Dating apps facilitate connections with strangers, yet inherently involve uncertainty, requiring users to continually assess others’ trustworthiness. This study investigates how individuals seeking intimate relationships navigate trust-building processes in the context of dating app interactions. Semi-structured interviews were conducted with 10 users to examine strategies across different stages of relationship development. Findings reveal that in the pre-interaction stage, perceived authenticity—based on photos, self-descriptions, and chat content—plays a critical role. Upon transitioning to offline encounters, users assess the consistency between online portrayals and in-person behavior as a primary criterion for establishing initial trust. As relationships progress toward greater intimacy, deleting dating apps functions as a symbolic act of commitment. Nevertheless, the ease of app reinstallation and the retention of stored user data continue to raise concerns about partner fidelity. This study highlights the evolving nature of trust in digitally mediated intimacy and underscores the socio-technical tensions between algorithmic convenience and emotional security in contemporary relationship trajectories.