Several studies have shown beneficial associations between tea consumption and bone mineral density (BMD) and fracture risk. Current investigations into potential mechanisms of benefit are focused upon the F and polyphenol components of tea. However, previous studies have pointed towards caffeine consumption as a potential risk factor for low BMD and high fracture risk. Tea, therefore, represents an interesting paradox as a mildly caffeinated beverage that may enhance bone health. Fruit and vegetable intake has also been associated with BMD, and it is now apparent that several fruit and vegetable components, including polyphenols, may contribute positively to bone health. Evidence surrounding the function(s) of polyphenol-rich foods in bone health is examined, along with more recent studies challenging the relevance of caffeine consumption to in vivo Ca balance. Plant foods rich in polyphenols such as tea, fruit and vegetables, as significant factors in a healthy diet and lifestyle, may have positive roles in bone health, and the negative role of caffeine may have been overestimated. The present review covers evidence of dietary mediation in positive and negative aspects of bone health, in particular the roles of tea, fruit and vegetables, and of caffeine, flavonoids and polyphenols as components of these foods. Since the deleterious effects of caffeine appear to have been overstated, especially in respect of the positive effects of flavonoids, it is concluded that a reassessment of the role of caffeinated beverages may be necessary.