Loneliness is associated with poorer health practices and fewer health-promoting behaviors and may be associated with greater use of the health care system. Given national conversations about aging in context, this investigation explored the relationship between perceptions of loneliness in 2008 and prostate cancer screening participation in 2008 and 2012. Using data from the Health and Retirement Study, authors examined the relationship between loneliness and prostate cancer screening in 2008 and 2012 among Black, Hispanic, and non-Hispanic White men, ages 50 to 74 years (N = 4,875) using a series of logistic regression models. Findings indicate that White men who indicated being more lonely were less likely to participate in screening in 2008 and 2012. For Black men, there was a reduced likelihood of screening in 2012 with one aspect of decreasing loneliness. Social workers have unique training focusing on the person-in-environment model. Use of the person-in-environment model can help health care providers understand men’s experiences and their feelings or needs related to cancer screening participation. Given the lack of focus on men’s health-promoting behaviors related to loneliness, this study provides formative data to test interventions to increase the well-being of older men.