This article is a reflexive account of an ethnographer’s foray into digital anthropology, necessitating the formulation of collaborative research strategies. The information presented comes from yearlong fieldwork among blogshop owners and commercial bloggers in Singapore. This paper is part of an ongoing doctoral dissertation that looks into narratives of self-creation, boundaries of privacy, and vicarious consumption, and is the groundwork for the continuation of more extensive and in-depth research. The exploration between August 2011 and December 2012 reveals the need for anthropologists to assess their digital community before entering the field in order to access the community with tact. It further shows some defining features of this digital community that contributed to the shaping of the research methodology. I also analyse three points of contention born out of bringing online communications and relationships into a physical space offline. They are the ambiguous transference of intimacy, verbalizing cyber lingo, and the place of online media in face-to-face communication. Collaboration is a defining feature of this digital ethnography’s methodology given the extent of networks and partnerships across a vast array of locations, vocations, and demographics throughout the community.