This study examines how Taiwanese college students understand the traditional, culturally Chinese concept of Yuan and its role in their use of a new and distinctive Taiwanese social networking site—Dcard. Particular attention is paid to the Dcard’s unique friending mechanism, which provides users the opportunity to connect (or not) with one, seemingly random new friend each day at midnight. Through thematic analysis of 15 semi-structured long interviews, the study finds that Dcard users understand Yuan as a multi-faceted concept pertaining primarily to interpersonal relationships (relationalism). Users perceive Yuan to influence relationships in a predetermined, causal fashion (fatalism), but they still assert some agency in their relationships (controllability), including their ability to believe deeply in Yuan. Users perceive Yuan to play an important role Dcard use, and the concept’s different facets each influence key moments in the friending process—from receiving a friend recommendation, to the choice of whether to accept or reject that request, to the initiation and maintenance of relationships through Dcard. Dcard’s architecture, including elements of randomness and partial anonymity intensify the experience of Yuan. This study underscores the importance of studying how cultural concepts like Yuan are socially constructed and used in online contexts. More, it illustrates how social networking sites can use design and architecture to tap into culture to attract and retain users.