This paper addresses Lincoln's [2010. "'What a long, strange trip it's been …': Twenty-five years of qualitative and new paradigm research." "Qualitative Inquiry" 16, no. 1: 3-9] call for greater attention to the question of rapport in qualitative research through a reflexive examination of researcher-participant relationships in two qualitative studies with urban teachers. In these projects, one a series of case studies and the other an ethnography, we as researchers found ourselves offering various forms of support to struggling teachers in challenging circumstances. These close relationships provided insider data but also raised ethical questions about the boundaries of the Self-Other conjunction. We present three dilemmas from our research in which we struggled to identify the boundaries of support, validation, and friendship in qualitative inquiry. We conclude by re-framing the static notion of rapport as a dynamic and shifting negotiation between a researcher and a participant and expanding the definition of rapport to include legitimate means of support.