Largely due to their colonial past and neocolonial present, Filipinos have been receiving certain messages for generations regarding their heritage and the Western culture, and have been facing constant tensions and struggles between the Filipino and the Western, and the individual and the collective. This constant push-pull between Filipino and Western cultural values shape and are reflected in Filipinos’ daily lives, interactions with each other, and interactions with the rest of the world. To this end, this article discusses a wide range of factors pertinent to Filipino Americans—from immigration, family structure, and values, to parenting, gender roles, and intergenerational issues—to convey that these factors need to be understood in the context of colonialism, its legacies, and its contemporary implications when conceptualizing Filipinos Americans’ experiences. We also provide a discussion of Filipino values that go “beyond the surface” as we talk about the core Filipino value of kapwa, and how ethnic identity, acculturation, and cultural conflicts among and between Filipinos need to be conceptualized through kapwa. Then, we discuss how colonialism and its most insidious legacy—colonial mentality—may influence kapwa, acculturation, ethnic identity, and Filipino American families. We end with some recommendations for researchers and service providers, with the hope that a historically informed and sociopolitically contextualized understanding of Filipino Americans will be helpful to those who work with this population.