Relationship health is shown to be important for both individual well-being and entrepreneurial success. Given the number of hours that many adults spend at work each week, relationships at work matter. Mobile technologies and other factors are dramatically changing how and where people work. Increasing numbers of workers are drawn to the flexibility and geographic freedom of self-employment and independent work. Emerging from this trend are a number of unintended consequences. Some are welcome. Others are not. One consequence is the increased vulnerability of many independent workers to isolation or loneliness, as they run their businesses alone from home, or near strangers in a library or coffee shop. The relationship health of many is suffering. In response, the coworking movement has arisen with the recognition that the autonomy many independent workers seek does not exclude a desire for meaningful relationships and positive interaction with other productive workers. This paper examines connections between relationships, coworking and the field of positive psychology, and introduces three main propositions. First, it suggests that independent workers can use coworking spaces to support their personal and business relationship needs. Secondly, evidence is presented that coworking spaces appear to be creating environments that promote relationship health specifically, and individual and community well-being generally. Thirdly, it is proposed that the study of human and institutional thriving can both inform and be informed by the practices being implemented at coworking spaces, in order to cultivate and elevate successful communities of flourishing individuals.