The recent and rapid increase of Internet culture and new communications technologies is one important facet of changes in contemporary social life. Understanding the multiple and complex nature of these changes is an important sociological question. This paper uses qualitative data gained through face-to-face interviews and technology-mediated interviews conducted with college-aged students to explore the ways in which Internet culture and digital socialization affect youth relationships and sociability. Previous research has suggested that the pervasive and intensive use of Internet in education, communication and entertainment may be leading to decreasing face-to-face interaction among youth. Other research focuses on how technology may also expand and transform sociability by allowing people to communicate with a wider and more diverse network of people. Due to the contradictory findings about the consequences of widespread use of Web 2.0 technology among youth, the goal of this research is to explore the depth of the effects that digital socialization has on youth relationships, sociability, connectivity, and identity formation.