Various science and technology studies (STS) scholars argue that users are active agents who provide insight in the uses of a technology. While researchers describe the effects of technologies like the Apple iPod as isolationary, few focus on how users form social connections. In this study, I argue that contrary to assumptions surrounding iPod usage, the ways personal technologies are used and the cultural impact usage has on everyday interactions allows for the formation of social connections in practice. Drawing upon fifteen in-depth interviews and four observations, a modified grounded theory approach was used to analyze the meanings users gave to interactions with the iPod. Findings indicate that users experience social connection through file sharing, ownership, and collective usage, which coexist with processes of creating isolation. This demonstrates that the meanings given to the use of a particular technology are not stable, but interpretively flexible and contingent on social context.