Aims/Objectives: Research has highlighted that men and women self-manage their diabetes differently. Greater understanding of these differences could inform educational programmes. The aim of this study was therefore to investigate how men and women diagnosed with Type 2 diabetes (≤55 years of age) self-manage their diabetes alongside their other life roles. Methods: Semi-structured individual interviews were conducted (n = 18). Recorded data were transcribed and analysed to detect emerging themes. Descriptive statistics were used to describe the sample. Results: Differences in how males and females self-manage their condition were identified. Family eating habits were more likely to change in response to male diagnosis and education, whilst females were likely to change their own diet, but minimise impact on family habits. Differences also existed within the sample regarding their understanding of their condition even after attending structured diabetes education. A key feature among this sample was the number reporting depression. Conclusion: The results indicate that education should be tailored to a greater degree to reflect the needs, capacity and circumstances of men and women. Depression may also impact upon the patients’ ability to engage with education, and may be a barrier to effective assimilation and understanding. While the results of a qualitative study cannot be generalised, there are messages for those designing diabetes education programmes, reflecting differing behaviours across genders. Further research examining needs of males and females in relation to their diabetes is essential, including the development of personalised, even gender specific education programmes.