The available research findings believe that the resource and emotional connection between the second generation of migrant workers and their parents is close. Through the urban and rural multi-sited ethnography of the coastal industrial zones and the inland migrant workers’ sending areas, this paper finds that it has formed a new type of “alienated” intergenerational relationship between the older single male workers of the second generation and their parents. The analysis also shows that the establishment of such relationship has gone through three periods: the relative intergenerational independence in the early part of the working life, the intergenerational conflict in the difficult period of marriage, and the stagnation of the exchange of resources and emotions and the alienation of the relationship during the hopeless period of marriage. Behind this kind of intergenerational relationship are the opposition of intergenerational family goals, the lack of family cooperation, the separation of work and living space, and the rupture of intergenerational bonds caused by these factors. This intergenerational relationship shows the multiple aspects and multiple paths of the family structure transformation in the process of urbanization. The older single male workers have become a kind of individual families separated from family cooperation, and they have also become potential new urban distressed groups.