This report presents the findings of extensive research about employable singles on social assistance undertaken by Toronto Employment and Social Services, in partnership with the Ontario Centre for Workforce Innovation. Drawing on data from 69,000 singles who were receiving social assistance in Toronto in 2016, and 51 interviews with randomly selected participants, the report highlights these individuals’ characteristics, their complex needs, and the barriers they face in moving off social assistance and into employment. Complementing the quantitative analysis, the interviews provide important insights into the daily realities of participants’ lives and their journeys on and off assistance.