This qualitative study employed a cross sectional focus group design to explore how older gay men living with HIV, experience, perceive, and engage with advance care planning (ACP). Seven gay men 50+, residing in Montreal, Canada, participated in a focus group that was audio-recorded, transcribed, and thematically analyzed. Findings suggested that social isolation, preoccupations with day-to-day living, and managing disclosures related to sexual orientation and HIV status created barriers to these men's capacities to think about let alone talk about future care. These findings challenge current conceptualizations of ACP, which position reflection as an individual process that precedes allocating a decision-maker and communicating care preferences. Analyses further revealed that relational connections helped create a space where ACP could occur for participants. Hence, improving the uptake of ACP amongst older gay men with HIV may require interventions that embed such discussions into broader programs aimed at building support and community.