This dissertation aims to explore West African transnational experiences in order to further understand how identity markers and politics manifest anxieties for transnational migrants and their movements between America and Africa. It engages and expands contemporary understandings of transnationalism with a focus on generational migrants. Generational migrants are defined as 1.5 through second-generation offspring of African immigrants. For the purposes of this research, "1.5-generation" is defined as an individual who was born in Africa and spent most of their lives in America, while "second-generation" is used to connote an individual who was born in America to African parents. Reflexivity, intersubjectivity, as well as identity negotiation and/or “code switching” are explored to explicate the experiences of generational migrants. Influenced by the theories and arguments of Stuart Hall, John Arthur, Joanna D’Alisera, W. E. B. Dubois, Pnina Motzafi-Haller, Audre Lorde, and Chandra Mohanty, this dissertation argues for a multiplicity and fluidity of identity (i.e.: holding multiple and sometimes contrary communities while constantly moving between continents), but also I am advocating for the possibility of fluidity in the reflexivity as one moves between these identity markers to create epistemological questions, constitute authorship, and expand representation. This argument is explored in each chapter via problematizing familial structures, African Fashion, ethnographic filmmaking, and auto-ethnographic writing. These contributions will transform the conceptualizations of African diasporic identities from one that is historically limited by bicultural formation into one that asserts the complexity of diasporic consciousness, which will construct new texts.