In this article, we address negotiating interactions with hesitant participants who are public figures, yet do not traditionally fit within the category of the advantaged. We target new field researchers and rusty veterans by offering an applied approach to: (1) preparing for the field; (2) managing interactions with hesitant participants via finding common ground while drawing lines, connecting with key informants, and expanding on public information; and (3) working through failed interviews. We discuss the importance of power relationships, positionality, and ethical standards, particularly in relation to negotiating similarities and differences between researchers and participants.