent-child unity is strengthened in the transitional society, which contributes to the strong cultural resilience of the tradition of intergenerational cooperation.