As is widely observed, social network sites (SNS) constitute a new environment of interaction where users encounter various challenges that they usually do not encounter in other environments. This study aims to provide an in-depth understanding of how users deal with the challenges in this unique environment, paying particular attention to the ways in which they examine and reflect on their social ties and networks. On the basis of 36 semistructured interviews with Facebook users, the article presents the hypothesis that participants of SNS develop a tendency to become highly observant and inquisitive about their networks and are frequently involved in an activity that the authors call analytic labor. © 2013 International Communication Association.