This case study explores the methods used in a study of how older people who live at home alone interact with, and attach meaning to, food. In this project, we designed, piloted, and distributed 5-day food diaries to 10 older people living on their own. We conducted pre- and post-diary interviews alongside the diary entries to gather additional qualitative data. The following account provides real-life examples of the highlights and practical challenges faced in this study involving diaries to elicit data on food practices. It outlines the potential of diaries to capture the social and symbolic dimensions of food consumption, which is often sidelined to nutrition. It further draws attention to the flexible nature of diaries and how they can be adapted to specific groups—in this case, older people. However, the case study also demonstrates the various ways in which participants engage with food diaries and describes how this study coped with outcomes such as diary non-completion and respondent innovation. In doing so, it appraises the advantages and shortcomings of “open” versus “structured” diary designs and discusses how even “structured” diary designs are sensitive to unexpected interpretations.