Healthy eating often depends on individuals’ nutritional knowledge and their ability to quickly gauge nutritional composition of meals. However, both of these tasks present considerable challenge, and computing tools meant to assist in these tasks continue to be cumbersome and labor-intensive. In a pilot study, we investigated the potential of promoting nutritional literacy with social computing platforms by helping individuals compare their own meals with meals captured by others. We compared this holistic comparison approach with a more traditional method that requires mental decomposition of a meal into ingredients and estimating their portion sizes in a controlled experiment with crowd workers on Amazon Mechanical Turk. Based on the results of this study, we have identified new approaches for incorporating socially generated data, crowdsourced evaluations, and gameful components into smartphone apps to increase engagement and fun.