Social prescribing is a non-clinical approach to addressing social, environmental, and economic factors affecting how people feel physical and/or emotionally. It involves connecting people to “community assets” (e.g., local groups, organizations, and charities) that can contribute to positive well-being. We sought to explain in what ways, for whom, and why the cultural sector can support social prescribing with older people. We conducted semi-structured interviews with 28 older people (aged 60+) and 25 cultural sector staff. The following nine concepts, developed from interview data, progressed the understanding of tailoring cultural offers, which came from our previous realist review—immersion, buddying, café culture, capacity, emotional involvement, perseverance, autonomy, elitism, and virtual cultural offers.Through tailoring, we propose that older people might experience one or more of the following benefits from engaging with a cultural offer as part of social prescribing—being immersed, psychological holding, connecting, and transforming through self-growth.