This article aims to provide understanding of how direct care workers (DCWs) in assisted living facilities (ALFs) interpret their relationships with residents and to identify factors that influence the development, maintenance, quality, and meaning of these relationships. Qualitative methods were used to study two ALFs (35 and 75 beds) sequentially over seven months. Researchers conducted in-depth interviews with 5 administrative staff and 38 DCWs and conducted 243 hours of participant observation during a total of 99 visits. Data were analyzed using a grounded theory approach. Results showed that the emotional aspect of caregiving provides meaning to DCWs through both the satisfaction inherent in relationships and through the effect of relationships on care outcomes. Within the context of the wider community and society, multiple individual- and facility-level factors influence DCW strategies to create and manage relationships and carry out care tasks and ultimately find meaning in their work. These meanings affect their job satisfaction and retention.