For most people, following the death of a loved one, meaning is made in the context of a long, fulfilled life. One exception to this is the instance of perinatal loss, which can be an inconceivable experience, where loved ones and professionals alike may have trouble making sense of “why this happened.” In this unthinkably painful and complex experience, many parents grieve deeply throughout their lifetime. The shockwaves from this death can impact the mourning process and worldview of multiple generations within a family. Social supports often incorrectly assume that the grief will be proportional to the length of their time with the fetus or baby. However, through quality bereavement care, a parent’s sense of self can be restructured with a potential for positive growth after the loss. Care providers have an opportunity to provide education and support to families in need. This chapter aims to address the multifaceted nature of the grieving process, common grief theories, how they apply to the perinatal population, and a suggested approach to working with families. It will explore the resilient capabilities of three bereaved families to provide insights on how clinicians can care for those who have experienced a perinatal loss.