Temporomandibular Disorder(s) (TMD), a common cause of chronic pain affecting the face and jaw, profoundly impacts interactions as fundamental to human existence as smiling, laughing, speaking, eating, and intimacy. Since landmark anthropological research on TMD in the 1990s, considerable changes have occurred in the way TMD is thought about and responded to. Knowledge about TMD among dentists and physicians has increased since publication of the Research Diagnostic Criteria (RDC-TMD), and a well-funded TMJ association now advocates for research and support of the condition. On the other hand, concerns in the medical world about increases in chronic pain and associated risks of misuse of pain medications have increased. Physicians are trained to perform a gatekeeper role, preventing those patients at-risk of becoming drug abusers from gaining access to opioid pain medications. These differing contextual factors and my focus on a group of participants drawn from a complementary and alternative medicine (CAM) trial, rather than from a pain clinic, provide an expanded and updated view of TMD. I present analyses of semi-structured, open-ended interviews with 44 participants interviewed multiple times over the course of their participation in an NIH-funded trial evaluating Traditional Chinese Medicine (TCM) for TMD. In contrast to earlier studies of participants who were consumed by an endless search for diagnosis and treatment, these participants were largely focused on coping and "just dealing with" the daily experience of severe pain. Three articles comprise the body of work presented in this dissertation. Topics include the Works of Illness, the Paradox of Hope, and the construction of moral identity through consumption of over-the-counter (OTC) medications. First, using a "works of illness" framework, I draw attention to the considerable work sufferers undertook to manage competing demands of social and physical risk imposed by chronic pain. I refer to these forms of work as the work of stoicism and the work of vigilance and identify double binds created in contexts that call for both. Multiple voices in the narratives of sufferers are highlighted as essential to the construction of a positive identity in the face of illness. In more in-depth exploration of the work of hope, hope is revealed as a fundamental and paradoxical aspect of autobiographical work. I describe multiple forms of hope in a typology of ways of hoping and raise as an issue the manner in which the paradox of hope--keeping hopes in check while also avoiding despair-- intersects with participant expectations in the trial. I suggest this may have an impact on the placebo effect. Trade-offs between physical harm reduction and reducing potential harm to one's identity produce narratives of harm justification as pain sufferers work to describe their use of OTC medications as minimal and responsible. Sufferers in this study, describing medications as "just over-the-counter" or "not real pain medication" distanced, themselves from association with the addictive potential of prescription pain medications. Participants avoided harm to their identities by consuming OTC pain medications as idioms of self-care. This case study provides important lessons about the experience of chronic pain in the USA. While much attention has been directed at overuse and addiction to pain medication, less has focused on the experience of those soldiering through pain and navigating paradoxes between social and physical demands. This study also directs attention to anthropology's potential contribution to drug trials, to the necessity of studying hope as well as expectations, and to how both impact the placebo response.