Nowadays, algorithm-driven platforms have emerged as novel mediators to facilitate connections among strangers. Yet, the would-be dilemmas concealed behind “precise matching”remain understudied. This research investigates the phenomenon of “offline dazi-seeking” among rednote users through multi-round participatory observations and in-depth interviews, analyzing its predicaments and underlying causes using grounded theory. The research reveals that these dilemmas stem primarily from seekers’ misaligned perceptions of strangerships: pragmatists expect accelerated intimacy that bypasses conventional social rituals of acquaintance, whereas romantics struggle with strangers’ ambiguous positioning between intimacy and detachment. These predicaments originate from the flexible social context shaped by technological and cultural forces: algorithmic environments amplify serendipity and perceived similarities, constructing imagined compatibility, while offline encounters expose mismatched perceptions and divergent habits, triggering relational tensions. Notably, individuals’ relational cognition manifests not as progressive “uncertainty reduction” but rather as “certainty-uncertainty oscillation.”Conceptualizing “dazi” as “event-based relationships” (shiyuan guanxi), distinct from “interest-based relationships” (quyuan guanxi), the study advances theoretical understanding of algorithm-mediated sociality and contributes to broader debates on the reconfiguration of stranger interactions in the platform era.