This one-day workshop will encourage the emergence of more critical and socially oriented perspectives to a data-driven life. We adopt a focus on how data mediates relationships personal, professional, across social networks and cross-culturally to consider the social and cultural implications of quantified lifestyles. At the workshop, attendees will engage in panel discussions, and a series of 'speed-dates' to develop a catalogue of compelling relationships with data, which exemplify the social nature of personal informatics tools, and the opportunities and challenges for design.