This chapter projects possible human futures with robot sex workers (RSWs). These are models of robots with integrated capabilities designed to enhance human sexual pleasure. Using attachment theory as a framework, concrete questions about what might constitute human-robot sexual and emotionally intimate relationships are presented for discussion, including design and cultural issues. Mori’s Uncanny Valley theory is used as a springboard for a new model to include temporal and cultural influences on people who interact with robots, the Robot Accommodation Process Theory (RAPT). Finally, the ideas of how RSW will be normalized into individual human-robot relationships as well as how the relationships will be valued by culture over time are used as a premise for building theory in the areas of meaningful and affectionate human-robot relationships.