Context. In the era of effective antiretroviral therapy, persons living with HIV/AIDS (PLWHA) are living longer, transforming HIV from a universally fatal disease to a serious chronic illness, warranting discussions between patients and their loved ones about advance care planning (ACP). Evidence is needed on factors associated with patients' likelihood to discuss ACP with loved ones. Objectives. To further characterize factors associated with successful ACP in PLWHAs with their loved ones, we examined associations between patients having ACP discussions with the need for assistance with personal care, chronic pain, life satisfaction, prior family disagreements over health care decisions, sex, age, and interference in daily routines due to memory problems. Methods. Data were from the Affirm Care study (N ¼ 370), which examined social and environmental factors associated with health outcomes among PLWHAs and their informal caregivers. Results. Slightly more than half of respondents discussed ACP with loved ones (57%). In adjusted analysis, higher levels of chronic pain (odds ratio [OR] ¼ 2.09, P ¼ 0.045), needing assistance with personal care (OR ¼ 1.63, P ¼ 0.023), greater life satisfaction (OR ¼ 1.02, P ¼ 0.002), prior family arguments over health care decisions (OR ¼ 2.80, P < 0.001), and female sex (OR ¼ 2.22, P ¼ 0.001) were associated with higher odds of discussing ACP with loved ones, whereas age, drug use, education level, depression, and memory problems were nonsignificant. Conclusion. These results suggest that interventions to increase ACP among PLWHAs and their loved ones should target males. The findings also suggest PLWHAs with chronic pain, the need for assistance with personal care, and those with a history of prior family arguments over health care decisions may be primed for ACP.