This chapter explores the pervasive narratives of authenticity, self-expression, and realness that structure activity in the social media sphere. After all, many social media producers articulate the importance of expressing themselves “authentically.” Hence, the chapter considers what social media producers mean by “authenticity,” “realness,” and “relatability.” In addition, this chapter examines how these definitions vary within and across intersectional social categories, and to what extent these ideals guide the production and promotion of creative content. Finally, the chapter looks at the ways that aspirational laborers aim to resolve the tension between internal compulsions and external demands, given that the “authenticity” trope is increasingly compliant with the demands of capitalism.