Developments like COVID-19 and Black Lives Matter have exposed the distinctive challenges to grief in our contemporary context. This article invites readers to see grief as a choice that leads to revelations about the depths of human connectedness that need to be recognized as integral to the moral life. After studying lament in Black Lives Matter, we focus on what it means to grieve by pursuing three main topics: the Bible and grief, anticipatory grief, and learning to move forward in grief. We conclude by offering five different passageways of grief.