Purpose: Widowhood is among the most distressing of all life events, resulting in both mental and physical health declines. This paper explores the dynamic relationship between physical health and psychological well-being among recently bereaved spouses. Design and Methods: Using a sample of 328 bereaved persons who participated in the “Living After Loss” study, we modeled trends in physical health, somatic symptoms, and psychological well-being over the first year and a half of widowhood. The primary focus is whether physical health at the time of widowhood modifies psychological well-being over time. Results: There were considerable somatic symptoms during the earliest months of bereavement but no major health declines over the first year and half of bereavement. Those in poor health had initially higher levels of grief and depressive symptoms, but the trajectories or changes over time were similar regardless of health status. Those with poor health at the time of widowhood had significantly higher risks of complicated grief and major depression disorder. Implications: Bereavement requires physical and emotional adjustment, but the psychological trajectory of bereavement may be somewhat universal. Bereavement support ought to include a focus on self-care and health promotion in addition to emotional support, especially because those with poor health initially may be most susceptible to prolonged and intense clinical distress.