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The thesis is focused on the possibilities that exist for crossing or even transcending the boundary between existence in the real and virtual worlds, and it presents the findings of a longitudinal study of an online community of cigar smokers, which was created for the needs of the study, tracing the interactions of its participants over a period of eighteen months. The internet enables the formation of online communities that provide unprecedented opportunities for communication across geographic, political and economic divides, and reach across barriers of distance, time and culture. Such communities provide a space for people to come together based on existing friendships, common interests, their work, and a variety of other factors. The study is aligned with the literature that views online communities as social networks, and such a way of thinking enables us to understand the relationship between structure and dynamics, and reveals the different roles of the participants, their relationships, as well as the structure of the social system that underpin the observed development of online communities. Network analysts suggest that offline relations affect the online interaction of participants; the ways in which that occurs, however, is still left unanswered. Although the literature suggests the need for more longitudinal studies on the role of online communities in creating novel interaction channels for both networks and individuals, there are very few to date. Moreover, the literature has mainly focused on the structural specifications of networks, and has paid scant attention to the content of the conversations that connected individuals are having. Hence, a longitudinal study with a focus on communicative processes is needed, to provide a focus on networks, people, and processes. To elucidate the understanding of offline interactions, the study explores an online community of cigar smokers, and traces such interactions identified in the content. The online community was created for the needs of the study, and populated through an online invitation system to track the initial relations among participants. The novel methodological approach of the study combines social network analysis with content analysis to generate a more nuanced account of the emergence of roles and relationships associated with recorded activities and observed structural features of the social networks, and explore the relationship between online and offline interactions. The study identified six distinctive technology-driven social trends that affect the emergence and evolution of networks among the participants. The distinctive patterns of interaction that persist over the course of the study are associated with a mix of behaviors that include play, trading and gifting, and entail the exchange or flow of informational and material objects. The findings of the study reveal that the participants of the online community used metaphors, puns, words from the everyday life repertoire, as well as the coining of new words, in order to communicate regarding such interactions. The diversity of activities across the community, and the flow of information, cigars, and money demonstrate the potential for complex, multi-faceted socioeconomic spaces that bridge the divide between virtual and embodied space, informational and material goods, and social and economic transactions. Moreover, the findings of the study shows that the offline interactions among the participants of the online community gave rise to a dense network of a homogenous population, with the properties of a scale free network, and of a small world with three degrees of separation. The interactions among the participants were highly reciprocated and reinforced, contributing to the growth of the network over time, and the tendency of participants to connect with friends of friends is equally spread in the network and not affected by prominence. There is a positive and statistically significant rich-club effect in the network, showing that the prominent participants do not compete with each other for status, rather they tend to interact with each other. The growth of the network can be divided into two periods: an initial accelerated growth, and an equilibrium period of homogenization of the population. During the initial accelerated phase, the backbone of the network is established, which contributes to the stability in shortest-path based metrics over time, and the overall density of the network. The findings suggest that we should treat with caution conclusions that relate differences in status to differences in network position. Although hubs in a network can control the diffusion of recourses across the entire community, the unstable nature of such positions suggests that the participants do not hold them indefinitely, and these positions offer only a temporary advantage to those who posses them. Furthermore, it is unclear to what extent individuals can strategically manipulate their positions in a large network, even if that is their intention. The findings of the study illustrate the value of combining network analysis and content analysis to understand the evolving structure of online communities and their offline extensions. The study provides academics with new insights regarding the interactions of participants of online communities, and open new avenues for future research on the topic. Bridging work remains at the core of making sense of social experiences online, and the findings of the study contribute to the literature on online communities by responding to calls for more studies to make sense of the relationship between the online and offline activities. Moreover, this study contributes to the broader Information Systems literature, and more specifically to the field of Computer-Mediated Communication, by elucidating the evolving social interactions amongst participants of passion-centric online communities. When it comes to practitioners, the findings of the study here can provide the managers of online communities with novel insights on how to study and understand the communities they manage, identify opportunities or problems, and deliver policies and interventions in networked forms. Furthermore, the findings of this study can enable the managers of online communities to think of innovative ways to enable the participants to engage in offline interactions, without the fear that such interactions will negate the sustainability of the online community, while by enabling them to engage in such interactions, they can build more robust and successful online communities.