As digital media become part of peoples’ experiences and practices of love, moral tensions arise from contradictions between existing and emergent norms and practices of intimacy. In this chapter, I look at moral tensions arising from the practice of digital media surveillance in romantic and conjugal relations. Using the case of working-class Filipinos in Metro Manila, the study examines the practice of sharing passwords in the Philippine context where it is seen less as a gesture of intimacy but more as a sign of distrust. I aim to identify the moral tensions generated by digital media surveillance and explain how they affect trust in intimate relations. Based on ethnographic data, I find that sharing passwords indicates the transactional nature of trust in a digital media environment where intimate relations become uncertain. Building trust through partner surveillance or transparency comes in conflict with moral expectations of autonomy and privacy among working class Filipinos. However, ethnographic examples also reveal that intimacy can be sustained under watchful eyes of lovers.