Ethnographic observation calls for a number of methodological procedures that allow any “careful” researcher to prepare and control the parameters of its investigation. However, it also draws from what is described as “grey areas.” While at times troubling, these grey areas of observation suggest highly reflexive dilemmas by which researchers try to normalize or maintain a degree of consistency in their approach. Through examples drawn from our own observational experiences and from other ethnographic research, this paper will address these “grey areas” of observation through a typology of three different troubles or dilemmas : delimitation, distancing, and identification. Without being exhaustive, this typology draws attention to the spatial (including the geographical, subjective and social) dimensions of observation.