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Little to no extant scholarship examines procedural, epistemological aspects of conducting intergenerational oral history interviews with Black elders. Thus, in this multivocal piece, we, two Black women oral historians of education, discuss specific tensions we navigated in our respective projects that focused on Black baby boomers’ educational experiences in the US South. The baby boomer generation encompasses those born between 1946 and 1965, and our disparate studies, on which we draw here, sought to investigate how they remembered their raced, classed, and gendered educational experiences during the 1960s and 1970s. In our research processes, issues around identity arose, and this paper pursues two areas of inquiry related to those issues—trust and relationship building with narrators and race as an all-encompassing metalanguage; we contend this metalanguage superseded narrators’ perceptions of gender’s influence in their lives. It is our wish that our transparent reflexivity aids other scholars in wrestling with considerations similar to those we found ourselves navigating.