New Zealand’s population, like the global population, is ageing. An important element of successful ageing is the maintenance of optimal nutritional status, which is linked to general health and quality of life. The purpose of this mixed methods study, guided by qualitative descriptive methods, was to identify barriers to healthy eating in a group of older single-living New Zealand men. Understanding the men’s perspectives on meal procurement and preparation, in essence walking in their shoes, was a key part of identifying barriers to healthy eating. A cohort of 12 men participated, each completing a semi-structured interview as well as a nutrition knowledge and nutritional risk assessment questionnaire. Data from the semi-structured interviews was analysed using a general inductive approach. The results of the questionnaire were used to enrich description in this mixed methods study. Three core themes emerged from the data which were ‘Individual Circumstances’; ‘Nutrition Knowledge and Skills’; and ‘Food-Related Values’. Potential barriers to healthy eating, in terms of individual circumstances, were limited finances, limited mobility and a lack of personal transport. These barriers were partially ameliorated by effective, reliable social and support networks. A diverse range of shopping, cooking and gardening skills, as well as nutrition knowledge, existed amongst the men. Poor nutrition knowledge and limited cooking skills were possible barriers to healthy eating. Strong beliefs the men held about how food procurement and preparation should occur, termed food-related values, were also potential barriers to healthy eating. Values identified were ‘the importance of healthy eating’; ‘structure in food-related activities’; ‘convenience’; and ‘like it or not, it has to be done – shopping and cooking’. Depending on the prioritisation of values by the individual, they could develop into barriers. For example, prioritising ‘convenience’ over ‘the importance of healthy eating’ led to decisions that negatively impacted dietary intake. This study highlighted the diversity of experiences, circumstances, skills and priorities of older single-living men. Interventions aimed at improving the dietary behaviours of older single-living New Zealand men must recognise the heterogeneity of this population and support the values they hold in regards to food-related activities.