Objective: Little research exits on how grief and loss contributes to the homelessness of older male adults. This paper will review the available literature on grief and loss and homelessness and explore how grief and loss has factored into the experiences of homelessness for 20 older adults at The Good Neighbours Club. Methods: 20 members were recruited from The Good Neighbours Club to voluntarily participate in a half hour in person qualitative interview with the club social worker. The interviews explored members’ successes and challenges, relationships and supports, career, housing, impact of grief and loss, life lessons, and life improvements with both their personal lives and the drop in centre. Results: Grief and loss was reported to significantly impact the majority of men who were interviewed for this study. According to these older adults, separation and divorce, injury on the job, substance use, insecure employment and financial problems resulting from job loss were instrumental factors which led many of them to become homeless as older adults. Conclusion: There is little research available on this topic and future research needs to be done to further investigate how grief and loss contributes to homelessness in older men. It appears as though many older adults who have become homeless later on in their lives experienced significant losses throughout their lives. This coupled with insecure finances and employment and ongoing substance use issues have led them into a cycle of homelessness and poverty which has been difficult to both navigate through and successfully overcome.