In 2014, I embarked on a small qualitative study to examine, for the first time, the well-being of lesbian, gay, bisexual, and transgender people through their interest sharing within and outside lesbian, gay, bisexual, and transgender groups. Since the 1980s, research regarding lesbian, gay, bisexual, and transgender communities has focused on mental ill-health, with far less research attention on lesbian, gay, bisexual, and transgender well-being. I was curious about this research gap, especially given the exponential growth of lesbian, gay, bisexual, and transgender groups over the same time frame. Qualitative methods are appropriate in exploratory research in areas that are under-researched or subject to misconceptions. This case study provides an account of using insider ethnography, a method considered particularly effective in providing a rich, more nuanced picture of the meanings, understandings, and experiences of a social group. The core data collection method of in-depth interviewing facilitates participants to direct the interview as a “conversational partner.“ I also illustrate the critical role of gatekeepers in ensuring diverse representation of the breadth of interests through access, recruitment, and sampling. This case study identifies the need to adopt a reflexive process to critically evaluate researcher beliefs and assumptions in recognition that bias is part and parcel of the research process and relationships. Self-reflection on interviews is identified as critically important, and memo writing is highlighted as pivotal to the research project. At the heart of the case study is an emphasis on enhancing insider ethnography in problematizing the dominant discourse and universal “at risk” representation of lesbian, gay, bisexual, and transgender mental ill-health. This is essential given the breadth of lesbian, gay, bisexual, and transgender lived experience.