The sustainability of food is a significant global concern with a drastic change required to mitigate complex social, environmental, and economic issues like climate change and food security for an ever increasing population. In this article, we set out to understand the place of food in people's lives, their mundane yet surprisingly complex ways of sourcing their food, and the processes of transition, past and ongoing, that shape these choices. Our goal is to understand the potential role for digital interactions in supporting the various ways that food consumption can be made more sustainable. To inform this exercise, we specifically set out to contrast the journeys of committed sustainable “food pioneers” with more conventional mainstream consumers recruited in branches of a UK supermarket. This contrast highlights for both groups the various values, and “meaningfulness” attached to foods and meals in people's lives, and suggests ways in which food choice and pro-sustainable practices can be supported at least in part by new digital technologies.