We conduct a detailed investigation of the relationship among the obesity rate of urban areas and expressions of happiness, diet and physical activity on social media. We do so by analyzing a massive, geo-tagged data set comprising over 200 million words generated over the course of 2012 and 2013 on the social network service Twitter. Among many results, we show that areas with lower obesity rates: (1) have happier tweets and frequently discuss (2) food, particularly fruits and vegetables, and (3) physical activities of any intensity. Additionally, we provide evidence that each of these results offer different and unique insight into the variation of the obesity rate in urban areas within the United States. Our work shows how the contents of social media may potentially be used to estimate real-time, population-scale measures of factors related to obesity.