This study seeks to understand the challenges encountered by qualitative researchers while investigating sensitive topics. We make a valuable contribution to the existing literature on researcher well-being and the mitigation of potential adverse incidents during data collection in studies on sensitive topics. The researchers maintained a comprehensive diary while conducting a study on the sensitive topic of work-family conflict among Indian working women. The analysis of these diary entries revealed three primary categories of challenges: (a) emotional challenges encompassing emotional sustenance, self-awareness, the element of care, building rapport, reciprocity, breaking the connection, preparing for exit, and researcher exhaustion; (b) methodological challenges, including data recording and interview location; (c) ethical challenges, such as confidentiality and guilt; and (d) other challenges, such as establishing credibility as a mainstream researcher in academics. This study aims to raise awareness about the challenges that qualitative researchers face, offering insights into potential dilemmas and explaining how reflexivity, self-disclosure, reciprocity, and a well-planned exit strategy can assist in navigating and addressing researcher biases.