NAFLD is closely related with the metabolic syndrome (MetS) and increased risk of cardiovascular disease. Liver fat associates with post-prandial hypertriglyceridemia, potentially contributing to triglyceride-enrichment of high-density lipoproteins (HDL-TG), and subsequent HDL dysfunction. We assessed liver fat by MR spectroscopy, and its association with HDL physiochemical properties, and endothelial function, measured as flow-mediated dilation (FMD), before and following three consecutive meals, in 36 men with type 2 diabetes mellitus (T2DM), with the MetS, and controls. Plasma triglycerides increased significantly following the meals (P <.001). Fasting HDL-TG was highest in T2DM, relative to MetS and controls (P =.002), and increased post-prandially in all groups (P <.001). HDL function was negatively associated with HDL-TG following three meals (r = −.32, P<.05). Liver fat associated with HDL-TG after three meals (r =.65, P <.001). HDL-TG was independently associated with FMD following three consecutive meals (r = −.477, P =.003). We conclude liver fat is associated with post-prandial HDL-TG enrichment which was closely related with endothelial and HDL dysfunction.