In this article we argue that despite methodological and analytical advancements in the field of social class research, these developments have not led to a wholehearted discussion about class positionality and situatedness in relation to interviewer–participant dynamics. Despite—or perhaps due to—this methodological gap, there remains an unspoken expectation that class matching, particularly when investigating working-class groups and practices, is desirable as it engenders empathy on the part of the interviewer which allows for openness on the part of the participant. The team of four interviewers reflect upon their varying experiences of conducting interviews about class with a group of middle- and working-class students at university, arguing that even if class matching between participant and researcher were possible, shared class position does not necessarily equate with similar life experiences, or enable a strong rapport nor a more ethical analysis or understanding of working-class people's lives. We explore some of the complexities regarding the class-related positions of the researchers and the participants and consequently advocate that class researchers engage in reflexive practices in order to explore the myriad ways in which the researcher's own class history and current class position both advantage and disadvantage the research process, often in unpredictable ways.