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Demographic and health surveys in the Philippines have shown a rise in cohabitation among young people. This chapter aims to provide an in-depth sociological understanding of a more specific phenomenon called serial cohabitation – referring to the dissolution of current cohabitation and entering a new one, and the continuation of the cycle if the new one ends again. By developing the framework of undisplaying and re-displaying family from Janet Finch’s displaying family, this study posits that serial cohabiters experience a cycle of wanting to display an ideal family and having to undisplay every time the dissolution of the cohabiting relationship happens. This study demonstrates how serial cohabiters with children, in response to social stigma, exhibit resiliency toward stepfamily formation and committed sexual relationships. This chapter, therefore, conceptualizes “family acceptance” which refers to embracing the fluidity, reconfigurations, and “imperfections” of their newly formed family and “community acceptance” which covers the same affirmation from friends, neighbors, and extended relatives who are considered as relevant others by serial cohabiters. Family acceptance comes in three forms: first is the acceptance of/by children, second is the acceptance by the parents to the repeated stepfamily formation within their own homes, and third is the acceptance of the woman herself to the possibility that cohabitation is the “happy ever after.” This study argues that once these forms are achieved, serial cohabiters become more capable of undisplaying their previous family and displaying their new family.