This case study discusses an aspect of the first author’s PhD research that examined gay and bisexual men’s accounts of sex and diabetes. Semi-structured interviews were conducted with non-heterosexual men living with diabetes both online and face-to-face. In this case, we discuss some of the advantages and disadvantages of these two types of interviews and shed light on some of the unexpected events that occurred during data collection. We then consider how some of these incidents may relate to the interviewer’s “outsider” and “insider” positions within the research and discuss how the researcher’s personal similarities and differences with participants may affect research. We then turn to the sensitivities of discussing the issue of sexual difficulties with the participants and the importance of following the participants’ concerns within the interview. We end by reflecting on how the research emerged both from the researchers’ prior agenda and the participants’ concerns. The need for caution and care when representing accounts of illness, particularly those from marginalized groups, is highlighted.