The benefits and challenges of insider positionality have been much written about in relation to qualitative research. However, the specific emotional implications of insider research have been little explored. In the article, I aim to bring the literature on insider positionality to the study of emotion in qualitative research through a reflection on my experiences as a “total insider” conducting interviews for a longitudinal qualitative study examining mental health during the transition to parenthood among sexual minority women. On the basis of this experience, I highlight emotion-related benefits and challenges of my insider positionality, as they pertain both to the quality of the research and to my personal experiences as a qualitative researcher. In particular, I examine the potential benefits of my insider positioning for establishing rapport and my capacity for empathy, and the personal emotional growth and learning that my insider positioning made possible for me. With respect to challenges, I examine how my emotional investment in the researcher-participant relationship influenced my role as a research instrument, and discuss the difficulties I encountered in managing appropriately boundaried relationships and making decisions about self-disclosure. I close by highlighting promising avenues for further exploration of the emotional implications of insider research, from the perspectives of both researchers and participants.