The endothelium, a continuous monolayer of cells that surrounds blood vessels, has a variety of physiological roles. Chronic exposure to psychological and physical stress, oxidative stress, and inflammation activates the endothelial signaling cascade, resulting in vascular dysfunction such as vasospasm, thrombosis, and abnormal vascular proliferation. Aging is also a significant factor in vascular dysfunction, mainly developing structural and functional changes in the endothelium. The molecules involved in endothelial dysfunction are typically angiopoietin-1 (Ang-1), Tie2, and tight junction proteins. Ang-1, an oligomeric-secreted glycoprotein, is required for the correct organization and maturation of newly-formed vessels. Ang-1 binding to tyrosine kinase receptors Tie-2 leads to the phosphorylation and activation of multiple signaling pathways related to vascular permeability. Endothelial junctions are another vital target of Tie-2 activation. Nutrition and food are closely connected with vascular dysfunction and permeability. The caloric restriction prevents age-related declines in endothelial function. Dietary patterns that prioritize moderate intake of fruits and vegetables, whole grains, low-fat dairy products, and lean meats improve endothelial function in the elderly. Natural products such as Centella asiatica, Pueraria montana, and Piper retrofractum have also been shown to help inhibit endothelial dysfunction. This review provides an update on aging-related vascular dysfunction and the role of food and nutrition.