This article reports on a qualitative study to investigate what bereavement means to older people. Drawing upon 80 in-depth interviews collected from eight British and Australian retirement communities, our study revealed that facing bereavement while ageing includes experiences of losing both others and the wholeness of the self. Core themes identified how the experience of losing others can be compounded by ageing-related challenges, undermining older people’s defence from bereavement and frustrating their fundamental meaning and being. The older people’s dynamic responses were also captured, highlighting the importance of supporting their agency to deal with the deeper pain of loss. By extending the concept of bereavement in later life, we also called for a more grief literate culture to mitigate the multifaceted and often deeper distresses of bereavement that older people may face alongside ageing.