Obesity has been linked to a wide range of health problems. Evidence suggests that overweight and obese (OW/O) women avoid or delay seeking medical care and routine health screenings, a choice that may result in poorer overall health. The objective of this study is to explore how an OW/O woman’s self-identity and her experiences in past medical encounters may affect her health-seeking behaviors. Twenty-three women who self-identified as being overweight (currently or in the past) were recruited using a flyer placed in a women’s exercise facility and through the snowball method. Each agreed to an audio-taped, in-depth, semi-structured interview. Interviews were transcribed and analyzed. This study employs multiple methods of analysis and multiple genres of representation of the data, an approach recently termed “crystallization.” Analysis of an autoethnographic narrative served as a guide for the generation of the research questions, which focused on how OW/O women conceptualize their identities in relation to their bodies, how their attitudes about their bodies may have impacted choices about seeking healthcare and their perception of their experiences within medical encounters, and what OW/O women believe to be potentially effective strategies for clinicians to adopt in caring for overweight patients. Interviews were scrutinized to identify story types using Arthur Frank’s well-established framework for the analysis of narratives of sudden life-threatening illness. Two additional story types, Reorientation and Acceptance, are proposed as potentially useful in analyzing stories of chronic health conditions. Grounded theory analysis was used to identify the factors that OW/O women perceive to contribute to their weight struggles, as well as to determine clinician attitudes and practices that OW/O women regard as effective and ineffective. Two emergent themes—othering and control—were discerned in the data and are discussed in terms of both how OW/O women are impacted by their weight and how practitioners can work to provide more effective care. An explanatory model linking social bias, personal identity, and medical interactions is proposed. Finally, a performance script is presented as a means of synthesizing and disseminating research findings.