As patient-reported outcome measures (PROMs) increasingly become key outcome indicators in health care, there has been growing concern about the potential negative consequences that could result when interpretations are being made to inform clinical and policy decisions. Therefore, we explored theoretical issues, assumptions, and consequences of using PROMs from a philosophical point of view. Our analysis of the literature was informed by Gadamerian hermeneutics, which emphasizes the dialectical processes that occur during interpretation, to provide insights as to how different users interpret and use standardized questions about health and quality of life. We structured our consideration according to three tenets of using PROMs (1) the use of PROMs involves the interpretation of contextual elements (2) interpretation of PROMs is an ongoing dialectical interaction and (3) the use of PROMs involves openness and reflexivity. These findings suggest that hermeneutics provides a useful approach to examining the complexities of measuring patient-reported outcomes by attending to the perspectives of different users (e.g., patients, clinicians, administrators, and policy-makers) at the micro-, meso-, and macro-levels and the broader socio-historical and economic situation. Because PROMs can have different meanings and are used for different purposes, we propose that hermeneutics be used as a lens to ask reflexive questions about the problems of measurement and open a pluralistic dialogue with respect to the way we use PROMs and the interpretations we make of the findings that derive from our studies.