Background: Pregnancy loss is a profoundly traumatic event that can leave lasting emotional and psychological effects. While subsequent pregnancies are often thought to ease grief, many women continue to experience unresolved distress. Objective: This pilot study examined demographic, reproductive, and psychosocial correlates of grief intensity after pregnancy loss among women in the third trimester of a subsequent pregnancy. Methods: Twenty partnered women who had experienced a prior pregnancy loss, now beyond the gestational age of that loss, were recruited from childbirth classes. Participants completed standardized measures of grief, social support, spirituality, post-traumatic stress, and depression. Results: Grief intensity was significantly related to education, gestational age at loss, perceived social support, and symptoms of post-traumatic stress and depression. Conclusions: Findings suggest that while subsequent pregnancies may soften grief, they have limited impact on PTSD and depressive symptoms. Targeted interventions remain critical for healing.