Transnationalism and border studies have often rightly focused on the movement of people, materials, and ideas across national lines as well as issues of migration such as along the U.S.-Mexico border. This thesis examines the concept of border crossing from a different angle, where rather than looking at the movement of people across a national border, I examine the social borders crossed within the context of massage cupping therapy, a medical form that itself has traversed borders. My research revolves around a Mexican massage therapist, who frequently travels between the state of Texas and her home in the state of Nuevo Leon. She maintains a large pool of clients in both places. The Texas clients are mostly working-class migrants from Mexico, while the Mexican clients are wealthy Mexican citizens, most of whom own multiple businesses. My findings primarily focused on the interactions during the massage encounter, and acknowledge Teresa’s unique approach of communicating with her clients. Additionally, in examining these interaction, I also found that this massage healing practice, which literally crosses the U.S. Mexico border, also crosses social and metaphorical borders of class, intimacy, mind/body, and traditional/modernity. My overall argument is that in crossing different social borders, this practice emphasizes the massage healer’s flexibility in being able to fit in and create meaningful experiences for clients in two very distinct social contexts. This argument can be extended out to consider the benefit in flexibly crossing border and social categories that structure hierarchies. This thesis adds to existing bodies of anthropological literature on transnationalism, and border crossing, by reaffirming how borders are complex and demonstrating how different, more metaphorical borders can all be crossed within a single cultural practice, in this case massage healing encounters.