Pathways to and from homelessness were examined from the perspective of people who were both employed and homeless in Calgary, Alberta. Based on data collected through semi-structured open-end interviews (n = 61) with employed homeless people (N estimated at 2,400), we found that respondents identified aspects of five predominant social relationships that had the greatest impact on their present homeless situation: relationships with friends and family, acquaintances in shared accommodation, landlords and employers, other homeless people, and the social service delivery system. The findings provide a model for beginning to understand the complex social communities in which homelessness exists. Further research needs to explore the relationship between service providers and individuals' other social relationships and the role those can play in finding a pathway from homelessness.