With ever-increasing costs, uneven access, and mediocre quality, the United States healthcare system is underperforming relative to the rest of the world. One major driver of this inefficiency is the flagrant overuse and underuse of healthcare services. In particular, the treatment of chronic pain patients plays a major role, in that the care of these 100 million Americans is poorly-coordinated, expensive, and ineffective. The present study sought to identify how the type of pain (continuous, intermittent, affective, & neuropathic), as well as the intensity of these pain components, are linked with risk preferences with respect to health and financial decisions. To this end, a demographic survey, a 22-item pain questionnaire, a gambling choice question, and a self-reported risk assessment were administered electronically to 106 Chronic Pain patients and 109 individuals representative of the general population via the Survey Monkey Recruitment Platform. After performing Tobit regressions with robustness checks, it was found that the amount and intensity of neuropathic pain significantly increased risk-seeking preferences in health matters. In addition, demographic factors predicted risk preferences, but these factors varied with respect to domain. By better understanding chronic pain patients’ risk preferences, healthcare providers and policymakers can formulate strategies to encourage appropriate interventions at key points in the care of a patient. In the context of the opioid abuse epidemic, it may be best to take a deeper look into an individual’s pain as well as demographics before presenting patients with risky treatment options.