The United States, indeed the world, struggles with a serious obesity epidemic. The costs of this epidemic in terms of healthcare dollar expenditures and human morbidity/mortality are staggering. Surprisingly, clinicians are ill-equipped in general to advise patients on effective, longitudinal weight loss strategies. We argue that one factor hindering clinicians and patients in effective shared decision-making about weight loss is the absence of a metric that can be reasoned about and monitored over time, as clinicians do routinely with, say, serum lipid levels or HgA1C. We propose that a dietary quality measure championed by the USDA and NCI, the HEI-2005/2010, is an ideal metric for this purpose. We describe a new tool, the quality Dietary Information Extraction Tool (qDIET), which is a step toward an automated, self-sustaining process that can link retail grocery purchase data to the appropriate USDA databases to permit the calculation of the HEI-2005/2010.