This study employs a relational dialectics approach to gain insights into the nature of relational communication via Cyworld, a Korean social network site. Qualitative analysis of in-depth interview data from 49 users suggests that Cyworld users routinely negotiate multiple dialectical tensions that are created within the online world, transferred from face-to-face contexts, or imposed by interpersonal principles that relate to Korea’s collectivistic culture. The interviewees experienced a new relational dialectic of interpersonal relations versus self-relation, analogous to Baxter and Montgomery’s (1996) connection-autonomy contradiction. Their responses suggest that Cyworld’s design features and functions encourage users to transcend the high-context communication of Korean culture by offering an alternative channel for elaborate and emotional communication, which fosters the reframing of relational issues offline. Cy-Ilchons (online buddies) virtually extend the Korean cultural concept of blood ties, called yons, in ways that intensify the openness-closedness contradiction at early stages of relationship formation.