New media technologies are ubiquitous. Among these, digital games continue their rise in significance, constituting a visible domain within which people learn and develop specific sets of skills and practices. This study addresses a lack of research into the socialization experiences of new media technology users. I explore how participants experienced socialization into two digital games that they had never played before, World of Warcraft and Portal 2. Using a symbolic interactionist approach and an array of qualitative methods such as observations, talk-aloud protocols, audiovisual recordings of gameplay, “gameplay reviews” and in-depth interviews, I extracted rich data from the gameplay and interpretations of eight university student participants who each played approximately 20 hours of each game. Players engaged in micro-level meaning-making processes through which they made sense of the virtual environments. I outline a process of gameplay socialization that organizes the development of meaning-making over the course of their participation, and show how players had varied socialization experiences. A significant portion of their gameplay was spent interacting with digital objects, some of which became significant others. Such human-object relationships can be complex and social, and digital objects are major agents of socialization into digital games. Complexity in digital games rises with the potential addition of human interactants, and I analyze player-to-player interactions in cooperative and conflictual situations to show how players socialized one another in terms of game rules and social norms. Finally, I discuss some methods players developed to pragmatically handle increasing complexity in terms of outcomes of gameplay socialization. Analyzing gameplay socialization provides insight into the significance of user experience with new media technologies, which has implications for media creators and users. Being attentive to user experience increases reflexivity in media development and use, as well as enhances communication between creators and users.