The aim of this paper is to explore the difficulty faced by consumers in complying with health-related dietary guidelines, focusing on those guidelines that consumers find it more/less difficult to meet and the factors driving the ability to make associated dietary changes. Participants reported self-assessed compliance with 12 dietary recommendations predominantly directed at reducing the risk of heart disease. The difficulty of complying with each of the dietary guidelines was measured using a Rasch model, while the determinants of ability to comply with the dietary recommendations as a whole were identified using regression analysis. The more difficult dietary recommendations included limiting consumption of red meats and consuming the recommended daily intake of fruits and vegetables. Attitudinal variables associated with food, nutrition and health, perception of cholesterol risk and a range of socio-demographic variables, including age, gender and education, were significant determinants of person ability to comply with the dietary recommendations. The results show that there are significant differences in the difficulty faced by consumers in complying with particular dietary recommendations, while there is substantial variation in the ability to eat a healthy diet across participants.